sailboat cruising chesapeake bay

Free Shipping to Lower 48 States! Fast Delivery, Many Boats in Stock! LEARN MORE

Top 13 Chesapeake Bay Cruising Destinations

Aug 26, 2020

One of the big advantages of owning an inflatable boat is the ability to travel where you want, whenever you want, to enjoy a day of sailing. If you're a Maryland, Virginia, or D.C. resident, you have access to one the world's best cruising destinations, the Chesapeake Bay.

From fishing and national parks to delicious food like crabs and oysters, the Chesapeake Bay has a lot to offer. Covering over 4,000 square miles, there is plenty to explore. Below you'll find the top 13 Chesapeake Bay cruising destinations.

1. St. Michaels

Located on Maryland's Eastern Shore, St. Michael's, Maryland has plenty to offer despite being home to a little over 1,000 people. Home to the Chesapeake Bay Maritime Museum , several art galleries, restaurants, and other historic landmarks, St. Michaels is also a prime cruising destination. Located on the water, St. Michael's is a perfect place to access the Chesapeake and it offers up some wonderful views.

2. Galesville

Located on the western shore of the bay, Galesville is a small town that sits along the West River. A steamship line in Galesville used to connect Annapolis and Baltimore, and the town was once home to many Chesapeake Bay Watermen. It is now a hot spot for pleasure boating and home of the West River Sailing Club and Hartge Yacht Harbor

Located along the Tred Avon and Choptank Rivers, Oxford, Maryland is home to the Oxford-Bellevue Ferry, the Tred Avon Yacht Club, and the Oxford Museum . The ferry is believed to be the oldest privately owned ferry, with service dating back to 1836. In addition to its local attractions, Oxford access to the Tred Avon and Choptank makes it a great cruising destination for sailors and boaters alike.

Located 40 minutes south of Annapolis, Deale, MD provides many scenic views of the Chesapeake, making it a popular destination with boaters. Home to waterfront bars and open-air crab houses, Deale is perfect for anyone looking to hit the open water for the day and then enjoy a good meal afterwards.

5. Solomons Island

Located at the mouth of the Patuxent River, Solomons Island was the home of many 19th century shipyards that supported the local fishing economy. Today, Solomons Island is home to many marinas, seafood restaurants, the Calvert Marine Museum , and the Annmarie Sculpture Garden & Arts Center . Its position along the waterfront make it a prime destination for cruising.

6. Rock Hall 

The jewel of the Upper Eastern Shore, Rock Hall, MD is a picturesque cruising destination. Serving as the hub for Kent County's maritime industry, Rock Hall is home to the Rock Hall Yacht Club, over a dozen marinas, various charters, boat rentals, and more! A day of cruising in Rock Hall will give you access to beautiful scenery and plenty of open water to explore.

7. Chestertown

Located along the Chester River, Chestertown was once one of the six Royal Ports of Entry and considered Maryland's second leading port. Today, Chestertown is home to Washington College, a number or restaurants and historic attractions. Offering a wide range of scenic and historic sailing views, Chestertown is a perfect location for day cruising.

8. Kent Island

The largest island in the Chesapeake, Kent Island, is nestled between Annapolis and the Eastern Shore of Maryland. The Cross Island and South Island trails provide plenty of outdoor activities across the island. For those looking to cruise the open waters, Kent Island offers unique access to the Eastern Bay, Chester River, and the heart of the Chesapeake Bay itself.

9. The Wye River

With easy access to fishing and crabbing destinations, the Wye River is a favorite cruising destination for many. Add in the Wye Island Natural Resource Management Area, and you have a perfect destination for cruising and exploring the outdoors.

10. Baltimore

Baltimore's Historic Inner Harbor is the mouth of the Patapsco River. With access to a number of marinas, the Inner Harbor is a great launch point for day cruising. Enjoy views of historic Federal Hill and Fort McHenry in the Harbor, and as the Patapsco opens up into the bay, you'll find additional outdoor destinations such as North Point State Park and Fort Smallwood Park.

11. Annapolis

Sometimes referred to as the Sailing Capital of the U.S., Annapolis is home to various boat shows, the Naval Academy, and the National Sailing Hall of Fame. Its position along the South River, Severn River, and the Chesapeake Bay make it a great launch point for cruising.

12. Washington DC

The beautiful Potomac River runs directly through the Nation's Capital, making Washington, D.C. a prime destination for sailors. With access to historic views in the heart of D.C. to a variety of parks and outdoor destinations, D.C. is a great place to spend a day out on the water.

13. Havre de Grace

Sitting at the mouth of the Susquehanna River and the head of the Chesapeake, Havre de Grace is uniquely positioned to several state parks and scenic views including Elk Neck State Park and Susquehanna State Park. With easy access to the water and the outdoors, Havre de Grace is a worthwhile destination for anyone looking to explore the bay.

Sign Up for Our Newsletter

Receive exclusive offers, and be the first to know about upcoming events, demos, sales, and discounts.

We sail April 19, 2024 to Nov 3, 2024

Sail Selina II

Relaxing chesapeake bay sailing tours, sailboat rides & sightseeing boat trips in st. michaels, md, we sail april 19,2024 to nov 3, 2024, clean & safe, thank you for supporting small business, our popular st michaels maryland sailing charters and relaxing chesapeake sailboat cruises.

• Most Popular
• Calendar Daily
• User All ages
• Users 6 People
• Hour Glass 2 Hours

2 Hour Relaxing Chesapeake Day Sail

Want to relax? Join our friendly crew and learn about St. Michaels while cruising in a comfortable well-maintained historic sailboat on the Chesapeake Bay. Enjoy the sun on your face and the wind in your hair as you sit back, relax, and enjoy outdoor scenery on your personalized sailing boat tour!

Chesapeake Bay Champagne Sunset Sail

Experience a breathtaking Chesapeake Bay sunset while savoring a glass of Champagne or handcrafted beer or wine on this romantic St. Michaels, MD sunset cruise. Book now to embark on an unforgettable journey that’s perfect for couples looking for a unique and romantic date night activity.

Moonlight Cruise

Enjoy free Champagne while taking in the breathtaking beauty of a sunset or the rising of the moon on Chesapeake BY aboard this romantic Moonlight Cruise!

• User Ages 21+

St. Michaels Wine Tasting Cruise

Come aboard Sail Selina II in St Michaels MD and learn the basics of wine tasting and sample great vintages with Capt. Iris and her crew during this 2hr outdoor excursion.  Our wine cruise is just an hour from Annapolis, making it the perfect day trip.

Beer Tasting Cruises

Looking for a fun and refreshing way to quench your thirst with a cold beer while exploring the St Michaels area? Sit back and enjoy some great Maryland Craft breweries aboard the Selina II!

Private Sailing Lessons

Embark on an unforgettable sailing adventure with our seasoned team aboard the historic yacht Sail Selina II. Experience the freedom and exhilaration of sailing while learning new skills and building confidence on the water. This introduction to the basics that will transform the way you connect with mother nature.

• User Adults only

Marriage Proposal Engagement Cruise

♥Getting engaged♥? Surprise your fiancé with a nautical wedding proposal on a private yacht with this Engagement Package. If you’re looking for a creative engagement on a boat this is a unique way to pop the question!

• Users 6 or More

Nautical Wedding Package

Looking at weddings on a boat? Get married in St Michaels MD on a sail boat and have an unforgettable nautical elopement or sailboat wedding ceremony aboard Sail Selina’s yacht! You have two wedding packages to choose from:  boat weddings are either a Ceremony Under Sail, or a Wharf-Side Wedding.

Sail Selina Swag

Sail Selina has perfected the art of sailing, and now we’re proud to introduce our collectable high-quality logo apparel that will have you looking as good as you feel on the water.

Best Relaxing Luxury Sail Boat Tours on Chesapeake Bay

Looking for a relaxing Saint Michaels, Chesapeake Bay boat tour? Want to get out on the water, unwind and spend some time in nature? If you’re wondering about things to do in St. Michaels MD or seeking top attractions in St. Michaels Maryland, look no further than the luxury sailing yacht Selina II. Unique, upscale, and exclusive, she limits her passengers to just 6 guests for an intimate taste of the history of sailing.

With freshly varnished mahogany, brightly polished brass, and comfortable seating, let Sail Selina II, the premier sailboat in St Michaels, MD, be your sightseeing charter boat. Hop aboard and experience another time and place.

Come join us outdoors on the water for a relaxing 2-hour sailing trip on this nostalgic river boat cruise. Your St Michaels, Maryland sailboat ride includes a personalized informative tour with our knowledgeable 1st-class captains and friendly crew. We know you’ll love all the boating trips aboard our meticulously-restored historic 1926 sailboat Selina II, including romantic sunset cruises, our super popular day sails, and our specialty outings like sailing lessons, wine tasting tours in St. Michaels MD, beer tasting cruises, moonlight sails and more.

For private sailing tours, the Sail Selina II is docked at the Harbour Inn & Marina in the heart of St Michaels, MD, a charming eastern shore town known for its wonderful seafood restaurants and quaint small-town feel.

If you are looking for day trips to St. Michaels Maryland or if you want a sailing charter on the Eastern Shore of the Chesapeake Bay, Sail Selina II’s relaxing sailboat trips are just 90 minutes from Philadelphia, Baltimore and Washington D.C. and just 60 minutes from Annapolis.

Outdoors in nature, our sailing boat offers your choice of a public or a private boat ride in one of the best places to sail. Chesapeake sailing is known for its beauty and gorgeous sunsets. Your sailboat charter includes a boat sail through the harbor and then out into the Miles River for spectacular views and sometimes even wildlife viewing like Osprey & Bald Eagles. This year there have even been porpoise sightings.

Looking to relax? We are the St Michaels MD harbor cruises to choose!

Learn more about the history of our sailboat and all the fun outdoor activities in St. Michaels, MD here:

The #1 Boat Tour in St. Michaels on TripAdvisor!

A friend was visiting from Baltimore and we went sailing last night for the sunset cruise. It was amazing, the sailboat was gorgeous, the Captain and her first mate were exceptional, and the beauty of the river was breath taking. I am so glad I discovered Sail Selina II, I will be taking many friends and family members on this beautiful adventure when they come to visit me in Easton. Thank you for a remarkable memory and such a beautiful experience.

A golden opportunity to sail on a captain owned historic wood yacht! It was a dog day of August with precious little wind, yet we enjoyed every minute of our trip. Captain Iris was a gracious host, passionate generational owner, not only captain but articulate professor of both sailing and ship building. We highly recommend sailing aboard the Selina ll. The crew is fabulous as well.

Hubby and I spent a sunset afternoon on Selina 2 with Captain Iris and first mate Jesus. We had a lovely cruise drinking champagne and listening to Captain Iris talk about St Michael and the history of her family sail boat. What I loved was she was mentoring a future captain in the making - a twelve year old from the area who wanted to learn more about sailing. This is so worth it and I very much encourage you to go!

My wife and I had a great time on this vintage sail boat. The Captain and First Mate were great hosts teaching us a lot about sailing and the history of the bay at the same time. Loved that the boat holds only six guests at a time, only four aboard for our trip, making it a very intimate experience!

The two hour cruise In the company of Captain Iris, Crewman Chris, and four other guests provided the best evening of our August vacation. The generous hospitality (nice selection of wine and beer if champagne was not your preference) was supplemented by the unexpected and pleasant opportunity to observe several races and Captain Iris was generous with her knowledge of sailing the Tred Avon areas of the Chesapeake. The Salina II will see us again when we return.

Took a moonlight cruise on the Sail Selena II. Had a lovely evening star gazing, sipping wine, chatting with the other couple aboard. Cap’t Iris and her ever so sweet (and personable) first mate were both kind and knowledgeable. We enjoyed the evening immensely. We would recommend this outing without hesitation. Such a great experience!

Being a motor-head all of my life never really let me get the deep appreciation of the sea as I experienced when I sailed on the Selina II. To cruise along with nothing but the sound of the waves, wind and seagulls was a truly eye opening experience for me. Captain Iris was absolutely enchanting with the stories of Saint Michaels and her beloved Selina II. The cruise was intimate with only 2 other couples and was an experience I will long remember.

Captain Iris runs a fabulous operation out of St. Michaels. This was our first time visiting the town and this was such a great way to experience St. Michaels and the Chesapeake. The Sunset Champagne cruise was fun and intimate as only 6 people maximum. The two other couples we met were so sweet. Sail Selina II is a must do in St. Michaels!

Why Sail Selina II?

Rated #1 on tripadvisor.

When looking for things to do in St Michaels MD, o ur reviews tell the story! Limited to just six guests, Sail Selina II is ranked the #1 Maryland sail boat tour in St. Michaels and has been for 18 years running.

Everything Is Included

Sit back and relax. Want a drink? We’ve got it! Cold beer, red & white wines, Champagne, and soda are available for sale on all our Maryland sailboat rides and are included on our evening charters.

Over 96 Years of Experience

Sail Selina’s top-notch skippers have a combined sailing history of 90+ years, and her friendly crew has a combined sailing history of 30+ years. We all love to sail and we love taking people for sailboat rides!

Spacious & Beautiful Boat

All our relaxing sailing boat charters are in a gorgeous setting. Sail Selina II was built as a gentleman’s yacht in the Gatsby era and is finished in freshly varnished mahogany and brightly polished bronze. Her spacious cockpit is the perfect setting for a Maryland sail on the ultimate charter boat in St Michaels, MD. Join us for a sailing charter boat tour and unwind with an authentic taste of the history of sail.

The Best Captains

Our St Michels boat tour captains are known for their storytelling skills and offer a boat trip balanced with some touring, some sailing, and some time to simply relax, unwind and kick back. When sailing on the Chesapeake in St Michaels, choose from a basic sailboat ride, or opt for a specialty outing like a local craft brew beer tasting cruise or a sunset champagne charter.

• Mediterranean
• South Pacific & Oceania
• South-East Asia
• Indian Ocean
• Northern Europe

Bareboat Monohulls

• Bareboat Motor Yachts

Bareboat Catamarans

• Crewed Yachts
• How our services work
• Multi-Database Searching
• Boat Charter Price Guidelines
• Free Charter Guide
• About Sail Connections
• Client Charter Reviews

Sail Chesapeake Bay

• Location Guide

Explore the USA's Largest Estuary and Discover America

Living in North America and looking for a bareboat charter destination close to home? Seeking to experience the natural beauty and the modern lifestyle of the USA? Wanting to vacation under sail but not bothered about snorkeling in clear blue tropical waters? Then take a look at Chesapeake Bay as a destination. 

So convenient for the locals and a fascinating place to visit from all over the world, Chesapeake Bay offers lovely summertime conditions for keen sailors and vacationing families. And all around this extensive sunken river valley are exciting places to explore, from secluded bays to modern cities with just about everything this part of USA has to offer.

It All Starts in Annapolis, America's Sailing Capital

Chesapeake Bay is a vast waterway, 200 miles long draining  64,000 square miles in six states via the more than 150 rivers that feed it. In the upper section of Chesapeake Bay you are in Maryland. The state's big city is Baltimore, while the capital is historic Annapolis, your likely starting point on a Chesapeake Bay sailing vacation. Annapolis is a lovely city that lies at the heart of the region's, some would say the nation's, sailing culture. It is also home of the National Sailing Hall of Fame and US Naval Academy - try to spare the time for a tour.

The Chesapeake's Upper Bay

Sailing out of Annapolis, turn the corner and you are immediately far from the bustle of the city. It doesn't take long to get a sense of the geography here – inlet after countless inlet formed as the sea level rose after the last ice age, beyond which wooded lowlands share the landscape with cultivated farm properties and a generous sprinkling of picturesque settlements.

Head south and a huge expanse of tidewater opens up. Bear northeast and sail under the monstrous dual-span Chesapeake Bay Bridge towards Baltimore, or on the eastern shore Rock Hall and the Chester River.

Rock Hall is a pleasant fishing village that offers an overnighting choice on a marina or at anchor in nearby Swan Creek. Just 15 nautical miles from base, getting to Rock Hall is an easy first day's sail. It's also a convenience stepping-off point for an upriver journey in either direction - to Baltimore's Inner Harbor or Chestertown, both with appeal in their own different ways. If you want to spend longer in the Bay's upper reaches, sail up to the Sassafras River and you can easily fill a week-long itinerary without going south of Annapolis. 

But to see more of this huge Bay with its 11,600 miles of shoreline, you need to head back under the big bridge. Immediately south of  Kent Island is Eastern Bay that brings you into the Wye River area. Here St Michaels is a popular stopover, a waterfront village with excellent marina facilities, shops and restaurants catering for the nautical crowd. St Michaels is also home to the Chesapeake Bay Maritime Museum. A short sail further south are Tilghman Island and Oxford, at the mouth of the Choptank River, setting for James A. Michener's great novel Chesapeake. 

This may well be all you have time to see on your Chesapeake Bay sailing vacation. However if you have longer, continue on south, exploring the eastern shore around Crisfield or crossing to Solomons Island if needing supplies or a marina berth.

The Middle Bay and South

Sail by the mouth of the Potomac River and across the state line into Virginia. Call at Smith or Tangier Island for an appreciation of the Chesapeake way of life and the wonderful natural environment in these parts. Most of the residents of Tangier Island make their living from crabbing, one of the Bay's big industries.

As you proceed south, you may wish to stop over at Deltaville for a berth and supplies, before heading across to the up-market coastal resort are of Cape Charles, with all its amenities for young and old. If time is still on your side, you can go as far as Portsmouth, rent a marina and take off by car to explore the area of Newport News, Norfolk and Virginia Beach.

As you sail back to Annapolis, there are numerous top spots you missed on your way out – Onancock,St Leonard's Creek on the Patuxent, and all those other inviting bays and rivers you observed on the way south. So leave plenty of time to stopover and make your return a leisurely sail.

Around these parts there is many a yachtsperson who will talk about sailing on the Chesapeake. How they've been doing it all their lives and still not been into half the bays and rivers. Head out and find your own special place, perhaps it'll be one that even the locals haven't  come across yet.

Browse our yachts for charter in Chesapeake Bay

Bareboat Motor Boats

Fully Crewed Yachts

The sail connections guarantee.

One contact - every option - advice you can trust.

• Matching any competitive offer
• Sourcing boats with discounts available
• Personalising our proposal just for you
• Qualifying the operator as well as the boat
• Advising without bias based on 25+ years of experience
• We do more than just book yachts!

We will match any discount website offer on charter boat price, and still provide our customary high level of service.

The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Enquire about a charter...

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.

Sailing Season is Here. Join Us for a Sail!

Sunset Sails

Welcome Aboard our two beautiful, wooden 74-foot schooners,  Woodwind  and  Woodwind II , for a true sailing experience in Annapolis, Maryland.

Sunset is a favorite time for a sail on the  Woodwinds . The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting off the sails as the sun descends near the horizon is an unforgettable sight.

Let our captain and crew make your trip an enjoyable and memorable experience.  Our bar is stocked with wine, beer and bubbly, including a nice selection of local, independent craft beers available for purchase.

History Mondays

A guided tour exploring the history of the Chesapeake area, and the sights you see while on a sail. Each week we will focus on a specific interesting topic with a guest speaker aboard. Early May – September.

Beer Tasting Tuesdays

Sample while you sail! Each month we feature a different brewery from the Chesapeake area. A representative from the brewery comes aboard and teaches you about beer. You will taste 3 samples of beer and then you can purchase full beers from the brews that you enjoyed the most. Early May through September. Schedule of Breweries.

Wednesday Night Races

Join the crew and race Woodwind vs. Woodwind II every Wednesday night from late April through late August.  There can be up to 100 other sailboats racing in the Wednesday Night Regatta sponsored by the Annapolis Yacht Club. Wednesday is the night to “Party Like A Sailor”.

Thursday, Friday, Saturday, and Sunday

There is no specific entertainment on these days of the week. There is so much to see as we sail by the United States Naval Academy and into the Chesapeake Bay. Let the crew serve you that favorite beverage as you relax watching the sunset over the city skyline.

1 thought on “Sunset Sails”

• Pingback: One Great Weekend: Annapolis, Maryland - Casual Travelist

Comments are closed.

• St. Michaels On The Bay
• The H.M. Krentz
• Join us for a sail
• Skipjack History

“ Relaxing, educational and unforgettable! ”

Enjoy a sailing tour on Chesapeake Bay waters aboard this rare skipjack.

The H.M. Krentz is an authentic working skipjack. One of the newer vessels to be built for the rigors of Maryland’s wintertime commercial oyster dredging fishery. Launched in 1955 in Harry Hogan, Va., by the Krentz Shipyard for Capt....

After choosing to pursue an education by experience, Capt. Ed participated in the pilot internship programs of Dynamy in Worcester, Mass., and worked with the Hurricane Island Outward Bound School and the Apprecticeshop in Maine. Then, sailing...

St. Michaels is the center of a unique and magical waterworld on Maryland’s fabled Eastern Shore, about halfway between the Susquehanna source and the Atlantic mouth of the Chesapeake Bay. This diminutive well-preserved vintage port,...

Chesapeake Bay Sailing Tours

Enjoy a relaxing, educational, and unforgettable sailing tour on Chesapeake Bay waters on the historic skipjack H.M. Krentz. We can arrange for catered picnics, cocktails and hor d’oeuvres, or you can bring your own food and beverages. Dress as comfortably and casually as you like.

Advance purchase recommended as t ours often sell out. 

**If you would like a private charter, please call (410) 745-6080 or email: [email protected]

Examples of Our Work

Designed by Elegant WordPress Themes | Powered by WordPress

Chesapeake Sail Club

Sail the chesapeake bay for the 2024 season, boad creek, deltaville, virginia.

Our home port, Broad Creek, at the mouth of the Rappahannock River, means great destinations on the river and bay are within an easy morning or afternoon sail.

Explore the numerous deep water creeks off the Rappahannock – drop your anchor or berth at the available facilities and explore local villages. Favorites include Urbanna, Topping and Irvington.

Set course for a secluded creek and enjoy the natural beauty and wildlife that only the Chesapeake Bay area can offer, favorites include the Corrotoman and Antipoison.

Sailing Chesapeake Bay from Broad Creek, heading either north or south there are numerous bays, rivers and waterfront towns to visit. Favorites include Fleet’s and Little Bays, Great Wicomoco River area and Mobjack Bay.

Sailing east, across the bay, to the eastern shore, you will find quaint and welcoming towns such as Onancock and Cape Charles.

Solomons, MD and Portsmouth/Norfolk, VA are within a few days of sailing from our Rappahannock home port, when your schedule allows.

What Members are Saying

My daughter and I had a great day sailing yesterday. The friends we took with us had a great day as well. Read more

The CSC Fleet – Our Sailing Yachts

With the start of the 2023 sailing season, club members can sail either Bianca , a Tartan 34 keel/centerboard sloop or Ula, a Freedom 32 – your choice each time you reserve sailing time. Both yachts are well equipped, comfortable cruisers.

The Chesapeake Bay is a spectacular North American cruising ground that was shaped by a big bang 35 million years ago when a comet or asteroid slammed into what is now the lower tip of the Delmarva Peninsula. That impact left a crater 55 miles wide that became a convenient depression for rivers to flow into as the glaciers of the last Ice Age melted some 10,000 years ago. The Algonquian word Chesepiooc, meaning “at a big river” became the source of the name for the estuary now called the Chesapeake.The Chesapeake Bay spans more than 64,000 square miles and is home to 150 major rivers and streams. A true boater’s playground, you will find everything you need. From live music and great tiki bars, to cruising with the kiddos, there’s no shortage of fantastic Chesapeake Bay marinas and fun activities here. Below please find a sample itinerary, complete with marina information, deals and discounts.

Cruising the Chesapeake Bay

From baltimore, md to cape charles, va.

The best of the Baltimore is located just steps off the docks at Harbor East Marina. Located in the heart of the city, the Harbor East area of Baltimore boasts 12 square blocks of fine dining restaurants, world-class hotels, hip lounges, quaint pubs, and the best of national and local shops. In addition to all that Harbor East has to offer, marina guests can walk to all the major attractions at the Inner Harbor, Fell’s Point and Little Italy including the National Aquarium and the Maryland Science Center. A quick cab ride will take sports fans to Oriole Park at Camden Yards and M&T Bank Stadium. From Harbor East Marina, guests are also just a short walk away from all of the major attractions at the Inner Harbor, Fell’s Point and Little Italy. Nestled in the center of it all, Harbor East is your gateway to discovering the best of Baltimore.

A walking tour of historic Annapolis, which is arrayed like spokes in a wheel from the Maryland State House, will delight architectural aficionados. Examples of Federal, Italianate, Georgian, Queen Anne and Greek Revival styles from the colonial period through the early 1900s abound. Good provisioning near the marina is hard to find. The locals’ favorite, Graul’s Market, with excellent produce, meat and fish is a mile and a half away. However, the marina has rental car and taxi services available to help stock up at Trader Joe’s, Whole Foods and Fresh Market. The Annapolis Yacht Basin has fuel and Annapolis Harbor Boat Yard is a full service maintenance yard that is conveniently located on Spa Creek near the historic district.

Rock Hall has everything a boater could wish for from first class service/maintenance facilities, restaurants, a grocery store, and fun events all accessible by bike, on foot, or by the great trolley system that connects all of the marinas. Rock Hall has many antiques and crafts stores including America's Past Antiques, Fishbone's Antiques, Rock Hall Gallery and the Artists of Rock Hall Gallery. You will also find gift stores, jewelry, clothing and accessories including Smilin Jake's Casual Apparel on Main Street. Don't miss Pirates and Wenches weekend aka Fantasy Weekend, which includes a decorated dinghy flotilla and kayak races, Caribbean beach party, treasure hunts, entertainment, contests and games for landlubbers and boaters alike. When looking for a place to grab a bite select from Bay Wolf Restaurant, Harbor Shack with live music on Saturday nights, and Waterman's Crabhouse.

For boaters, the focus of this Eastern Shore town is the Chesapeake Bay Maritime Museum with exhibits, restored vessels and hands-on boatbuilding workshops. It is where James Michener did his primary research for his best selling novel, “Chesapeake,” 40 years ago. The picturesque streets of St. Michaels are perfect to stroll along while looking for lunch or dinner. Topping off provisions is easily done within walking distance of the marina at Olivins, a gourmet grocery, or Acme supermarket. Fuel is available at St. Michaels Marina. Higgin’s Yacht Yard is the last full-service boatyard in existence in town.

Oxford’s main attraction is the town itself. It is one of the oldest towns in Maryland, officially founded in 1683. The charming, tree-lined village is a quiet antidote to the hustle and bustle of city life. The Oxford Market, a convenience store, is the only spot in town to buy any essentials for provisioning. If you need fresh fish and seafood, watch for the watermen when they bring their catch in early in the day. The marina is also a full-service boat yard, with gas and diesel available. Hinckley Yacht Services also has a full-service yard in town. Both Brewer and Hinckley provide quality work and craftsmanship.

Zahniser's Yachting Center is one of the most comprehensive marine facilities on the Chesapeake Bay; Located in the town center of Solomons Island, Maryland, Zahniser's is a full-service marina that blends the beauty of a pristine yacht club and the technical expertise of an award winning repair yard. It's the perfect starting point to enjoy the historic village of Solomons Island, either on foot or by bicycle. A destination not to miss - unwind, relax, and enjoy! The marina also has: WiFi, Courtesy Bicycles, a Recycling Center, a Sail Loft & Canvas Shop, Marine Surveyor, Sailing School & Yacht Charters. The marina can also haul vessels up to 70 tons.

Tangier Island is the home of working watermen who get up well before dawn to get their boats ready for crabbing and oystering. The island is most well known for its soft shell crab, for which it claims to be the world capital. With a total population of about 700, most who live there can trace their ancestry back to a handful of families. The small settlement is unique to the Chesapeake and wandering its lanes is the ideal way to pass the time after lunch or dinner at one of the two local restaurants. And, of course, order soft shell crab and crab cakes. Parks Marina is just across the harbor channel from the many crabbing shacks built on stilts along the shore. The marina is owned and operated by 85-year-old Milton Parks, and is a simple affair with fixed docks, pilings and a faded signboard. Milton gladly offers advice on how to dock in the strong current and, once your boat is tied up, he will spin many a story of the island’s inhabitants and history. Daley & Sons is the only grocery store on the island. There are no repair or fueling services for recreational boaters on Tangier Island, but in a pinch a waterman may be able to provide some assistance.

The Tides Inn Marina, 11 miles from Windmill Point on Carter’s Creek, is one of the most luxurious marinas on the Chesapeake Bay. Once docked on their private peninsula, you will have access to complimentary laundry, excellent shower and bath facilities, van and water taxi services, dining and lounges. The resort has a variety of dining options to choose from, all with their own unique style. Relax and recharge with therapeutic treatments at the Journey Spa, or play golf at the Golden Eagle Golf Course. There is always an array of outdoor activities available including tennis, kayaking, croquet, and complimentary bicycles.

Some cruisers who have visited this revived, historic railroad town on Virginia’s Eastern Shore say it’s one of the Mid-Atlantic’s best-kept secrets. Life is easy in this inviting bayside town, with bikes and golf carts sufficing for transportation and menus heavy with local seafood. With most of its structures built between 1885 and 1920, Cape Charles has one of the largest concentrations of restored late-Victorian and turn-of-the-century buildings on the East Coast. Many of these beautiful structures are now transformed into bed and breakfasts, galleries and specialty boutiques. The Gull Hammock Gourmet Market and Drizzles are two high-quality groceries for additional provisioning. They are adjacent to the historic district and conveniently located on your way back from the beach to your boat. At Cape Charles Yacht Center, yachts have full access to nearby Bay Creek Resort, featuring a Beach Club pool as well as two signature golf courses designed by Jack Nicklaus and Arnold Palmer.

Explore Other Regions

Best Sailing Destinations Chesapeake Bay

Last Updated by

Daniel Wade

May 9, 2023

‍ Key Takeaways

• The best sailing destinations in the Bay will vary based on your desired water activity
• A sailing trip in the Bay offers scenic views with great food and rich maritime culture
• Annapolis is the sailing capital of the world and gives Florida a run for its money
• Choosing the right boat is key to ensuring a safe travel and comfortable experience
• Summer months might be crowded so be sure to research the best opportunity for you

‍ Arguably one of the best sailing destinations, Chesapeake Bay, boasts beautiful scenery. But what are some of the best Chesapeake Bay sailing destinations?

The best sailing destinations in Chesapeake Bay are Annapolis and St. Michaels along with Norfolk. Other locations worth checking out are Solomons Island and Rock Hall as well as Smith Island. Keep in mind you need to travel the eastern shore of Maryland and Virginia to see all of these locations.

In my experience there is not much that compares to sailing in Chesapeake Bay. Annapolis is America’s sailing capital of the world for a good reason and is a great place to start.

Table of contents

‍ The Top 15 Best Sailing Destinations in Chesapeake Bay

Chesapeake Bay is quite popular for showcasing the natural beauty and a rich marine history. It has turned into a global sailing destination that offers plenty of exciting experiences for sailors of all kinds.

You can explore many top locations for a sailing adventure but it is recommended to start around Annapolis in Maryland since it is dubbed the sailing capital. Annapolis in general features picturesque villages and plenty of water locations to explore. Keep in mind that weather and navigational conditions vary across the bay.

Annapolis in Maryland is the renowned sailing capital for a good reason. It enchants sailors with the United States Naval Academy and has a rich marine history that features the famous Annapolis Boat Show.

Annapolis offers a lot of opportunities for sailors to dock and explore. This Chesapeake Bay harbor town allures with its scenic beauty. Below you can see other key attractions to this area.

• Abundant amenities to meet your needs
• Bustling harbor filled with marinas and boatyards
• Tons of restaurant possibilities

St. Michaels

St. Michaels has turned into a charming location due to its history and abundant sailing community. Be sure to bring a camera along this eastern shore town that showcases a beautiful harbor and Victorian homes. The town also is home to the Chesapeake Bay Maritime Museum where you can dedicate you time to check out the rich history and vibrant culture of the bay and its waterways.

Norfolk is a bustling harbor city on the Chesapeake Bay's southern coast that boasts a rich naval history as the site of the world's largest naval base. Sailors flock to this cultural hub that is renowned for various options below.

• Museums with rich history
• World-class restaurants

Numerous marinas throughout these cruising destinations grant convenient access to sheltered waters. This creates an opportunity for exciting city explorations.

Solomons Island

Solomons Island is another charming and historic town in southern Maryland that sits on the Patuxent River near the Chesapeake Bay. Its protected harbor attracts many sailors and its waterfront park and lighthouse offer scenic beauty.

There are an array of restaurants and shops to check out while staying at one of many marinas. Solomons Island proudly welcomes visitors to explore and unwind.

Rock Hall can be found on Chesapeake Bay's eastern shore where you will likely see an entire village of people fishing. It is loved by many for its natural elegance and wonderful waters.

Sailors that are drawn to crabbing or fishing experiences will want to stop here. The Chesapeake Bay Environmental Center is another additional location to check out since it offers educational programs to enlighten those about its history.

Deltaville offers fully equipped marinas and comprehensive maritime services that are complemented by a charming center for delightful strolls. Solomons' southbound boats often cross the Potomac River while navigating Virginia's Northern Neck rivers and creeks to reach Reedville or Deltaville in Virginia. Explore the vast waters of Great Wicomico or seek shelter in the protected haven of Mill Creek and capture the essence of the Southern Chesapeake.

Smith Island

Smith Island is a perfect sailing location. Those that are wanting to visit this Chesapeake Bay island must visit by boat since it is the only habitable island in Maryland.

There are three different villages in this location but they each offer clear waters and a calm sailing experience. This island is also famous for its Smith Island Cake.

Wye River has a combination of urban and marine areas that allow you to find peaceful surroundings. Wye Island and its 2,800-acre nature preserve are remarkable features that you cannot find anywhere else.

Tuckahoe State Park is one of these beautiful locations that you can check out after sailing. You also have a good chance to see amazing creatures in their natural habitats such as a bald eagle or blue heron. If you have a small enough boat you can explore more areas that are not accessible with larger sailboats.

Tangier Island

Tangier Island is in the Chesapeake Bay's south and is home to serious fishing opportunities. It is also home to the Tangier History Museum that will allow you to check out the island's culture.

There are plenty of boat tours that you could take to experience crabbing or fishing trips if you do not want to on your own boat. The area has secluded waters that make a great escape from reality.

Onancock is another Chesapeake Bay town considered a gem on the Virginia eastern shore. They too have a historic allure and that is coveted by a scenic harbor with a vibrant cultural heritage.

If you are wanting to experience a feeling like home then Onancock is a great opportunity. They have a tight knit community that engages in a lot of fishing and sailing. You can also see a beautiful sunset from many of the docks of your choosing.

Delaware Bay

Delaware City is located at the northern tip of Delaware Bay . This small community can be reached on foot from Delaware City Marina. This used to be a shallow salt marsh but the river becomes more wooded as you go upstream and offers a secure anchoring location with sufficient water depth and swinging space.

The western end of Cape May Canal marks the start of the harbor approach from Delaware Bay.

This expansive and exposed body of water stretches in a Southeast to Northwest direction. Before crossing Delaware Bay it is crucial to carefully check the weather forecast and can be an exhilarating journey under favorable conditions but caution is necessary in this particular area.

Kent Island

Kent Island is located in the heart of the Bay and shows off tons of rich marine history. It is surrounded by sheltered waters and it draws in sailors from all over the world.

You can find the Chesapeake Bay Bridge on this island which is a remarkable feat of architecture that connects the Bay's eastern and western shores. The harbor is a great place to hang out and to enjoy some of the best views for a perfect sunset.

Galesville is a delightful bay town on the west bank that once served as a steamship line hub connecting Annapolis and Baltimore. It was also home to numerous Chesapeake Bay watermen.

You will now see that the area is a sought-after destination for leisure boating with the West River Sailing Club and Hartge Yacht Harbor. This small peninsula offers a charming community park that features a 14-mile boardwalk along Riverside Drive and shows off scenic views of the West River.

Reedville is a charming fishing village at Chesapeake Bay's northern tip. It has a rich maritime history and thriving fishing industry to compliment the serene haven which lures sailing enthusiasts to its pristine waters.

When you explore the scenic harbor you can also check out these options below.

• Local boutiques
• Famous eateries
• Captivating heritage of the Chesapeake Bay's fishing traditions

The Patapsco River flows into Baltimore's Historic Inner Harbor and is an ideal starting point for sailing with numerous marinas. Explore the Harbor to admire landmarks like Federal Hill and Fort McHenry.

As the Patapsco opens up into the bay you can discover outdoor attractions such as North Point State Park and Fort Smallwood Park. Baltimore is a must-visit city for sailors that offers Henderson's Wharf Marina in Fells Point for a convenient anchorage near top pubs or taverns and music venues. There are abundant sailing and racing activities along with other limitless opportunities that might leave you feeling that you have only scratched the surface.

Key Benefits and Drawbacks of Sailing in Chesapeake Bay

Sailing in the Chesapeake Bay’s beautiful waters is a sight you have to see. The experience is definitely worth the trouble but some sailors could argue there are some drawbacks. Below are some of the common pros and cons to consider before sailing in the Bay.

• There are plenty of sailing locations to help you find a perfect experience. Each spot has its own appeal catered to sailing, fishing, or food.
• The Bay is famously known for its cuisine. You cannot miss out on the crab cakes and oysters but there are other options too if you do not like fresh seafood.
• There are plenty of secluded waters to explore. This offers sailors the perfect sailing environment no matter where they plan to go.
• You will find many marine historic sites and landmarks. This is a perfect opportunity for history buffs to brush up.
• You will be able to see various forms of wildlife like dolphins and bald eagles.
• There are a handful of expensive overnight dockage fees at certain Bay marinas that increase the cost of sailing in the area compared to other destinations.
• The Bay's sailing experience is impacted by environmental challenges like pollution and overfishing. This raises concerns about its quality but actions are being taken to currently help clean up the environment.
• Navigating certain areas of the Bay can be challenging. The summer typically has an increase of recreational boats and often creates crowded waters.
• The Bay endures demanding weather with strong winds and rough waters at certain times of the year. This is especially difficult in the winter months.
• Certain sailing spots within the Bay may offer limited access to essential amenities like grocery stores or repair facilities. You should also check in advance to be close to medical services in the event of any issues.

Ideal Boat Types to Sail in the Chesapeake Bay

Choosing the right boat is important for a safe and enjoyable sailing experience in Chesapeake Bay. Your ideal boat type will correlate on your needs and desires as well as the sailing conditions.

It is best if you conduct proper research based on your needs and the boat type you may already have. If you happen to be in the area you could also chat with local sailors to get their opinion.

Chesapeake Bay typically has these popular boat types:

• Daysailers are a perfect boating option designed for casual sailing. Those that are new to sailing generally gravitate to this boat type.
• Cruisers are an appealing sailboat type that offers a comfortable ride and speed. They also offer both relaxation and excitement. These are larger than daysailers but still easy to handle.
• Catamarans: This multihull boat provides stability and speed while also remaining comfortable. This allows for swift travel and tons of room on the boat for large groups.
• Center Console Boats are versatile options for anyone that wants to go fishing and cruising. They are usually small enough to go exploring Chesapeake Bay's inlets and coves. They also provide excellent visibility and handling no matter your experience level.

Why You Should Sail in the Chesapeake Bay

Choosing to sail in the Bay could lead to an unforgettable opportunity. There is more than a day’s worth of things to do in any location that you choose.

Appealing Scenery

There are not too many locations that you can sail to that have a balance between urban or city life and sailing. You will be able to see a lot more than people that do not have boats and the tours can only provide so much.

Calm Environment

Chesapeake Bay offers calm waters most of the time but checking the weather conditions is always best before making the trip. It does not matter if you are a first time boat owner or experienced sailor the weather will impact your performance. Thankfully the Bay has dependable weather.

Exciting Opportunities

Whether it is your first time sailing or you are visiting again the Bay offers endless opportunities. These could be fishing or crabbing and maybe even a new restaurant to try out. All of the locations have different historical aspects as well.

Best Memories

In combination of taking the opportunity to explore you will be making some of the best sailing memories. There is a reason why Annapolis is the center for sailing and the Bay is a perfect representation that offers the perfect package.

Related Articles

I've personally had thousands of questions about sailing and sailboats over the years. As I learn and experience sailing, and the community, I share the answers that work and make sense to me, here on Life of Sailing.

by this author

Destinations

Most Recent

Best Sailing Destinations In BC

June 28, 2023

Best Sailing Charter Destinations

June 27, 2023

Important Legal Info

Lifeofsailing.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon. This site also participates in other affiliate programs and is compensated for referring traffic and business to these companies.

Similar Posts

Can You Sail In Maine In October?

June 1, 2023

How To Sail From California To Australia

October 6, 2022

Best Sailing Destinations In Croatia

September 30, 2022

Popular Posts

Best Liveaboard Catamaran Sailboats

December 28, 2023

Can a Novice Sail Around the World?

Elizabeth O'Malley

June 15, 2022

4 Best Electric Outboard Motors

How Long Did It Take The Vikings To Sail To England?

10 Best Sailboat Brands (And Why)

December 20, 2023

7 Best Places To Liveaboard A Sailboat

Get the best sailing content.

Top Rated Posts

Lifeofsailing.com is a participant in the Amazon Services LLC Associates Program, an affiliate advertising program designed to provide a means for sites to earn advertising fees by advertising and linking to Amazon. This site also participates in other affiliate programs and is compensated for referring traffic and business to these companies. (866) 342-SAIL

© 2024 Life of Sailing Email: [email protected] Address: 11816 Inwood Rd #3024 Dallas, TX 75244 Disclaimer Privacy Policy

• MEMBER LOGIN

• Member Login
• Day Sailors
• Cruising Sailboats
• Take a tour of the Reservation System
• Run About Boats
• Cruising Power Boats
• Instruction
• Team Building
• 3 Hour Try Sail
• Maryland Boating Safety Course
• Member Resources

Cruising Sailboats for the Chesapeake Bay

There’s no better way to experience all the Chesapeake has to offer, cruising in a warm breeze with friends and family aboard the Club’s J/32’s, J/105’s, and Beneteau 33.  Being a member of the Club makes this dream a reality – and for far less money than ownership, charters or renting a sailboat.  Take a mini-vacation or an extended cruise with your family and friends using the Club’s cruising sailboats.  Your boat is ready and waiting for you!

Sail Club Level 2 Annual Membership Includes Unlimited Use of:

• (6) 26′ J/80’s
• (3) Harbor 20’s
• (3) 34′ J/105’s
• (3) J/32’s
• Beneteau 331
• Easy Online Boat Reservation System – Step Aboard and Go!
• No Maintenance, Repair or Dock Fees

See the Daysailors

Click here for checkout requirements    or  here for pricing,               .

The largest and at most famous estuary in the United States, Chesapeake Bay (or “the Chesapeake”) is truly an extraordinary place. Stretching across six states and the District of Columbia, the Bay watershed never ceases to amaze with its rich history, vital economic importance, and astounding beauty. And the wonders of sailing the Chesapeake Bay could fill a lifetime.

The history, natural beauty and wonderful ecosystem combine to present visitors with endless possibilities, and there’s a new adventure around every corner. However if you only have a limited amount of time to explore, it’s best to get an understanding of what there is on offer before your trip.

The following are a couple of tips for planning your sailing adventure on the bay.

How to Stay (Find Airbnbs & Hotels)

Here is an interactive map of hotels and airbnbs you can book in the Chesapeake area.

Be Realistic

If you try to see everything, it’s likely that you’ll miss a lot. Considering the scale of Chesapeake Bay , you will have to be realistic. It is not somewhere to speed around trying to encompass it all in one visit.

Do it right, and you will enjoy the experience so much more and thereafter, who knows, you may return to continue the adventure.

Remember the Definition of Cruising

To sail about for pleasure in an unhurried or unconcerned fashion, to move leisurely about an area. Let the Bay dictate your pace, stimulate your interest, suggest stops and places to see.

Be flexible in your approach, do plan, but don’t think that the plans cannot be altered once you arrive.

Summers are hot and humid, whereas Spring and Autumn are long, and much more comfortable. Even being on the Bay cannot always provide sufficient respite from the still humidity of the summer months, so be warned.

How to Travel

Cruising can take two forms. You can charter a vessel either bareboat or crewed .

Bareboat – You take charge of the boat yourself and provide the crew, and if you are a competent sailor, then this may heighten the excitement, but it is also less of a vacation and more of an adventure. Don’t forget also the issue of stopovers, are you mooring, docking, or anchoring the boat!

Crewed – the cruiser is manned with a captain and crew, and you can sit back and enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties.

Itinerary Suggestions

There is simply so much, in a sense too much, to see, so it may be a good starting point to pick a more defined area of the Bay and concentrate on that.

Though you’re looking for variety then sailing the Chesapeake area is a natural cruising route for discovery, made for simply hopscotching from one shore to the next, with things to see, visit, experience, taste and indulge all of your senses at once.

Commonly visited areas include Havre de Grace via the Chesapeake & Delaware Canal built in 1829. Many people choose to visit the inner harbour of Baltimore travelling along the Sassafras River with its steep banks and from there to Rock Hall, a sailors town famed for its seafood; travel from St Michaels to Annapolis, known as the sailing capital of the World ; onward to Oxford on the Trent Avon, a sleepy, quaint and picturesque town, or finally on to Washington DC should the mood take you.

You will find yourself with so many options and avenues of adventure, so many that a sense of spontaneity should be a prerequisite. Whilst you slowly absorb the sights, sounds and scenery as you are cruising, you can smile to yourself and be proud that you chose to sail the Chesapeake Bay.

YOU NEED THESE FOR SAILING: CLICK PHOTO ↓

INSPIRED? PIN THESE TO YOUR TRAVEL PINTEREST BOARDS↓

If You Liked This Post You May Also Like:

Best Sailing Destinations in the British Virgin Islands

Want to Do More than Swim? Visit these Unexpected Aussie Beaches!

Tasha Hacker on Sailing, Ocean Racing and Traveling by Sea.

Megan is an Australian Journalist and award-winning travel writer who has been blogging since 2007. Her husband Mike is the American naturalist and wildlife photographer behind  Waking Up Wild ; a website dedicated to opening your eyes to the wild & natural world.

Committed to bringing you the best in adventure travel from all around the globe, there is no mountain too high, and no fete too extreme! They haven’t been everywhere, but it’s on their list.

Follow their journey on Facebook , Twitter ,  YouTube , Pinterest and Instagram .

20 Comments

Great post, loved the pics! I’ll definitely try to go to Chesapeake!, I’m the kind of person who don’t want to miss anything but I’ll follow your advice “If you try to see everything, it’s likely that you’ll miss a lot.” and as you said, maybe I could return a second time and try to see everything. Thanks for the info! Pilar http://www.thelifestylehunter.com

Thanks Pilar! So glad you enjoyed the post :) Yes, definitely recommend to pick a more defined area of the Bay and concentrate on that if it’s your first time visiting – there really is just so much to see and do that it’s better to do a little and enjoy it fully than try to slam out a lot and enjoy it half as much.

Hope you have an amazing time!

At university I had a friend who was always talking about the wonders of Chesapeake Bay and she made it sound like something I really should do. Many years later, I still haven’t, but your post has reminded me how wonderful it sounded.

So glad we could remind you Sarah! Yes, highly recommend a trip – it’s a beautiful bay with so much to see and do :)

Great tips! You’re so right about the weather. I live in DC and the summers are unbearable. Sailing in the fall is the best time. Annapolis is my favorite place on the bay.

Thanks Jessica :) Awesome to hear you’re already familiar with sailing on the Bay :)

I will go for the bareboat one where you have total control. Loved the suggestions and nice pics.

Awesome Gokul! Glad to hear we’ve inspired you to take a trip :) Let us know how you enjoy the Chesapeake

Really good tips. Would love to do this. I would love to lay out and let someone man the boat.

Thanks Holly – yes, jumping on a crewed boat is great if you’re looking to enjoy the trip and all the sights without having to worry about any of the mundane logistics and duties :)

Happy travels!

This is my home! I was so excited to see my beautiful corner of the world featured!

What an incredible place to grow up! Not bad having Chesapeake Bay as your backyard :) Awesome!

Hey Megan, I once got invited on a boat but the trip never ended up going through as the boat needed tons of work and couldn’t get out of the port. This sounds amazing. I’d prefer warm waters in the Caribbean but I imagine seeing this side of the US would be gorgeous as well. Thanks for the post. Cheers, Jack

Hi Jack, thanks for your comment :) Sorry to hear your boat didn’t end up going out on Chesapeake – totally agree that the Caribbean is an incredible spot for sailing too. Very different experience to the Bay but they both make for great sailing :)

Dear Sir, May 22nd, 2018 I have a 27 ft Bayliner sailboat and I would like to sail from Norfolk to Annapolis and back. I have never done this before but it is something that I really want to try. My daughter lives near Annapolis and is close to the water (West River). I feel that I need some bay sailing but I do know how to sail on lakes (Smith Mountain Lake in VA). I am retired and am a good swimmer. I have no idea as to where one would stop for the night and how long it would take and how safe it is to do this. These are my questions and I would like to talk to your group about lessons and feasibility.

Thanks in advance for your time.

Tim Kute 336-413-6126 [email protected]

Hi Tim, thanks for reaching out. We’re a couple who run a personal blog with tips from our adventures, so unfortunately can’t advise you on things like organizing lessons or your level of experience. I would pose your questions to the team at Annapolis Bay Charters who may be able to offer you more insight. Hope they can help :)

http://www.annapolisbaycharters.net

Hi, Sailing is a life fun for those who live for sail like me.I really like the Sailing tips you share with those who live for sail. its help the new sailors in sailing and boost the moral of the experienced sailors. i appreciate your efforts. One thing i like to add is that don’t forget to protect your hands during sailing with premium quality sailing Gloves.

Glad to hear from a fellow sailor! Great tip on remembering to include gloves in your kit :)

Thanks for this. We are thinking of sailing down from Boston to Chesapeake via canal. We have 6-week sabbatical so plenty of time. We would like to avoid the worst of the summer heat/humidity, what would be best time to go in your opinion?

Also, I’ve heard that there are a lot of shallow spots in the bay, we draw 6′, any specific areas to avoid?

Thanks, Sea Fever

Hi David :)

Re best time to head out, I would say anytime from April until June, after that and once it hits July it gets really humid so I would avoid at all costs.

For good anchorage spots and plannig out your trip, check out the Gunkholers guide to the Chesapeake, it’s a cruise planner with suggested itineraries but also has charts and waypoints for anchorages and key locations. It’s always very up to date too :)

Have an amazing trip!

Post a Reply Cancel reply

Your email address will not be published. Required fields are marked *

Save my name, email, and website in this browser for the next time I comment.

Search This Site

I am Megan Jerrard, professional travel blogger/journalist with a focus on adventure, discovery, immersion and inspiring you to explore!

Recent Posts

• 8 Essential Financial Tips for Solo Female Travelers
• How Travel Improves Mental Health for Solo Adventurers
• How Adventure Travel Strengthens Deep Bonds Between Companions
• 3 Tips for Solo Hiking in 2024
• Camino Portugues: Highlights You’ll Find From Porto

Popular posts

• International Love: Maintaining a Long Distance Relationship
• Illegal Ink – 11 Countries Where Showing Your Tattoos Could Get You Kicked Out!
• 7 Things To Know Before Travelling by Overnight Train in Vietnam
• A Travelers Guide to Tap Water: Countries Where The Drinking Water is Unsafe
• Countries That Don’t Celebrate Christmas

Local News | Sailing through history: Ocean View shrine…

Share this:.

• Click to share on Facebook (Opens in new window)
• Click to share on X (Opens in new window)

e-Pilot Evening Edition

• Latest Headlines
• OBX and North Carolina
• Virginia Beach

Breaking News

Local news | virginia primary election live results, subscriber only, local news | sailing through history: ocean view shrine marks susan constant’s arrival in virginia.

The current ship replica replaced an earlier iteration created for the 350th commemoration at Jamestown Festival Park in 1957. The new ship, commissioned in April 1991, has served as the flagship for Virginia’s official fleet of 17th-century vessels for 33 years. Over 19 million visitors have crossed her planked decks to experience a bit of maritime life.

For more than three decades, Capt. Eric Speth, director of maritime operations for the Jamestown-Yorktown Foundation, has commanded the vessel and implemented its water-borne ambassadorship.

“I love what I do, and I feel so fortunate to be able to work with the people I work with, the volunteers and the staff here at Jamestown Settlement,” Speth said.

Today, the bayside park in Ocean View is called Sarah Constant Beach Park in tribute to the flagship Susan Constant, the largest of three chartered English ships (Susan Constant, Godspeed and Discovery) that brought the colonists who established the first permanent English settlement in the New World at Jamestown.

On the grounds of the beach park near a cluster of live oak trees, a Virginia historical highway marker memorializes the ships and colonists who founded the English settlement on Jamestown Island in the early 17th century. Between the parking lot and the waters of Chesapeake Bay, on sandy ground, stands a shrine that bears an illustration of the Flagship Sarah Constant and a small plaque clarifying the tribute.

An engraved wooden sign on West Ocean View Avenue designates the site as Sarah Constant Beach Park, City of Norfolk. Parking is available. Restroom facilities are located in the park. A cluster of live oak trees provides shade from the sun. The sandy beach offers an impressive view of the Chesapeake Bay and the Ocean View Fishing Pier.

While the signage at the park seems to indicate a disparity, the names Sarah Constant and Susan Constant are references to the same historic vessel that accompanied the Godspeed and the pinnace Discovery in 1607.

The disparity in names probably had its origins in an error created by Anglican cleric Samuel Purchas, an Elizabethan-era travel writer who dubbed the vessel Sarah Constant instead of Susan Constant.

While the city of Norfolk and the Daughters of the American Revolution, Sarah Constant Chapter cling to the appellation Sarah Constant, Virginia prefers the name Susan Constant. The state historical highway marker on the Ocean View park site refers to the ship as the Susan Constant.

Regardless of what one chooses to call the replica vessel, we know that the original ship was a mid-size merchant vessel. It was three-masted, barque rigged. It carried square sails on the foremast, main mast, and spritsail under the bowsprit and a fore and aft rigged sail on the mizzen mast at the aft end of the vessel.

At Jamestown Settlement the ship is known as the Susan Constant. In Speth’s mind, there is no question about the ship’s identity.

“Susan Constant,” Speth said. “I think we see that in the historic record and also that is the official spelling in Virginia. Our fleet of ships here at Jamestown Settlement Museum are the Susan Constant, Godspeed and Discovery. They are the official fleet of the commonwealth of Virginia and Susan Constant is the flagship of the fleet.”

A visit to Sarah Constant Beach Park in Ocean View is worth the time to view the shrine and historical marker. It also offers a beautiful beach view of the Chesapeake Bay.

A timely visit to this bayside park in Ocean View in the next few days might even provide a sighting of the Susan Constant replica as the craft passes through the Chesapeake Bay and heads to New England for restoration. The ship is expected to set sail as early as this weekend.

More in Local News

Crime and Public Safety | Indiana man arrested on Outer Banks for firing gun in camper ‘to incite fear’

Local News | Real or fake? Orca photos off Outer Banks spark questions.

Weather | Today’s weather: Warm day with a mix of sun and clouds

Crime and Public Safety | Woman shattered windows, fired gun before Newport News police officer shot and killed her

Trending nationally.

• NYC to see dangerous heat wave this week: How hot will it get? How long will it last?
• Puerto Rican musician Don Omar battling cancer at Orlando hospital
• Why is the NFL being sued over its ‘Sunday Ticket’ package?
• How Disneyland passholders can get their share of $9.5 million Magic Key settlement
• John Oliver Bear Cake craze rakes in bonanza for food pantry

• Bahasa Indonesia
• Eastern Europe
• Moscow Oblast

Elektrostal

Elektrostal Localisation : Country Russia , Oblast Moscow Oblast . Available Information : Geographical coordinates , Population, Altitude, Area, Weather and Hotel . Nearby cities and villages : Noginsk , Pavlovsky Posad and Staraya Kupavna .

Information

Find all the information of Elektrostal or click on the section of your choice in the left menu.

• Update data

Elektrostal Demography

Information on the people and the population of Elektrostal.

Elektrostal Geography

Geographic Information regarding City of Elektrostal .

Elektrostal Distance

Distance (in kilometers) between Elektrostal and the biggest cities of Russia.

Elektrostal Map

Locate simply the city of Elektrostal through the card, map and satellite image of the city.

Elektrostal Nearby cities and villages

Elektrostal Weather

Weather forecast for the next coming days and current time of Elektrostal.

Elektrostal Sunrise and sunset

Find below the times of sunrise and sunset calculated 7 days to Elektrostal.

Elektrostal Hotel

Our team has selected for you a list of hotel in Elektrostal classified by value for money. Book your hotel room at the best price.

Elektrostal Nearby

Below is a list of activities and point of interest in Elektrostal and its surroundings.

Elektrostal Page

• Information /Russian-Federation--Moscow-Oblast--Elektrostal#info
• Demography /Russian-Federation--Moscow-Oblast--Elektrostal#demo
• Geography /Russian-Federation--Moscow-Oblast--Elektrostal#geo
• Distance /Russian-Federation--Moscow-Oblast--Elektrostal#dist1
• Map /Russian-Federation--Moscow-Oblast--Elektrostal#map
• Nearby cities and villages /Russian-Federation--Moscow-Oblast--Elektrostal#dist2
• Weather /Russian-Federation--Moscow-Oblast--Elektrostal#weather
• Sunrise and sunset /Russian-Federation--Moscow-Oblast--Elektrostal#sun
• Hotel /Russian-Federation--Moscow-Oblast--Elektrostal#hotel
• Nearby /Russian-Federation--Moscow-Oblast--Elektrostal#around
• Page /Russian-Federation--Moscow-Oblast--Elektrostal#page
• Terms of Use
• Copyright © 2024 DB-City - All rights reserved
• Change Ad Consent Do not sell my data

• Election 2024
• Entertainment
• Newsletters
• Photography
• Personal Finance
• AP Investigations
• AP Buyline Personal Finance
• AP Buyline Shopping
• Press Releases
• Israel-Hamas War
• Russia-Ukraine War
• Global elections
• Asia Pacific
• Latin America
• Middle East
• Election Results
• Delegate Tracker
• AP & Elections
• Auto Racing
• 2024 Paris Olympic Games
• Movie reviews
• Book reviews
• Personal finance
• Financial Markets
• Business Highlights
• Financial wellness
• Artificial Intelligence
• Social Media

Melvin, Findlay and Burnham head the National Sailing Hall of Fame’s Class of 2024

• Copy Link copied

NEWPORT, Rhode Island (AP) — Pete Melvin, who helped design breakthrough boats for the America’s Cup as well as the Nacra 17 used in the Olympics, and Conn Findlay, who won Olympic medals in sailing and rowing, head the list of 12 inductees in the National Sailing Hall of Fame’s Class of 2024.

As part of the firm M&M, Melvin helped design the giant trimaran that tech tycoon Larry Ellison’s BMW Oracle Racing used to win the 2010 America’s Cup in a one-off regatta against Alinghi of Switzerland’s giant catamaran. M&M also drafted the design rules for the 72-foot catamarans used in the 2013 America’s Cup, which ushered in foiling in sailing’s marquee regatta.

M&M designed the Nacra 17 catamaran that debuted in the 2016 Olympics. For the 2021 Olympics in Tokyo, the Nacra 17 added foils. Melvin sailed in the 1988 Olympics and has won numerous national and world titles.

Findlay won a total of four Olympic medals, including a bronze medal with Dennis Conner in the Tempest class in 1976. In rowing, he won two golds and one bronze in coxed pairs. He sailed in the America’s Cup three times, including with winning skipper Ted Turner aboard Courageous in 1977.

Also entering the hall is Kevin Burnham, who won a silver medal in the 470 class in the 1992 Olympics with Morgan Reeser and then won gold with Paul Foerster in 2004.

In one of the most memorable races in Olympic history, Foerster and Burnham aggressively match-raced the British boat to the back of the fleet and stayed ahead the entire race to win the gold medal. At the finish line, Burnham, then 47, waved to race officials, let out a whoop and then did a backflip into the Saronic Gulf off Athens, barefoot and still wearing his sunglasses. Burnham died in 2020.

The induction will be Oct. 4-5 at the Chicago Yacht Club.

Among the other inductees are Jan C. O’Malley, a three-time US Sailing Yachtswoman of the Year and the first winner of the IYRU Women’s World Sailing Championship; Charles Ulmer, a national champion and race winner throughout the 1970s and 80s; and Richard Tillman, the 1965 Sailor of the Year who held national, North American and world titles in the Snipe, Finn, Laser, Sunfish and Windsurfing classes.

Also going into the hall are Franklin Wood; Allegra Mertz; brothers Eric Hall and Ben Hall; Gary Mull; and Carl Alberg.

Wind & weather forecast Elektrostal

• Superforecast

Daily forecast

Wednesday, jun 19, thursday, jun 20, friday, jun 21, saturday, jun 22, sunday, jun 23, monday, jun 24, tuesday, jun 25, wednesday, jun 26, thursday, jun 27, friday, jun 28, nearby spots (within 25 km).

• Fryazevo 6km
• Noginsk 9km
• Imeni Vorovskogo 10km
• Rakhmanovo 11km
• Pavlovsky Posad 12km
• Obukhovo 13km
• Pavlovsky Posad 14km Weather station Live measurements

Look at our wind map to find more spots among our 160,000 spots.

Elektrostal popularity

Most popular spots in russia.

Have a look at the top kitesurfing, windsurfing, sailing, surfing or fishing spots in Russia

Additional information

Check the wind forecast for Elektrostal when you search for the best travel destinations for your kiteboarding, windsurfing or sailing vacations in Russia. Or use our wind forecast to find the wind speed today in Elektrostal or to have a look at the wind direction tomorrow at Elektrostal.

Severe Weather Warnings