annapolis sailboat

Sailing Season is Here. Join Us for a Sail!

Welcome Aboard!

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

Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!

Make your sailing experience a memorable one! Sail away with us!

You are using an outdated browser. Please upgrade your browser to improve your experience.

• Annapolis: 410.263.8234
• Cape Cod: 508.524.9121
• Booking Information
• Buy Cape Cod Tickets Now

A Grand Experience for All

Custom built for sailing, comfort and fun. Our cruising grounds are some of the most beautiful and historic in the country

Corporate Events

Special occasions, adventure & entertainment.

Custom built for sailing, comfort and fun, the Liberte is a grand experience for all. Our cruising grounds are some of the most beautiful and historic in the country. The captain and crew are dedicated to your safety, comfort and enjoyment.

USCG certified for 49 passengers. Music. Full bar. Every Sail is Unique.

One Great boat, two great locations

About the boat.

The schooner, Liberté, is based on Spa Creek in Annapolis, Maryland. During the summer months, she’s docked at the Patriot Party Boats pier in Falmouth harbor in Cape Cod, Massachusetts. Captain Chris and Jane had this vessel built just for them.

The original hull design by Dudley Dix is a Hout Bay 70, a two-masted gaff-rigged schooner intended as a heavy but fast offshore cruiser. Many alterations were made to the design, including adding a spoon bow, scaling down the lines to meet U.S. Coast Guard parameters, redesigning the deck layout and adjusting the rig to a three-masted staysail design.

Get In Touch Now

• © 2024 The Liberté
• All Rights Reserved
• Website Design & Marketing provided by Adventure Web Interactive

Subscribe To Our Weekly News & Deals

• Boats for Sale
• Sell Your Boat

BOATS FOR SALE

SELL YOUR BOAT

Your trusted full-service boat buying experts.

• Since our establishment in 1953 by Lawrence Hartge in Annapolis, MD, we have been proudly serving boating enthusiasts on the stunning Chesapeake Bay with exceptional service and unparalleled expertise.
• Lawrence Hartge, a visionary and passionate boater, laid the foundation of our company with a simple yet powerful mission: to offer a full-service boat buying experience that surpasses expectations.
• His dedication to the craft and his love for the Chesapeake Bay set the tone for our company's values, which we continue to uphold to this day.
• Over the years, we have become synonymous with excellence in the Mid-Atlantic region.
• Whether you're a seasoned sailor or a first-time buyer, we understand the unique needs and preferences of our customers, and we strive to match them with the perfect vessel.
• Our extensive selection of boats caters to all tastes and budgets. From sleek powerboats to classic sailboats, we offer a diverse range of options that will suit any boating enthusiast.
• Whether you're looking to buy, sell, or simply enhance your boating experience, we are here to make your dreams a reality.
• Come visit us and tour our boats at Pier 7 Marina in Edgewater, MD.

Sign Up For Our Weekly News & Deals

48 S River Rd S, Edgewater, MD 21037

(410) 267-8181

[email protected]

© 2023 All Rights Reserved  

• Find A School
• Certifications
• North U Sail Trim
• Inside Sailing with Peter Isler
• Docking Made Easy
• Study Quizzes
• Bite-sized Lessons
• Fun Quizzes
• Sailing Challenge

How to Make the Most of This Year’s Annapolis Sailboat Show

By: Zeke Quezada, ASA American Sailing , Boat Shows

A shiny new sailboat will make your heart race, your palms sweat, and trigger the butterflies in your stomach. Stand on the boat of your dreams, and you’ll feel a powerful and intense feeling of affection, attraction, and emotional connection.  Amid the lively Annapolis Sailboat Show, I absorb the inspiration and ponder my own sailing journey. Around, dreams blossom—a vibrant tapestry of aspirations. Witnessing the joy of a boat purchase nearby, I sense the essence of possibility. Dreams meet reality on the dock in Annapolis as old goals are achieved, and new goals are set.

Up and down the rows of the show, you see bright flags and shiny vessels capturing your every glance. At last count, over 400 vendors attend the boat show, exposing you to the newest and coolest objects of desire. How great would it be to outfit your boat with all-new electronics? Imagine new sails to replace those tired but storied rags on your sloop. Can you ever have enough jackets or gloves or winch handles?

The Annapolis Sailboat Show is a spectacle for sailors and lovers of all things sailing. Everywhere you turn, conversations fill the air about vacations in the Med or anchors that can hold fast in all conditions or the dream to sail the world. 

The Annapolis Sailboat Show allows us to dream while seeking inspiration and motivation and engaging in some infatuation.

Why Should You Go to the Annapolis Sailboat Show?

Heading to Annapolis for this popular event is a sailor’s hall pass to enter a world of maritime innovation and inspiration. Nestled amongst a vibrant gathering of industry experts and enthusiasts, expose yourself to the unveiling of the latest vessels, cutting-edge technologies, and nautical gear. From connecting with like-minded individuals to exploring diverse sailing options, the sailboat show offers a firsthand experience of sailing’s finest offerings. Engaging seminars, networking opportunities, and a palpable atmosphere of a sailor’s passion further enrich the experience. Whether seeking a new vessel or simply immersing oneself in the sailing lifestyle, a boat show equips sailors with insights, knowledge, and connections that amplify their sailing journey.

10 Reasons to Attend the Annapolis Sailboat Show

• Dare to Dream about a New Boat: The show features a diverse and wide selection of sailboats, from small day-sailers to luxurious yachts. Whether you’re a novice sailor or an experienced boater, you’ll have the opportunity to explore and compare different types of sailboats, from various manufacturers and in different sizes.
• Hands-On Experience: Unlike traditional boat shows, the Annapolis Sailboat Show often allows attendees to step aboard many of the boats on display. This provides you with a chance to get a real feel for the boats, check out their features and layouts, and even discuss their design and performance with knowledgeable exhibitors.
• Educational seminars to open up your horizons: The Annapolis Sailboat Show typically hosts a series of seminars, workshops, and demonstrations on a wide range of topics related to sailing, boating safety, navigation, maintenance, and more. These educational opportunities can enhance your understanding of sailing and help you develop your skills. Maybe you will find that sailing destination you never knew was possible actually is well within your ability!
• Meet the rockstars and influencers of the sailing world: The show brings together boat manufacturers, dealers, and industry experts. This is a great opportunity to engage in conversations with professionals who can provide insights into the latest trends, technologies, and innovations in the sailing world.
• Networking with other sailors: If you’re passionate about sailing, this event provides an excellent platform to connect with fellow sailing enthusiasts. You can share experiences, exchange tips, and potentially make new friends who share your interest in boating.
• Exclusive deals that turn dreams into reality: Boat shows often offer special pricing, discounts, and promotions that may not be available at other times of the year. If you’re in the market for a sailboat or sailing-related equipment, the show could be an opportunity to find some great deals.
• Discover the latest tech and products: In addition to sailboats, the show usually features various exhibitors showcasing the latest sailing gear, equipment, accessories, and technologies. You can discover new products that could enhance your sailing experience.
• Scenic Location: Annapolis, known as the “Sailing Capital of the United States,” provides a picturesque backdrop for the event. The historic maritime town offers a charming atmosphere with waterfront views, local restaurants, and cultural attractions.
• Fun and Entertainment: Beyond the boats and equipment, the Annapolis Sailboat Show often includes entertainment, live music, and social events that make the experience enjoyable for attendees of all ages. Find a karaoke bar and sing with sailors until the early morning hours!
• Inspiration: Even if you’re not in the market to buy a boat, attending the show can be a source of inspiration for future sailing adventures. It’s a chance to immerse yourself in the sailing world and dream about future voyages.

In summary, the Annapolis Sailboat Show offers a unique opportunity to immerse yourself in the world of sailing, explore a wide range of sailboats, learn from experts, and connect with fellow sailing enthusiasts. Whether you’re a seasoned sailor or just curious about the boating lifestyle, the show can provide a memorable and enriching experience.

Learn from Experts in These LIVE American Sailing Seminars 

American Sailing is hosting a series of live seminars during the Annapolis Sailboat Show that are sure to help you achieve your sailing goals.

SECRETS OF SUCCESSFUL CRUISING

HOSTED BY GIO & JULIE CAPELLI

Pelagic Blue Cruising Services, Owners

✓ Expert Sailors and Instructors

✓ Diverse Expertise

ANNAPOLIS, MD

FRI, OCT 11, 2024

For cruisers and aspiring cruisers intrigued by the secrets to setting sail with confidence and joy, this live seminar will address and navigate the challenges at sea, covering coastal and offshore passages, self-sufficiency in boat maintenance, and relationship dynamics with your crewmate(s).

HOW TO SAIL AROUND THE WORLD

HOSTED BY JAMIE & BEHAN GIFFORD

Sailing Totem

✓ Seasoned Circumnavigators

✓ Cruising Experts and Authors

Join experienced circumnavigators and cruising coaches Jamie and Behan Gifford for a comprehensive, information-packed session on How To Sail Around The World. During this live seminar, Jamie and Behan will be sharing tips, tricks, and shortcuts for launching a safe and successful circumnavigation.

CRUISE WITH CONFIDENCE

HOSTED BY LISA & ANDY BATCHELOR

Kinetic Sailing, Owners Sail Solomons ASA School, Founders

✓ Award-Winning Sailing Instructors and Authors

✓ Distinguished Cruising and Passagemaking Background

SAT, OCT 12, 2024

Discover the key to successful extended cruising. Whether you’re just dreaming of setting sail or already living the liveaboard life, Lisa and Andy Batchelor, ASA Master Instructors, will offer invaluable insights and practical advice during this live seminar. From boat equipage to sail trim and docking, learn how to prepare yourself to cruise with confidence and clarity.

GUIDE TO BOAT BUYING

HOSTED BY JOHN NEAL

Log Of The Mahina, Author

✓ Expert Sailing Trainer and Author

✓ Extensive Offshore Experience

During this live seminar, learn what the current state of the boat market is, how to navigate the purchase process, and the experience needed to gain insurance in the ever-changing times. Hear inside tips from industry experts on how to find the right boat for you as they walk us through the procedures of selecting a sailing yacht that is ideal for cruising while analyzing current market examples of prices and trends.

HOW TO TROUBLESHOOT & FIX COMMON DIESEL ENGINE PROBLEMS

HOSTED BY NIGEL CALDER

Marine Diesel Engines, Author

✓ Innovative Marine Engineer

✓ Prolific Author and ABYC Veteran

SUN, OCT 13, 2024

Unlock the secrets of diesel engine troubleshooting in this live seminar with Nigel Calder, author of best-selling book Marine Diesel Engines. Gain practical insights into diagnosing and fixing common issues like overheating, power loss, and more. Perfect for current or future boat owners seeking to enhance their understanding of diesel engines and resolve problems efficiently.

PRACTICAL ELECTRICAL SYSTEMS TROUBLESHOOTING FOR BOATERS

Dive into common boat electrical system issues with Nigel Calder as he outlines simple step-by-step troubleshooting techniques that can be safely conducted by any boat owner, including using a multimeter. Live seminar attendees will learn how to head off common battery and systems failures and rapidly identify the majority of electrical problems seen on boats. The goal of this seminar is to raise your confidence levels of boat owners, given today’s increasingly electrically-loaded and complicated boats.

Make Plans To Attend The Annapolis Sailboat Show

You might find yourself admiring the couple embarking on their journey with a new Beneteau, sensing the allure of their adventure. And you’ll share a knowing smile with the young enthusiast donning a fresh Helly Hansen jacket, recognizing the spirit of exploration and discovery they embrace. You will leave the boat show with a newfound motivation to escape into the fantasy of sailing. Spend enough time with fellow sailors, and their energy is intoxicating.

If you ever needed the gentle nudge to do more with your love for sailing and the sailing lifestyle, you can bet that a couple of days in Annapolis will push you in the right direction. 

Related Posts:

• Learn To Sail
• Mobile Apps
• Online Courses
• Upcoming Courses
• Sailor Resources
• ASA Log Book
• Bite Sized Lessons
• Knots Made Easy
• Catamaran Challenge
• Sailing Vacations
• Sailing Cruises
• Charter Resources
• International Proficiency Certificate
• Find A Charter
• All Articles
• Sailing Tips
• Sailing Terms
• Destinations
• Environmental
• Initiatives
• Instructor Resources
• Become An Instructor
• Become An ASA School
• Member / Instructor Login
• Affiliate Login

Servicing Annapolis Maryland and the greater Chesapeake Bay waterfront area.

• Create Account

Signed in as:

[email protected]

Bringing performance and recreational sailboats, equipment, apparel, and repairs to Annapolis and the greater Chesapeake Bay!

It's time to gear up for spring and summer sailing!!!

About annapolis sail works, our mission.

As a veteran-owned and operated small business, we strive to serve the local sailors and performance water sports athletes of the Chesapeake Bay with the best boats, equipment, repairs, and expertise to make competitive sailing and other watersports accessible and sustainable for all.

Veteran-owned Small Business

 A veteran-owned and operated company, Jake Crespin and Jeff Daigle established Annapolis Sail Works in 2023 to serve the Chesapeake Bay waterfront community with high-quality sailboats, equipment, repair services, and expertise. Jake and Jeff are both avid lifelong sailors with extensive sailing and marine industry backgrounds and a passion for boats, performance, and recreational sailing. Jeff is a retired career Coast Guard Helicopter Pilot and a Texas Maritime Academy graduate, where he was captain of the varsity sailing team. Jake is a career Marine Corps Infantry Officer and graduate of the U.S. Merchant Marine Academy, where he sailed on the Kings Point varsity dinghy and offshore teams. Both owners race various classes of dinghies, keelboats, and offshore boats. They founded Annapolis Sail Works to make high-performance and recreational sailing on the Chesapeake Bay more accessible and sustainable by bringing a full-service dinghy shop back to Annapolis, MD. 

[email protected]

Drop us a line!

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Copyright © 2024 Annapolis Sail Works - All Rights Reserved.

This website uses cookies.

We use cookies to analyze website traffic and optimize your website experience. By accepting our use of cookies, your data will be aggregated with all other user data.

Classic Sail Charters

Private sailing charters in maryland, choose your location, annapolis, md.

May - October

Learn More »

• Most Popular!

Sunset Sail - Licentia

Come join us for an unforgettable cruise on one of our world-class sailing yachts and enjoy the beautiful sunsets in Chesapeake bay!

• Users Up to 6 Passengers
• Hour Glass 2.5 Hours

Your Dream Adventure Awaits

Catering to clients seeking a unique, private sailing adventure for up to six passengers, we offer world-class sailing yachts, decades of experience, and 5-star service to ensure that your charter is truly memorable. All our charters are for private parties, so you can have it your way. is required. 

Charters Feature

Sunset Cruises

Daily Sails

Weekend Cruises

Milestone Celebrations

Marriage Proposals

Family Adventures

Check-out what our Guests say about us! ★★★★★

Capt. Nate & Payton were great! We did an engagement shoot on the boat and they were unbelievably helpful. They were extremely accommodating to the photographer and worked to position the boat perfectly as the sun was setting. Siena is a beautiful boat and the west river is idyllic. Can't recommend enough.

Captain Tony was great host and helped us have a fantastic experience. He even taught my husband some sailing skills, which allowed me to relax, have some snacks and drinks. Boat was clean and very well maintained. He has a strong commitment to saftey and is very knowledgable about sailing. Highly encourage others to book a trip with him.

My fiancé and I are both from New England and grew up by the water, so we knew we wanted a nautical setting for our engagement photos. We had a fabulous time with Classic Sail Charters on the beautiful Siena! Captain was so helpful in offering to angle the boat this way and that for better light and even raising or collapsing sails. We'll definitely be back!

My husband I along with our two grown children (in their 30's), had a wonderful day with decent wind in July sailing at times to 15 knots! Captain Tony was accommodating and friendly. He had a variety of snacks and beverages on board and encouraged participation in sailing the boat as well as relaxing in the sun or shade! We will definitely do this again and we're thinking of also offering this as a gift to my parents who also love to sail.

This past Friday, we joined Capt. Tony aboard the Licentia for an afternoon sailing the Bay. We had a great afternoon sailing and motoring (we lost the wind) around the Bay and through the Annapolis Harbor. Capt. Tony is very knowledgeable, friendly, and helpful. He has loads of sailing experience and all enjoyed his sea stories. Would we go again? Absolutely - planning a trip for next May.

Four of us sailed with Captain Tony on 2 different trips - one afternoon and one morning. Both days were fantastic and relaxing and lovely. The 2nd trip we lost the wind eventually so motored around the Bay and Annapolis and Tony gave us some history and stories. He is delightful and skilled and we had a terrific time. We will definitely plan another trip one of these day.

• New Inventory
• Brokerage Listings
• Why Buy From Us
• Why List With Us
• Testimonials

Catalina 385

Catalina 425

Catalina 445

Welcome to sail annapolis | annapolis, maryland, authorized dealer for:.

Located on the Annapolis Waterfront – Premier Sailboat Dealer for Catalina Yachts & Com-Pac Yachts & True North Power. Serving the Chesapeake Bay & Mid-Atlantic Region

Sign Up For Our Newsletter

Featured Boats

2016 Catalina 385

Price: $271,750

Edgewater, Maryland

2000 Hunter 410

Price: $118,000

Baltimore, Maryland

2021 Hanse 508

Price: $696,000

Annapolis, Maryland

2024 Catalina 355

Price: Request Price

2024 Catalina 425

2024 Catalina 445

We have placed cookies on your device to help make this website better.

You can use this tool to change your cookie settings. Otherwise, we’ll assume you’re OK to continue.

Some of the cookies we use opens in a new tab/window are essential for the site to work.

We also use some non-essential cookies to collect information for making reports and to help us improve the site. The cookies collect information in an anonymous form.

To control third party cookies, you can also adjust your browser settings opens in a new tab/window .

Annapolis Spring Sailboat Show

April 26-28, 2024, join us for the spring boat show in america's sailing capital, annapolis, md..

Are you itching to get on the water? Jumpstart the boating season with the Annapolis Sailboat Show this April 26-28, 2024 .  Annapolis Boat Shows , a leading management company, has been producing these in-water demonstrations since 1970, drawing over 150,000 people from all over the world to the Chesapeake Bay who want to see the latest and greatest in boats and related gear.

The Annapolis Spring Sailboat Show

The Annapolis Spring Sailboat Show takes place Friday, Saturday, and Sunday, April 26-28, at the Annapolis  City Dock . Set in the seaport of Annapolis, it displays catamarans, monohulls, racing boats, and inflatables - with over 100 new and brokerage yachts. Check out the vessels and spend some time shopping for the latest equipment, including electronics, clothing, and other accessories. The show runs from 10 am to 6 pm on Friday and Saturday and from 10 am to 5 pm on Sunday. General admission is $18; children under 12 are free.

Or indulge in an exclusive VIP Experience for $85/ticket. Your VIP ticket includes Boat Show admission and access, with unlimited entry, into the VIP Lounge located inside Latitude 38 Waterfront Restaurant. The lounge includes a full bar starting at noon, continental breakfast, buffet lunch, and afternoon appetizers. Valid for one day only.

April 26 - April 28

Friday: 10:00 am - 6:00 pm

Saturday 10:00 am - 6:00 pm

General Admission ~ $18  ($20 at the gate) Children under 12 are free

For more details, be sure to visit their website . Fair winds and following seas!

Download The Free 2024 Visitor Guide

This handy resource includes a complete listing of accommodations, restaurants, shopping destinations, and more in Annapolis and Anne Arundel County!

Sign Up For Our E-Newsletter

Sign up today and we'll keep you in the loop on upcoming deals, specials, and happenings in and around Annapolis.

STOP BY OUR VISITORS CENTER

26 west street annapolis, md 21401, [email protected], phone: 410-280-0445, fax: 410-263-9591.

Annapolis Discovered

Access annapolis.

• Privacy Policy

©2024 VISIT ANNAPOLIS. ALL RIGHTS RESERVED.

This website uses cookies to enhance user experience on our website. Learn more.

Download our 2024 Visitor Guide!

Plan your stay in Annapolis & Anne Arundel County

Rainbow 24 Sailboat Rental

No trip to the sailing capital of America would be complete without getting out on a sailboat. Our fleet of Rainbow 24s provides a safe and fun experience for those looking to have a relaxing time on the water. Feel free to bring lunch and turn it into a picnic as you pass by the sights with the wind carrying you along.

**Rentals are available during our sailing season: the beginning of April to the second week of October.

Weekdays – $158 (+taxes and fees) for a full day or any portion of a day between 9 am – 4 pm.

Weekends and Holidays – $225 (+taxes and fees) for a half-day between 9 am – 12:00 pm OR 1:00 pm – 4:00 pm

*A 30-minute sailing assessment is required of all new customers. The assessment costs $30 in addition to the rental fee.

Reservations

A reservation is needed to ensure that a sailboat is available when you want to go out. At least two adults are required on a rental boat, one of whom must be a qualified sailor. Up to six people are permitted on a rental boat; no children under 5 years of age are allowed. No pets are permitted.

A late fee of $75 will be charged per half-hour overdue.

• KeelBoat Club Members: Click HERE to jump to KBC Rainbow rental’s booking and information page. You can also click the drop-down labeled “KeelBoat Club Rentals” located under the “KeelBoat Club” tab. Please have your membership ID ready.

Our Rainbow 24 sloops have proven to be nimble, fast, and forgiving. Designed by Sparkman and Stephens specifically for Annapolis Sailing School, the boats are ready to please both novice and experienced sailors. The substantial fixed keel (1100 lbs), cuddy cabin design, and large cockpit combine to produce a boat that is stable, dry, and comfortable.

Qualified Renters

At least one person in the rental party needs to have an ASA 101 certification or its equivalent. New customers must complete a sailing competency evaluation with us prior to their first rental. Renters are required to rig and de-rig their boat. The Rainbows do not have engines, so sailors must be able to depart and dock under sail.

If you need a refresher on rolling and flaking our sails, check out our how-to page here !

Sailing Area

Rentals are restricted to an area close enough to the school so that help can reach you quickly in an emergency situation. Boundaries, determined by management, are subject to change depending on weather and water conditions at the time of your rental. Please understand that going beyond these boundaries makes quick retrieval of the boats difficult in case of emergency. Late returns of boats due to venturing beyond the boundaries will result in late fees. If a renter goes outside the prescribed sailing area and needs to be retrieved, there will be a fee of $75 and the renter will be unable to rent with us in the future.

Sailing is entirely dependent upon wind and weather. We recommend that renters check marine.weather.gov three days before the rental date to see what the forecast is for that day. If small craft advisories or worse are in effect at the start of the rental, the rental may be postponed, canceled, or otherwise restricted at the discretion of the management. In that case, the rental can be re-booked at no additional cost. In low wind situations, you will need to plan your sail so that you can be back at the dock on time.

Cancellations

Rental reservations are charged at the time of booking. Rescheduling within three calendar days of the originally scheduled start of the reservation will result in a $50 rescheduling fee per occurrence. Cancellations made within two calendar days of the scheduled day of the reservation will receive no refund. Refunds are not available for lack of wind.

The boats are covered by insurance. Please inform management of any damage that occurred during the rental. The Lessee has no liability for repairs. However, Annapolis Sailing School is not responsible for personal injury or damage to other boats. You should check your own insurance coverage before sailing.

Other Restrictions

• Children on board must be at least 5 years old
• No alcohol allowed on boats
• No pets allowed on boats
• No swimming off the boats allowed
• No anchoring
• Boats are not permitted to dock at other marinas or facilities other than Annapolis Sailing School

Want to stay in the know about Annapolis Sailing School? Sign up for our new monthly newsletter here to receive information on classes, events, schedules and more!

No thanks, I’m not interested!

Save up to 119.000 €: Discover our offer now

• Open search box

Annapolis Sailboat Show 2024

Hanse Yachts and SAIL magazine are excited to announce Rockstars & Legends , an exclusive event during the Annapolis Sailboat Show. Gain insights from racing rockstar Cole Brauer and cruising legend Lin Pardey, discover the spirit of passagemaking, the impact of self-reliance, and the power of storytelling.

Our cooperation event with SAIL magazine will be held on   Friday, Oct. 11, 2024, 4 P.M. at Jack C. Taylor Conference Center, U.S. Naval Academy, 291 Wood Road, Annapolis, MD. Both the conversation and the QA section, will be moderated by SAIL  Editor-in-Chief Wendy Mitman Clarke and Managing Editor Lydia Mullan. 

Tickets for the event are available in 3 different types:  

Early bird tickets: $50 (Offer valid thru August 1st, 2024) 

Regular Pricing: $65 

VIP Package: $100 (only 50 available, advance purchase is required). 

VIP variant consists of: one event ticket; a special edition of the May issue of SAIL featuring Cole, and the October issue featuring an excerpt of Lin’s new book, Passages, plus the opportunity to meet face-to-face with Cole and Lin, to take photos & take an autograph and for a short chat.  

For more information about the tickets prices & availability, click here .

At this year's Annapolis Sailboat Show from 10-14 October, Hanse Yachts will display the brand new Hanse 360, which is having her US premiere in Annapolis, the Hanse 410 and the award-winning Hanse 460.  For the whole list of Hanse’s yachts available on the show, check out our event page *.  

*Please note that the boat availability may be subject to change  

For more information about the boat show and ticket availability, visit the official Annapolis Sailboat Show 2024 event website . 

Attendees of the boat show are advised to park at the Navy-Marine Corps Memorial Stadium, located at 550 Taylor Ave, Annapolis, MD 21401. Complimentary shuttles will be available to transport visitors to and from the show, operating from one hour before the show opens until one hour after it closes. The box office is located on Dock St., which is the 2nd stop on the shuttle bus.

October in Annapolis Means Boat Shows

This sailing tradition features new and premiering boats, boating gear and accessories, financing options, and fun with fellow sailors.

October 10-14, 2023 City Dock, Annapolis, MD

Thursday, October 10 10:00am – 6:30pm

Friday, October 11 10:00am – 6:30pm

Saturday, October 12 10:00am – 6:30pm

Sunday, October 13 10:00am – 6:30pm

Monday, October 14 10:00am - 5:00pm

Ticket Options

General admission/preview day/ vip experience.

The Annapolis Sailboat Show is located at City Dock in Annapolis, MD.

The Box Office is located on Dock St. (2nd stop on the shuttle bus)

GPS: 1 Dock Street, Annapolis, MD 21401. 

View In Google Maps

Boat show visitors are encouraged to park at the Navy-Marine Corps Memorial Stadium (550 Taylor Ave, Annapolis, MD 21401) and take a free shuttle to and from the show. Shuttles will run one hour prior to show opening through one hour after the show closes.

Pre-sale of Stadium parking is offered at the discounted rate of $23 per day, $43 for oversize vehicles. Pre-sale of parking closes at 10 PM the evening prior to the day you plan to attend. After that, you may purchase parking onsite at the Stadium Gate 2 entry located at 200 Farragut Rd for $25/$50, credit card only. No cash will be accepted. Please click the link below for access to ParkMobile where you can reserve parking.

Parking is also available in the parking garages in downtown Annapolis . Be sure to plan ahead as parking garages downtown fill up fast. 

Reserve Parking

2024 Show Guide will be available in late September.

Looking for the inside scoop on the 2024 Annapolis Powerboat Show?  Join our email list for updates  on new exhibitors and programming – it’s free and you can unsubscribe at any time!

Known as the “Sailing Capital of the World”, Annapolis’s maritime history, nautical culture, and an exciting atmosphere make it the perfect location for boat shows. When guests have finished exploring the floating docks and shoreside exhibit areas, downtown restaurants, shops, and galleries open their doors to these sailors looking to extend their stay. Make your plans now and book accommodations.

• Plan Your Trip
• Where is the Box Office? We encourage our customers to skip the lines and buy online. If you do need to purchase at the gate, please exit the shuttle bus at the 2nd stop. The Box Office is located on Dock St.
• Are pets allowed on show grounds? No, animals are not allowed inside the show due to safety and health reasons unless it is a certified service animal.
• Are strollers allowed on show grounds? No, strollers are not allowed inside the show due to safety issues. Please park your stroller in the designated stroller parking area.
• Should my child wear a life jacket? Yes, we recommend all children wear life jackets for their safety.
• Will the show be open if it rains? Yes, the boat show happens rain or shine.
• Can I scan my ticket from my phone? Yes, you do not need to print out your ticket. All tickets may be scanned from your phone.
• Are backpacks allowed in the show? Yes, backpacks and bags are allowed.
• If I leave the show, am I allowed back in later? Yes, you will receive a hand stamp that will allow you to re-enter the show without your ticket.
• Can I bring food or drink into the show? Yes, you may bring food and drinks into the show.

Tickets are on sale now!

• AROUND THE SAILING WORLD
• BOAT OF THE YEAR
• Email Newsletters
• America’s Cup
• St. Petersburg
• Caribbean Championship
• Boating Safety

The Rise of Harbor 20s In Annapolis

• By Gary Jobson
• July 9, 2024

during a walk along the Annapolis shoreline a few years ago, I noticed a fleet of boats racing on the harbor. From a distance, it looked well-organized and plenty competitive. And as I watched them go around the usual channel buoys that they were using as race marks in an orderly fashion, I wondered who it was who had been responsible for getting this fleet started from scratch. We all know that it can be difficult to run a local racing fleet, never mind to start one, but we also know that behind every successful fleet, there’s usually a spark plug or two, the heroes of our local fleets, and as expected, the fleet that I observed that day on my shoreline stroll has theirs.

As one of the more successful and newer fleets to take hold in Annapolis, the Harbor 20s sailors make up the tightknit community of Fleet 5. Initially, there were a handful of Harbor 20s that raced PHRF back in 2005, but in 2011, local yacht broker Garth Hichens sold a group of sailors on the idea of creating a one-design class in Annapolis. The Harbor 20, built by WD Schock in California, is best-suited for either two or three crew, and the class has strong pockets in the US, especially venues with protected harbors for which the boat was designed. It’s meant to be a simplistic daysailer, so Hichens and the group agreed to make it a nonspinnaker class. Its self-tacking jib-boom makes things even easier on the crew.

Fleet 5’s early adopters comprised novice racers to skilled veterans, and fleet ­members made sure that the social aspect was a priority. The endeavor quickly encouraged more local sailors to acquire boats, and as a result, the fleet grew rapidly. But it also needed structure to ensure fairness and long-term viability, and two successive fleet captains have provided the leadership and resolve to maintain governance of the fleet, organize racing logistics, and work to improve the competitive level of the ­racing and to grow the fleet.

Enter Annapolitan Bell Carty, who comes from a racing family and was named fleet captain just as the COVID-19 pandemic was sweeping across the country. She says that it took quite a bit of work to get the fleet organized. “I inherited a fleet that was thriving, but there was little structure,” Carty says. “We had a lawsuit to deal with, and we needed insurance and a better way to communicate.”

Retired attorney John Heintz, who was one of the early Harbor 20 owners in Annapolis, stepped forward to help resolve the lawsuit with the builder in California, and he worked on an insurance policy for the class and the sailors themselves. “After the dispute was eventually  resolved, we incorporated our local fleet and secured appropriate insurance for both the class and the fleet for the first time.” 

Then came the communication challenges, which Carty says was a result of too many means of outreach to fleet members. “We created a website and pushed all our messaging through the site,” she says. “If something happens, it’s important to keep in touch to reduce any tensions that might arise. We make sure to communicate with everyone, not just the fast sailors, so no one is left out. We also make sure that everything we are running is fun.”

Heintz is keen on the fleet’s regularly scheduled Thursday coffee-and-breakfast gatherings at Annapolis YC, which follow each Wednesday-night race during the summer. The topics vary, and open discussions help resolve contentious issues, which, if left to fester, can create more headaches later on. “People can express their views in a thoughtful way,” Heintz says. “We are a group of friends trying to keep it that way. If necessary, we consult with people outside the class.”

Carty adds that it was important for the fleet to write a set of bylaws and determine an appropriate owner-driver fleet policy. They also designated that higher-level regattas would mandate that the boat owner be at the helm when racing. It’s also important for the fleet to vary the style of races, she says, so not all of them are windward-­leeward. Sometimes they’ll simply have an informal race to someone’s house on the water.

While Heintz spent his early years practicing law, he cruised his C&C 39 for 14 years with his brother, and then his Saga 43 with his wife for 15 years, mostly transiting between the Chesapeake Bay and Maine. “I got into racing late in my career,” he says. “As the fleet grew around me, others came along to challenge me. I’ve learned from watching.”

The Harbor 20s sail very close to each other on short courses, he says, so it’s easy to measure one’s performance against others. “Everyone in the fleet will give you pointers or sail with you,” he says. “We recently had a seminar with two of Annapolis’ best sailors, Jonathan Bartlett and Will Keyworth, who shared images of our boats so that we could analyze sail trim and talk about tactics.”

There are currently 34 boats registered in the Annapolis Harbor 20 fleet, and Heintz says that there is a spike of interest in the boat of late. “Recently we had two top local sailors join, J/24 champion Tony Parker and Etchells standout Jose Fuentes-Afostini,” he says. There are only two limitations to growth: “finding available boats and then finding a place to put them.”

The fleet is working with the Annapolis YC to juggle more space in its dry sail storage lot to accommodate additional Harbor 20s on trailers. Carty says that the fleet runs races about 80 days per year, usually for one-day regattas, so as not to burn out fleet members. “We go out about three days per week,” Carty says. “One-day regattas are the most popular in our fleet. It is a real challenge to sell a two-day regatta, but they are good practice for multiday events like the East-West Challenge or the National Championship.” 

The annual East-West Challenge is a highlight for the more-competitive Harbor 20 devotees in the US—a fleet-race championship that pits teams from the East Coast Harbor 20 enclaves of Annapolis; Hilton Head, North Carolina; and Charlotte Harbor, Florida; against those from the west, including Santa Barbara and Newport Beach’s Fleet 1. 

One of the most difficult challenges for one-design-fleet spark plugs anywhere can be measurement compliance, especially when the vibe is meant to be low-key but also fair. Heintz says that Annapolis’ fleet has been smooth sailing since the beginning. “We haven’t had any issues with measurement or compliance,” he says. “People came from other one-design fleets that are more contentious. Now they want a boat that is simpler and fun to race. They are at that point in their lives.”

Hichens, he adds, has been instrumental in leading fleet-boat maintenance and issues with keels and rigs. “We hosted the nationals and followed the class regulations,” Heintz says. “All 25 boats were weighed and measured, and we set limits for adjustments.”

Several of the Annapolis-based Harbor 20s are owned by partners who alternate turns at the helm, which helps keep as many boats on the water as possible. The Wednesday-night summer-series starting line has become so crowded, however, that the fleet decided to parse into two divisions. Their solution for dealing with overcrowded starting lines and racecourses might serve as an example for other clubs looking to take the stress out of their more-casual racing series.

 Fleet 5’s summer season, for example, is divided into three different series of five-week intervals. The roster of each of the fleets is drawn out of a hat for the first set of the series. The divisions then switch for the second series, with the odd-numbered finishing boats switching fleets. The third series is made up of the top-half finishers of the first two series racing together for the championship.

This protocol allows teams who regularly finish in the bottom half of the fleet to compete against boats of the same caliber and have a chance at finishing in the top tier. The experiment during summer 2023 was very successful and will continue during the Wednesday-night series this summer.

The combination of competitive but relaxed racing and popular fleet social events attracts many sailors who are not regulars on the grand-prix circuit. Crews include many couples or parents with children. Carty, for example, often races with her 84-year-old father, George Hughes. Her son, also named George, just finished his first year at the United States Naval Academy and races when he gets leave from his midshipman obligations. Keeping with the fun theme of the fleet, she says, “Carty is for party, with a C.”

• More: One Design , Print Summer 2024 , Racing , Sailboat Racing
• More Racing

Newport Bermuda Race Goes the Way of the Classic

Windmills Plane and Simple

Melges Expands Into Florida with Watersports Center

Winners Debrief: Melges 15 Winter Champs

Twelve Inductees Headed to National Sailing Hall of Fame

Black Foils Pad Season Lead with SailGP New York Win

• Digital Edition
• Customer Service
• Privacy Policy
• Cruising World
• Sailing World
• Salt Water Sportsman
• Sport Fishing
• Wakeboarding

• Food & Drink
• Best Restaurants 2024
• Best Restaurants Readers’ Poll Results 2024
• Arts & Culture
• Bmore Social
• Weekend Lineup
• July Lineup
• Community Calendar
• News & Community
• History & Politics

GameChangers

• Science & Technology
• Education & Family
• Business & Development
• Best of Baltimore Party 2024
• Best of Baltimore Readers’ Poll 2024
• Best of Baltimore Editorial Picks
• Best of Baltimore Weddings Readers’ Poll
• Health & Wellness
• Top Docs Nominations 2024
• Style & Shopping
• Travel & Outdoors
• Home & Living
• Home & Design Awards Finalists 2024
• Real Estate
• The Wedding Party 2024
• Current Issue
• Vendor Guide
• Real Weddings
• Submit a Wedding
• Restaurants
• Newsletters

© 2024 Baltimore Magazine

The material on this site may not be reproduced, distributed, transmitted, cached, or otherwise used, except with the prior written permission of Baltimore Magazine.

Paul Bollinger Helps Individuals With Disabilities Experience the Joy of Sailing

The president and ceo of chesapeake region accessible boating—a lifelong boater who founded the wounded warrior sailing regatta in annapolis—discusses the organization's work..

By Ron Cassie | GameChangers 2024

How long did it take to raise the money and put the financial deal for the land and construction together? Waterfront property in Annapolis is not cheap real estate. The CRAB board made the decision to start looking for a new facility when we went from four boats to six in 2017. We had filled the floating dock at Sandy Point State Park. We hoped to be in Annapolis, although we looked throughout Anne Arundel County. Finally, we found a property and marina that the owners were interested in selling, and then we worked with them over many lemonades shared on the front porch, talking with them about our plans and the process that we had to go through to acquire the property.

It must be a tremendous feeling to be on the water for people who use a wheelchair. Many, I assume, have never sailed previously. There’s one story that almost brings tears to my eyes every time I share it. I was in the office working, and one of our young skippers—and we don’t have a lot of young ones, we’re always looking for those—calls me. He says, “Hey, I wanted to let you know that I just took a young guy out sailing.” And he says they were sailing near the Bay Bridge when our guest with disabilities turned and looked at him and said, “I want you to know that I really appreciate you taking me the farthest I have ever been from my wheelchair and the memories that put me in it.”

Local News | How some of Annapolis’ leaders will be…

Share this:.

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

Capital Gazette eNewspaper

Local News | How some of Annapolis’ leaders will be celebrating Independence Day

Mayor Gavin Buckley will watch the fireworks with friends and family from a boat.

“There aren’t many places in the world where a guy with a funny accent could land in young adulthood, make it a place to call home, and be lucky enough to be elected mayor of a capital city,” said Buckely, who moved to Annapolis from Australia in 1992 and is a Democrat. “Independence Day is a day to be reminded of how lucky we are to live in a place that is so welcoming.”

Lisa Rodvien, an Annapolis Democrat on the County Council, will be visiting parades all day. Her family ends the day each year watching the Annapolis fireworks from their driveway. Rodvien appreciates the day because it’s an opportunity to reflect on the sacrifices so many have made to protect our freedoms.

“If you want to feel a great sense of gratitude and awe, look them up. Their courage was extraordinary,” said Rodvien in a statement. “I will not pretend we are not a perfect nation, but we owe it to those who sacrificed so much to strive to make it better.”

Dana Jones, an Annapolis Democrat who represents District 30 in the Maryland House of Delegates, said her family enjoys the holiday’s sense of collective pride and celebration. They will end the day by watching the fireworks in Annapolis.

“I can’t wait to share this special day with folks from across the city and county,” said Jones.

Scott Schuetter, owner of Shrek Realtor and Crew in Annapolis, will gather with his friends and family starting Wednesday night. They plan to shoot off their own small fireworks and jet ski before heading to the Sherwood Forest fireworks show. Schuetter, a U.S. Naval Academy graduate, will continue the fun with his family on the Fourth of July, with more festivities planned on the beach, where they will have a view of the Annapolis fireworks.

Chris Townsend is the director of food and beverage at Pussers Caribbean Grill, which will be closing later this year after 30 years on the dockside. He will be working on the Fourth of July and expects 1,000 customers.

“It’s been an honor to be a part of the community and a part of the festivities of the Fourth of July downtown with the fireworks,” said Townsend. “The town’s going to be electric.

“It means lots to us, how much the community has been there for us and supporting us through this last year. We’ll try to make as much fun as we can and make it a happy occasion and not a sad occasion,” said Townsend.

More in Local News

Sports | Bob Cawood: Terrapin Park on Kent Island a great location for a trail run | RUNNING COMMENTARY

Environment | Kids on the Creek splashes back into Eastport after three-year hiatus

Local News | Lactation pod at Annapolis Mall library is a first for Maryland

Local News | 6-year-old killed, 2 adults injured in shooting at July Fourth party in Prince George’s County