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Sail the Florida Keys

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Get Away to Key West and Explore the Florida Keys by Sailboat

Did you know there's an international airport perched out in the Gulf of Mexico at Key West? Serviced by all major US airlines and with frequent flights from main airports in the East and South, Key West is so easy to get to. That's where you'll find our boat charter operators, who have a range of sail and motor boats for you to explore this unique corner of the USA.  

Along the Florida Keys the holidaymaking options are numerous. Enjoy the aquatic environment with countless opportunities to snorkel, swim, kayak, paddleboard and more, while totally relaxing on board, or ashore on one of the Keys' beautiful beaches. Enjoy an evening meal in one of the upmarket restaurants that dot the Keys, shop and enjoy the nightlife in the major centers of population, and get close to nature at one of several locations designated State Parks. 

While pandemic concerns are limiting travel options, consider Key West as your next boat charter vacation destination. Local ordinances reflect the need to keep everyone protected and make this a safe destination. The communities are welcoming and open for business. 

Some of the highlights to experience on a Florida Keys Sailing Charter Vacation 

Your Florida Keys adventure likely begins and ends at Key West, which is closer to Cuba than Miami yet connected to the US mainland by the 90-mile long Overseas Highway that's an experience in itself. Most sailing charter visitors arrive by air and take the short transfer to one of the charter bases located on the island. Famous for its coral reefs, local architecture, historic sites and nightlife, charming Key West is well worth some time before or after your charter.  

Like most charterers however, you will probably be keen to go sailing and start exploring the chain of cays that make up this most southerly part of the Continental USA. Two great things about sailing here are that distances between attractions can be as short as you'd like them to be, and anchorages are plentiful, if shallow in places. A seven-day charter Key West to Key Largo and return is easily achievable. 

Travelling out of the Stock island marina, it's less than 30 nautical miles to Baihia Honda Key, a popular stopover. In the vicinity there's a variety of stunning beaches, some say the best in the world. Looe Key has some of the best snorkelling you'll experience on your vacation. 

A similar distance to that travelled above will take you from Bahia Honda Key to Long Key, via Marathon, a major sport fishing town of 10,000 people surrounded by the bountiful sea. Stop a while and enjoy a seafood lunch, or you may prefer to do Marathon on the return. At Long Key enjoy the natural surroundings, the greenery and the birdlife. 

Perhaps after two days of sailing that have taken you from Key West more than half way to the mainland, you're ready to take it a bit easier. Less than ten nautical miles onward you'll come to Indian Key Historic State Park at Islamorada. Nearby is the San Pedro Underwater Archeological Preserve, another one of the numerous state parks along the Keys. The San Pedro was a Dutch ship sunk during a hurricane in 1733. What remains lies in 18 feet of water 1.25nm south of Indian Key, easily accessible to good swimmers. 

From Indian Key, it's a further 20nm sailing distance to Key Largo. Apart from the shops, bars and restaurants, most of the attractions are aquatic-based as they are all along the Keys. A visit to the Florida Keys Wild Bird Rehabilitation Center can be rewarding, a reminder of the fragility of nature in this delicate place. 

If you enjoy walking while on vacation, the Florida Keys Overseas Heritage Trail is accessible to many points along your sailing route. 

Browse our yachts for charter in Florida Keys

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• Matching any competitive offer
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• 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.

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Private Liveaboard Classes

Florida keys sailing, come sail with us.

Proud Member of the ASA

At Florida Keys Sailing our specialty is: Private Live Aboard Sailing Classes and Sailing Vacations with just you and your spouse or friends. “Learn to Sail” or take an Advanced Class to develop your skills. Qualified sailors can Charter our boats. A Captain will happily take you and your family on a Day Sailing Trip if you need one. Many sailing classes offered elsewhere crowd you on a boat with a group of total strangers.

At Florida Keys Sailing ALL of our Sailing Classes, Day Sailing Trips, and Private Charters are exactly that…PRIVATE.

No one else except YOUR Party is ever on-board. This means you will learn more by having more time DOING, not WATCHING someone else sail. Dollar for dollar you will find more VALUE in taking your Sailing Courses at Florida Keys Sailing.

Fun on the Waves

Our Classes

To learn more about the liveaboard classes we offer, visit our classes page

2 DAY BASIC FUNDAMENTALS OF SAILING

Designed for beginners who want the best introduction to the exciting sport of sailing. Students will receive a good understanding of all the “Basic Fundamentals of Sailing”. They will leave as very competent Crew Members.

3 DAY BASIC KEELBOAT “LEARN TO SAIL CLASS”

Beginner students will learn to responsibly be the Skipper of a Day Sailing Keelboat in familiar waters in moderate wind and sea conditions. Classes available are year round on demand based on your travel plans.

5 DAY BASIC COASTAL CRUISING OR 101 & 103

Students will learn to responsibly skipper and crew an auxiliary powered cruising sailboat during daylight hours within sight of land in moderate wind conditions. This Private Live Aboard Class is taught aboard our Catalina 30' or Irwin 34 Offered all year on demand based on your travel plans.

5 DAY BAREBOAT CRUISING OR 103 & 104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34. Offered all year on demand based on your travel plans. 5 Days and 4 Nights…Privately Living aboard at our Dock

3/1 DAY ADVANCED COASTAL CRUISING OR 106

Cruise a sailboat during nighttime hours in most wind and sea conditions. A Private Live Aboard Class is held aboard our Catalina 30 or Irwin 34. Offered all year on demand based on your travel plans. 3 Days and 3 Nights…Privately Living Aboard

7 DAY BAREBOAT CRUISING OR 101, 103 &104

Charter a cruising sailboat during daylight hours in most wind and sea conditions. This Private Live Aboard Class is taught aboard our Irwin 34 This is the Class the Bareboat Charter Companies want you to have. Offered all year long on demand based on your travel plans. 7 Days and 6 Nights…Privately Living Aboard at our Dock

3 DAY FAST TACK TO CRUISING ASA 101 & 103

It’s the fastest and least expensive way to get the first 2 – ASA Certifications. Both combined into a 3 Day / 2 Night Live aboard Class. Prior sailing experience before enrolling is advised.

5 - DAY FAST TACK TO BAREBOAT CRUISING ASA 101, 103 & 104

It’s the fastest and least expensive way to get these 3 - ASA Certifications. All 3 are combined into a 5 Day / 4 Night – Live aboard Class. Prior sailing experience before enrolling is advised. A second student enrolls for FREE!

Testimonials

Daysailing & charters, we offer both daysailing and charters, click below to learn more.

• SAILING LOCATION: Keys Fisheries & Marina 35th St Gulfside, MM 49 Marathon, FL 33050
• By Mail: Florida Keys Sailing 5171 Overseas Hwy #504407 Marathon, FL 33050
• By E-Mail: [email protected]
• By Telephone: 305-619-0140
• Marathon Chamber of Commerce
• Get Knotted - Animated Knots
• Sombrero Lighthouse Data and Marine Forecast

Copyright© 2020 Florida Keys Sailing™, LLC

 Key West & Marathon, Florida

We specialize in private luxury yacht & sailing charters at affordable prices. we offer day charters as well as multi-day charters., why blue ocean yacht charters.

Blue Ocean Yacht Charters, located in Key West, Florida, makes yacht rentals affordable and life-changing.  We offer private multi-day bareboat charters to amazing destinations like The Dry Tortugas and the Florida Keys.  Just looking for a day charter?  Look no further.  We offer four hour, eight hour, and 24 hour charters as well multi-day charters.

All our yachts come fully equipped to make your private boat charter experience what you’re looking for. We offer motor and sailing yachts that provide the best boat rental experience.  

Florida Keys Yacht Charter

Embark on a unique yacht charter adventure in Key West and the Dry Tortugas. Discover history, pristine natural beauty, and thrilling offshore passages.

Discover: Florida Keys

Florida Keys & Key West: A charterers' delight with vibrant city life, the remote Dry Tortugas National Park, and underwater treasures waiting to be explored.

Key West offers more than just a lively city - it's a gateway to secluded Dry Tortugas, rich marine sanctuaries, and unforgettable offshore adventures.

Chart your course with confidence

Explore our handcrafted Florida Keys sailing itinerary.

Sail from bustling Key West to serene Dry Tortugas. Dive into history at Fort Jefferson, snorkel at Windjammer Wreck, and savor the majestic sunsets over Marquesas Keys

Florida Keys: explore what awaits you

Uncover the cruising conditions you can expect out there on the water and the various sailing seasons for this stunning destination.

Unlock in-depth Florida Keys yacht charter insights

Explore our latest Florida Keys blog posts to get a deeper understanding of its hidden gems.

Summer reads: nautical adventures & high-seas thrills

To help build your summer reading list for those relaxing moments on the beach, I’d like to share some books I highly recommend that I’ve read in the past.

What is the Distance from Key West to the Dry Tortugas?

Discover the distance from Key West to the Dry Tortugas in our guide including essential sailing insights for a successful yacht charter.

Key West Bareboat Charter | Sailing Adventure to the Dry Tortgas

Our 2021 Key West bareboat charter and sailing adventure to the Dry Tortugas. Great fishing, long passages, and plenty of history.

Florida Keys frequently asked questions

Have more questions? Visit our comprehensive FAQ page for detailed answers to common Florida Keys charter questions.

Key West offers a variety of provisioning options, from supermarkets to specialty stores. Visitors should plan to stock up on necessities since there are no provisioning options in the Dry Tortugas.

Sailors can enjoy steady trade winds and warm, comfortable temperatures year-round in Key West, with the best sailing conditions from December to May, avoiding the peak of hurricane season from June to November.

During the hurricane season, it's crucial to monitor weather forecasts closely and have flexible plans, as tropical systems can develop rapidly, potentially affecting sailing itineraries.

Fishing in the Dry Tortugas National Park is regulated, with certain areas designated as no-take zones. Anglers must familiarize themselves with and adhere to these regulations to ensure sustainable fishing practices.

Anchoring is restricted to protect the coral reefs and marine habitats. Visitors must use designated mooring buoys in specific areas within the Dry Tortugas National Park to minimize environmental impact.

Explore pristine shores and hidden gems

Unveil the best of Florida Keys, from secluded beaches to enchanting islands and serene anchorages.

Boca Grande

Anchor off Boca Grande for breathtaking sunsets and a peaceful night under the stars.

Discover the best marinas, provisioning options, nightlife, and anchorage spots in Key West for yacht charter crews, the gateway to the Dry Tortugas.

Marquesas Keys

The uninhabited Marquesas Keys offer a serene escape with spectacular natural beauty, perfect for a day in solitude or a stopover from the Dry Tortugas.

Florida Keys charter planning?

Consider booking with the Yacht Warriors.

Private & Shared Sailing Charters

Sunset sail key west.

Have the sea to yourself with Sunset Sail Key West—chartered sailing trips led by us, tailored to you.

Get inspired with our most popular trips!

Private sunset sail.

Chillout Lilypad Sail

Key West Daysail

Sunset Sail on When & If

Privates Charters

Discover your perfect private charter.

Set out on a snorkeling, stargazing, or sunset sail, or build your own custom trip. Romance, relax or unwind from the privacy of your own chartered sailboat.

Shared Trips

Come together on a shared charter.

Rise above the crush of the crowds and set sail on a unique shared sunset charter, with a few friends you haven’t met yet. A personable local crew and captain will treat you to a stunning sunset view from the deck of an unforgettable vessel– General Patton’s elegant, private schooner When and If.

Three Classic Boats

View our fleet.

We sail a fleet of three vintage sailboats, each with their own unique charm and appeal. A custom sloop, a classic ketch, and a historic schooner are waiting to make memories with you on the crystal clear waters of Key West. Each boat is suited to different types of outings, so take a moment to get acquainted with our vessels.

Real. Fun. Sailing.

When And If is back at beautiful Stock Island Marina!

Check Out Our Ship's Store!

Wreckers' Race Season Is Back!

Hello, Sailor! Don’t miss out on the latest Sunset Sail news & offers.

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Legal & safety.

What Should I Bring?

• Directions to Echo, Cruise Ship & K.W. Passenger Info

Key West Info

• Cancellation Policies, Terms and Conditions
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• Echo 2 Private Day Charters
• Echo 3 Private Day Charters
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• Tasting Notes
• Sunset Cruise

$10 Off each person – Promo Code “EchoDirect”

(for Public trips only – sold by the seat)

Catamaran ECHO 2

Current public & private trips – book here online, (free shuttle to the echo 2 dock from the perry hotel).

Catamaran ECHO 3

Custom private charters – book here online, regularly scheduled public & private trips starting soon, …is a fast and comfortable sailing machine, providing the most stable ride on the water. naturally it’s a catamaran.

And with our big bimini top, you can get all the Key West sun or shade that you want. The fresh water shower on deck comes in handy on those hot days. A private bathroom in the cabin makes a day in the wildlife refuge civilized and helps protect our tropical waters.

ECHO 2 is located at the “Key West Historic Seaport” which is downtown in Old Key West at the famous Key West Bight. The Historic Seaport “Harbor Walk” goes right around the water’s edge and leads right to ECHO’s dock along side the famous “Boat House Restaurant at Turtle Kraals”. Spend the day on the Harbor Walk before and after your ECHO trip and visit all the great shops, restaurants and bars and galleries. This is where all the locals hang out!

So come and hang out in the coolest part of town and cruise with us at Catamaran ECHO ..

ECHO'S Official Website

Wild Dolphin

Snorkeling & Sailing Adventure

Click here to read more!

Private Day Charters

2 to 19 Passengers

Sunset Cruise - Adults Only

Private Trips Available (all ages welcome)

Towel (day trips), Sun screen applied (no oil), Hat, Camera, Sunglasses (polarized best), a jacket in fall, winter, spring (even if you think it’s warm out), a small bag to secure your things, a few bucks and a Big Smile!

Echo Upgrades

Please reserve upgrades in advance while reserving here online, or by phone or email before the trip.

Directions, Cruise Ship & K.W. Ferry Passenger Info

Certificate of Excellence 2019

Read Reviews

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1-888-579-4782.

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Our Activities

Catamaran Echo - Wild Dolphins! Snorkel & Sailing Adventure

Catamaran Echo - Sunset & Moët Cruise

Catamaran Echo - Private Day Charters

Catamaran Echo - Private 2 Hour Champagne Celebration Sunset Sail

• Chesapeake Bay Itineraries
• Key West Itineraries
• Chesapeake Bay
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Key West Sailing Charters

Experience the beauty and wonder of an unspoiled tropical paradise without ever leaving the Continental United States. Our Key West sailing charter destination is located minutes from all the downtown Key West attractions and Duval Street night life, yet a short sail away from pristine reefs, underwater nature preserves, and uninhabited island locations such as the stunning and secluded Marquesas. Kayak, paddle board, and snorkeling excursions will open to you the offshore beauty offered only in the Florida Keys. Our native Floridian staff knows how to find the best activities on land or at sea, to guide you as you plan a unique and customized getaway.

Our Key West Sailing Charter Fleet

Sailing cats.

Southern Cross

Fountain Pajot Elba 45

Dream Reach

Sugar Magnolia

Seawind 1260

Second sight.

Stay Glassy

Nautitech 40 open.

Ever Summer

Fountaine pajot my44, key west attractions.

Historic Duval Street

One of the most popular destinations on the island of Key West is Duval Street. Visit the Ernest Hemingway Home and Museum where you can take in some history about the writer and meet a legendary six toed cat. If you feel like taking in some nature, visit the Key West Butterfly and Nature Conservatory where there are 50 - 60 different species of live butterflies from around the world. On Duval Street, you can simply take a stroll and hear live music, see art galleries, enjoy coffee shops and great restaurants, or find unique souvenirs at one of the many boutiques.

Romantic Sunsets

Beautiful sunsets are what Key West is all about. Enjoy the soothing ocean breeze, a glass of wine, and relax to the backdrop of the setting sun on your own private catamaran cruise. Watching the sunset has become an integral part of everyday life in paradise. This is one tradition you don’t want to miss!

Crystal Clear Snorkeling

Key West offers many beaches and reefs where you can experience snorkeling in warm crystal-clear water. At Cottrell Key, see the unique sponge garden and large coral reefs. It is also an excellent place to see dolphins, sharks, stingrays, and Goliath groupers. Fort Zachary Taylor is considered one of the best offshore snorkeling spots in Key West where there are a variety of tropical fish species and living coral to see. A favorite among snorkeling enthusiasts is Sand Key Lighthouse Reef. With a remote location and strict no-take policy, the Sand Key Lighthouse Reef is one of the healthiest coral gardens in Florida.

Pristine Sandy Beaches

Craving a drink in your hand and your toes in the sand? Check out the turquoise waters at Smathers Beach. Rental shops are available with beach chairs, shade umbrellas, kayaks, jet skis and much more. Try South Beach for calm, shallow waters that are excellent for swimming and great for families. Higgs Beach is unique for its historical significance. Take a wander around, and you'll find monuments dedicated to the 19th-century slave cemetery located on the site. There is also a pier at Higgs Beach, where visitors can often spot stingrays and other marine species.

Key West Sailboat Charter Aboard the Tamboo

Our Fleet: the Tamboo

Bareboat or captained charter ~ asa sailing courses*, ocean's edge marina key west, florida 2023 bali 4.2 sailing catamaran 4 cabins - 4 toilets w/sinks - 2 showers 8 passengers max. or 6 passengers maximum if charterer selects and pays for a captain., *charterer selects and pays for an asa qualified captain for asa training..

Specifications

Cabins/berths Toilet w/sink Shower stalls

Beam Draft Water Capacity Fuel Capacity Engine

4 - (8 occupants max.)

23'6"

5' 227 US Gal 169 US Gal

2 x 45HP Yanmar

Interior Features

Air Conditioning

Interior Fans

Generator power

Solar power

Fridge/Freezer

Freshwater Filter

3 burner cooktop

Freshwater electric toilets

Exterior Features

Cockpit Cushions

Bimini Over Helm

Dinghy on Boat Lift

Forward Lounge

Swim ladder

Helm Lounge

Built in BBQ Grill

Fully Equipped Galley

Dishware, Silverware, Cutlery, Cooking Utensils

Serving bowls, platters, pitcher, cookware

Cutting Boards (*please provide your own cutting board, filet knife & cooler for fish*)

Small Appliances such as Coffee Maker,

Blender, Toaster, Microwave

Starter supply of paper towels, dish soap, fresh sponge

Linens & Things ​

Bed Sheets & Blankets (beds will be fully dressed upon arrival)

2 Bath, Wash & Hand Towels per guest

Starter supply of marine grade toilet paper

Navigation Equipment

Apparent wind indicator

Depth sounder

RAYMARINE AXIOM+ GPS/chart plotter

Hand Bearing Compass

Parallel rulers

Stereo/cockpit speakers

VHF mic at helm

Local charts

Cruising Guide to Florida Keys

Florida Keys Sailing

The Spanish first found the Keys during Ponce de Leon's expedition in 1513. They mapped and named the Keys principally as an aid to their ships, which, full of gold and silver, used the Florida Straits to go from the New World back to the Old. The first settlement was at Key West, in 1882, a little more than two decades before Florida became a state. The other Keys pretty much stayed deserted until 1874, when the government surveyed them. After the survey, the government plotted land for businesses and homes. The early homes were primitive. They were built from the local beaches, made of wood and other materials washed up from shipwrecks. In 1912 Henry Flagler built a railroad to Key West. This greatly increased human settlement of the Keys. The railroad was destroyed by a hurricane in 1935, but in 1938 the longest over-water road in the world was built on the railroad's foundation. It includes 42 bridges--one that is seven miles long! This opened the Florida Keys up to a growing tourist trade.

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Florida Keys Catamaran Yacht Charter

Catamaran yachts for charter in florida keys.

Browse a unique selection of Florida Keys Catamaran Yacht Charter and embark on the most exclusive luxury retreat. The tranquillity of cruising, coupled with the warm crew’s services, gourmet cuisine, and tailored itineraries, encapsulates the essence of opulence that Florida Keys is renowned for, creating unforgettable memories on the gentle Florida Keys tides.

Enquire On Florida Keys Yacht Charter

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FLORIDA KEYS YACHT CHARTER

Get away from it all with a Florida Keys yacht charter to your enchanted island paradise. Stretching over 120 miles, the Keys consist of over 800 chartered islands packed with vibrant culture and surrounded by crystal-clear waters.

The best snorkelling and diving sites in the world await you all along the Florida Keys, which even boasts the only living coral barrier reef in North America. With so much to see and do, you’ll be glad your luxury yacht crew offers world-class service and expert guidance to help you enjoy an experience you’ll never forget.

It’s no wonder why these gorgeous islands are a favorite yachting destination. From exceptional deep-sea fishing to hidden beaches, picturesque sunsets, and dynamic nightlife, expect to create a lifetime of memories in just one Florida Keys yacht charter.

YACHTS FOR CHARTER IN THIS AREA

• Tour Dry Tortugas National Park
• Visit the Ernest Hemingway Home and Museum
• Explore the mangroves of Marquesas Keys
• Spend some time at the Florida Keys National Marine Sanctuary
• Go see the turtles at The Turtle Hospital
• Have a drink or two at Irish Kevin’s
• Stroll through Key West Butterfly and Nature Conservatory
• Watch the sunset at Mallory Square
• Listen to live music on Duval Street
• Snorkel at Cheeca Rocks

Yachts for charter

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Bareboat Charter

A bareboat charter means the charterer, as Captain, is solely responsible for the safe operation of the vessel, including all aspects of navigation, anchoring, docking, and controlling the vessel under sail or power. Key West is considered an advanced sailing destination and for the safety of other passengers and the vessel, it is vital the charterer have sufficient experience aboard vessels of a similar size & type as what you are seeking to hire. We also require there be one other person aboard to act as first mate, with enough boating experience to handle the vessel in the event the Captain is injured or goes overboard.

All of our bareboat charters have a 4 day/3 night minimum which is the ideal amount of time to experience one of our Florida Keys sailing itineraries .

Am I qualified?

Sail with confidence, am i qualified for bareboat charter.

The Florida Keys is considered an advanced sailing destination, offering great natural beauty in sometimes rare peaceful isolation. There are almost exclusively anchorages in our cruising grounds subject to tidal changes and currents, including open anchorages in the Westerly Island groups.

Our bareboat charter application will help us evaluate your sailing experience to establish your skill level, and that of your first mate, as suitable to these conditions. This application should be filled out in full, providing as much information as possible to validate your skills and experience. Please submit the requested documents together in order to complete the application process. No booking should be considered confirmed until this application has been approved by the reviewing Charter Base Manager. You may be contacted directly to answer any questions they may have.

Bareboat Charter General Qualifications & Requirements

•30 days or 400 miles in the last three years as named Captain on an equivalent size & type of yacht(s).

•ASA, US Sail, RYA or ICC certification to an equivalent Bareboat Charter level for Monohull & Multi Hull for Catamaran.

•Physically capable of handling the vessel in all situations & conditions (i.e. Managing sails, lines & anchor).

•Must have a qualified First Mate who completes a Crew Resume for approval.

•Must present a valid US driver’s license, or International Passport to verify identity and DOB.

•We reserve the right to approve your application on the condition of having a Check-Out Captain aboard for the first day (or more) at your expense, which would be agreed to in advance as a condition of approval.

•For applicants under the age of 30 or over 74 additional crew requirements may apply.

Don’t be discouraged if your experience isn’t quite strong enough yet. We offer several ways to assist charterers to meet the requirements. As well as being able to offer an ASA instructor accompany you on your bareboat charter so you can achieve your ASA Sailing Certifications , we can also arrange a one or two day refresher for an experienced mariner that might need to get familiar with some of the more advanced systems on newer boats, or just brush up on skills if it’s been awhile. These programs are very flexible and can be personalized to each charter guest.

Download our Captains Application: Captains Application for Sailing Vessels

First Mate’s Application for Sailing Vessels

For Power Vessels

During the charter check-in process, which takes approximately 2½ hours, you will receive a very comprehensive yacht systems orientation, inventory review, safety briefing, and a chart briefing of the cruising area to ensure you are comfortable with your float plan and the vessel. It is required that the Captain & First Mate arrive at the same time and attend the vessel check -in.

Optional Orientation cruise If you are chartering a manufacturer of boat for the first time and would like to do a short orientation sail to familiarize yourself with all the systems and equipment while under way, we highly recommend an orientation sail with a Captain familiar with your sailing vessel. It takes about an hour and they charge $150.00. This is an excellent way to do a shake down sail to make sure you can enjoy your vessel with confidence. This must be booked in advance to ensure there is a Captain available. This is not intended to teach boat handling skills.

[email protected] 305-934-5295

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Destination and charter fleet updates, special offers, and more

Captain Only Charters

Captain only charters your sailboat. your captain.

Meet your yacht at our home in Soper’s Hole

“Know your charter is going to be perfect, without any drama.”

Experience exhilarating Sailing and Nature.

“Discover the Islands of the Florida Keys.”

“Morning Star Charters.”

Let the day Start and stop when and where you desire.

“The Perfect Get-a-way”

“Enjoy the feeling of being welcomed into the Morning Star sailing family”

Sailing at it’s best

“Morning Star Charters is the longest established Sailing snorkeling Charter company in the Florida Keys.”

Enjoy self-prepared Meals from your well equipted galley while surrounded by incredible beauty

“All the water toys you could want, available to rent right here at Morning Star Charters.”

Morning Star Charters, Sailing, Snorkeling, Kayaking, Sunset Sails, Cottages and Sailboat Rentals in the Florida Keys / Key Largo. Sailing and land based Sailing Vacations.

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Florida Keys has 8 Photos

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Florida Keys Yacht Charter

Often considered America 's Caribbean Islands the Florida Keys yacht charter offers spectacular locations to explore.

You will often read references to a 'jade necklace' or a 'string of pearls' in descriptions of the many (800+) islands that stretch off into the sea. The Keys have become increasingly busy over the last few years with an increase in cruise ship and other tourism. The keys feature plenty of energy ashore, but to get away into the quieter areas a charter yacht is the only way to go.

Photos: 1. A diver explores the coral reef in the Florida Keys National Marine Sanctuary off Key Largo - The reef system in the Keys is the only contiguous coral barrier reef in North America - Photo by Bob Care-Florida Keys News Bureau; 2. A Florida Keys fishing guide positions his angler to cast for a bonefish off Key Largo- Photo by Bob Krist-Florida Keys News Bureau; 3. Sunset in Key Largo- Florida Keys- paints a pretty picture at the Kona Kai Resort -Photo by Bob Krist-Florida Keys News Bureau

The first Key to come across on your cruise south will be Key Largo . Over the years Key Largo has become a busy weekender retreat from the mainland. As you sail further down though the Keys you will finally come to the last one, Key West .

The Florida Keys are sheltered by the only living coral reef in the United States. The Keys are well known to yacht charterers for the spectacular scuba diving and snorkelling, kayaking and eco-tours, dolphin watching, island hoping and fishing.

The types of yacht charter available in the Florida Keys are all the main types including motor, sailing, bareboat charter, skippered, crewed yachts, catamaran, power boat, sailboat, luxury yachts and super yacht charter.

The Florida Keys features a year round calendar of special events such as fishing tournaments, international yacht races, motor yacht races, Fantasy Fest, a lighted boat parade and Florida's own 10 day long Mardi Gras. We recommend charter yachts with a draft of under 4 or 5 ft (1.3 - 1.5m), as with a catamaran, so that you can get in to all the best areas within the Florida Keys.

Key West Yacht Charter

Key West has the ideal year round climate for yacht charter. Key West is a very unique town being the southernmost US city where history and tradition meets natural beauty and serenity. This city has real estate titles that date back to the King of Spain! Within walking distance from the historic Seaport District you will find palm-lined streets, tropical gardens, Ernest Hemingway's home, fine shops, art galleries, quaint restaurants and cafes. You can walk in the footsteps of Thomas Edison, Lou Gehrig, Harry Truman, and Tennessee Williams. You will also discover lively bars and pubs along with street musicians, jugglers, mimes and artists.

It is not unusual for charter guests to day sail their charter yachts using Key West as a base. They will sail and explore the keys during the day, utilising the restful anchorages, and then return to the first class marinas at night to experience Key West's nighttime entertainment. Remember to radio ahead to reserve marina space, as Key West is a busy part of the Florida Keys.

Below is a selection of fabulous Florida Keys charter yachts - please, contact us for additional vessels and more information here .

• Florida Keys Charter Itinerary
• Browse Florida Keys Charter Yachts
• Luxury Motor Yachts for Charter in Florida Keys
• Luxury Sailing Yachts for Charter in Florida Keys
• Luxury Catamarans for Charter in Florida Keys
• Florida Keys Yacht News

Florida Keys Yacht Charter Enquiry

"I have just emailed your post charter feedback to you. It doesn't say nearly enough about how well and hard you worked on this deal. I am a retired commercial real estate broker who understands the importance of the deal-maker in the deal. You are a deal maker of the first order." E. G - chartered in Florida Keys.

Yachting Destinations Near the Florida Keys

In close proximity to the Florida Keys are a number of exciting sailing destination.

New England

Napa Valley

Yachts for charter in the florida keys, queen miri | from eur€ 1,125,000/wk.

KENSHO | From EUR€ 850,000/wk

WAYFINDER | From US$ 375,000/wk

STARSHIP 185' | From US$ 275,000/wk

MARIA | From US$ 230,000/wk

LADY ELAINE | From US$ 225,000/wk

GIGI | From US$ 225,000/wk

MYSORAH | From US$ 200,000/wk

ASPEN ALTERNATIVE | From US$ 199,000/wk

FAM | From US$ 195,000/wk

GLORY | From US$ 179,000/wk

ZOOM ZOOM ZOOM | From US$ 175,000/wk

AVALON | From US$ 155,000/wk

FOCUS | From US$ 150,000/wk

AQUASITION | From US$ 150,000/wk

RELENTLESS | From US$ 150,000/wk

CLAIRE | From US$ 139,500/wk

ICE 5 | From US$ 135,000/wk

PLAN A | From US$ 125,000/wk

Florida Yacht News

Charter 29m motor yacht SOL SHINE in ...

Luxury yacht INVICTUS available for ...

Florida charter yacht REAL SUMMERTIME ...

38m superyacht GLORY offering charters ...

Charter yacht disclaimer.

This document is not contractual. The yacht charters and their particulars displayed in the results above are displayed in good faith and whilst believed to be correct are not guaranteed. CharterWorld Limited does not warrant or assume any legal liability or responsibility for the accuracy, completeness, or usefulness of any information and/or images displayed. All information is subject to change without notice and is without warrantee. A professional CharterWorld yacht charter consultant will discuss each charter during your charter selection process. Starting prices are shown in a range of currencies for a one-week charter, unless otherwise marked. Exact pricing and other details will be confirmed on the particular charter contract. Just follow the "reserve this yacht charter" link for your chosen yacht charter or contact us and someone from the CharterWorld team will be in touch shortly.

Florida Keys

Some of the most unique vacation destinations in the world can be found in unexpected places – such as the Florida Keys. Located just off the coast of South Florida, these islands have a relaxed feeling, stunning tropical scenery, and exotic wildlife; yet they are all located a relatively short distance from cosmopolitan Miami and the excitement of South Beach, where the journey begins.

Sneak Preview

• Newfound Harbour

Miami is South Florida’s playground, and for good reason – there is no where like South Beach to both enjoy the sun, sand, and surf by day, and live it up by night in the area’s many exclusive night clubs and restaurants. Whether you want to dance all night and enjoy premium bottle service or simply have a wonderful meal by the water, launching in miami ensures that you will start your voyage off in the most exciting way possible.

Visiting during one of the many major annual events that occur in Miami (including Art Basel, the South Beach Wine & Food Festival, the Orange Bowl, and more) will make your trip even more outstanding.

As the northernmost and largest island in the Florida Keys, Elliot Key was once used a refuge for pirates and today it is home to Biscayne National Park, with its lush vegetation and amazing beaches that offer both remarkable solitude and spectacular vistas – along with a variety of exotic birds and butterflies. You can also explore the island by kayak – there are many hidden lagoons, mangrove-covered shorelines, and winding creeks to discover. What’s more, you can enjoy your own catch for dinner after a day of capturing fish, lobster, or crab.

Key Largo is considered the “Diving Capital of the World”, with plenty of scuba diving, snorkeling, and sport-fishing options for avid enthusiasts – what’s more, it is located near the Everglades, allowing for easy access for kayaking and eco-tourism as well. It is the home of the only living coral barrier reef in the continental United States, and enjoys more than three thousand hours of sunshine per year, making it perhaps the quintessential island vacation destination.

Named after the original settlers’ boat the “Island Home” and now nicknamed the “Village of the Islands”, Islamorada is home to many notable residents (including Major League Baseball players Ted Williams and Miguel Cabera as well as actor Gene Hackman), this is one of the more serene island destinations in the Florida Keys as well as one of the world’s premier fishing destinations. Luxury resorts, shops, and art galleries are part of the Islamorada scene, but there are plenty of beaches that offer more solitude.

With less than two hundred residents, Duck Key is perhaps the closest version of a deserted island that’s still easily accessible from the contiguous U.S.  With world class fishing and sandy beaches, the island is also home to a luxurious spa and offers the opportunity for visitors to swim with dolphins.

Newfound Harbour not only offers spectacular scenery, it is home to the Florida Keys Sanctuary preservation area, which is partially located within the Coupon Bight Aquatic Preserve. The amazing sea life that visitors to the island will enjoy includes star corals and giant brain corals – perfect for amateur or inexperienced divers since these are located within in depths of 18 feet or less. Angelfish, butterflyfish, surgeonfish, damsels, wrasses, grunts, snappers, and parrotfish swim alongside the occasional grouper, along with many other types of fish that you’ll find colorful, striking, and unusual.

Along with some of the most interesting coral reefs in the world, Newfound Harbour is home to a sheltered tropical lagoon that serves as an oasis for a wide range of wildlife, including the tiny Florida Key deer, wading birds, and sea turtles.

Taking a little time to leave it all behind in Key West may be the ultimate form of relaxation – particularly if you happen to visit during one of the island’s most distinctive festivals (The annual Fantasy Fest held in October is the most famous). There’s excellent opportunities for scuba diving and snorkeling around the coral reefs and shipwrecks in the nearby waters, including the recently sunk USNS Gen. Hoyt S. Vandenberg, which created an artificial reef.

However, the island’s unique National Parks and wildlife refuges are perhaps the most interesting (at least for nature buffs), and the nightlife in general is not to be missed, with a variety of options that range from casual tropical dives to trendy nightclubs. All in all, Key West is the perfect culmination to your customized trip through the Florida Keys.

Sailing the Florida Keys may possibly be the very best way to unwind and explore a corner of the United States that hardly resembles anywhere else in the country – or the world, for that matter. And there’s no better way to experience this special part of the world than on your own private yacht.

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Private Yacht Charter – Dinner Cruises to Multi-Day Boat Trips

The Motor Yacht Somerset is a fully restored 58′ 1971 Trumpy Cruiser, available now for your next yacht charter. Somerset was restored to concours level in 2013, and is ready to charter in Florida, The Florida keys, and the Bahamas, as well as for member use at the Ocean Reef Club. Ideal for sunset cocktail cruises, dinner parties, and island-hopping vacations, Somerset is the perfect vessel to host your family and friends in classic style and comfort.

The Motor Yacht Somerset

The Motor Yacht Somerset has been completely rebuilt from the ground up. The refit has included a new bottom, keel frames and floors, rebuilt engines, new generators and systems, an entirely new interior and new paint. Somerset is basically a brand new Trumpy Yacht after this restoration. The interior pays homage to the quality and style synonymous with the Trumpy Name.

• Accommodation
• Description
• Specifications

The aft master cabin features a queen size center-line berth, the guest stateroom offers a full queen and the forward crew quarters sleep two additional in over-under bunks. Two spacious, tiled aft heads (the master cabin head is ensuite), both with separate stall showers. Forward of the master and guest cabins is the completely new galley.

The galley is equipped with a stainless sink, Miele 4-burner cooktop/oven and Vitrofrigo refrigeration system with Isotherm freezer. Built-in washer/dryer. New furnishings have been custom designed and made for the boat. The vessel is heated with a reverse cycle heating system and is air conditioned. Somerset’s interior is finished with the original butternut paneling in the main salon as well as teak in the wheelhouse, aft deck and galley. Her sole is cork.

Private Boat Trip on Somerset

From day trips, half-day trips, and sunset cruises, to overnight trips through the Bahamas or along the Florida Keys, you can book a private yacht charter with our captain and chef and receive everything you need for a relaxing and luxurious time on the water. Browse our yacht charter packages and book today, or contact us for custom charter options.

Book Your Private Yacht Charter

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