- 305-619-0140
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.
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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. Only $2,039 per student! And better yet…a second student enrolls for FREE!
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. Only $3,599 per student! And better yet…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
Bareboat Charters
Bareboat charters. your sailboat. your experience.
Sail Away to Tropical Paradise: Explore the Florida Keys on a Well-Equipped Sailing Vacation
Picture this: a gentle breeze brushes against your face as you navigate the calm, turquoise waters of the Florida Keys. You’re at the helm of a beautiful sailing vessel, equipped with all the amenities you need to make your sailing vacation unforgettable. Whether you choose the Catalina 22′ for a day sail or the Morgan 33′ Out Island for an overnight trip, you can rest assured that your boat is well-equipped for your chosen adventure.
As you board your boat, you feel a sense of excitement and freedom wash over you. You’re in charge of your vacation – you get to plot your course and sail into tropical paradise at your own pace. The warm sun beats down on you, and you can’t help but feel grateful for this opportunity to escape the stresses of everyday life.
If you’re planning a multiple night charter, you can provision at one of the local chain supermarkets and enjoy your fully-equipped galley at your leisure. Or, if you’re just renting for the day, you can grab a packed lunch and set off on your adventure.
The Florida Keys offer a plethora of activities for sailors of all levels. From visiting underwater or land-based state and national parks to local beach bars and restaurants, there’s something for everyone. Take a dip in the crystal-clear waters, explore the mangrove islands, or relax on a secluded beach – the choice is yours.
Whether you choose the Catalina 22′, the Morgan 33′ Out Island, or one of our catamarans, you can rest assured that your boat is well-equipped for your chosen adventure. So go ahead, captain your sailing vacation in the Florida Keys and create memories that will last a lifetime.
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 Getaway”
“Enjoy the feeling of being welcomed into the Morning Star sailing family”
Sailing at it’s best
“Morning Star Sailing Charters is the longest established Sailing snorkeling Charter company in the Florida Keys.”
Enjoy self-prepared meals from your well equipped 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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Sail the Florida Keys
- Location Guide
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
Bareboat Motor Boats
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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 jam-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.
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.
Key West Sailboat Charter Aboard the Tamboo
Our Fleet: the Tamboo
Bareboat charter ~ asa sailing courses*, ocean's edge marina key west, florida 2023 bali 42' sailing catamaran (bareboat only) 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
Introducing Vivo Per Lei 58 Leopard Catamaran flagship model Learn More
Creating unforgettable journeys on custom designed luxury catamarans learn more, luxury catamaran sailing charters tailored in every way to suit your needs learn more, key west and key largo locations sailing the beautiful florida keys, bahamas and beyond learn more, catamaran sailing charters half day, full day & overnight learn more, welcome to calypso sailing.
Calypso Sailing was established in 1988 in the beautiful Florida Keys. With locations in both Key Largo and Key West we specialize in luxury sailing vacations on a range of Leopard Catamarans, both bareboat and Captained. Our monohull sailing charters can take groups of 6 to 38 on day, sunset and overnight trips whilst not forgetting the iconic African Queen steamboat from the 1951 movie starring Humphrey Bogart and Katharine Hepburn which operates daily in Key Largo.
Our aim is taking care of all your cruising needs
- Iris --> Florida Keys with Blue Skies Charters.-->