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Key West, FL

boating guide

In addition to the best offers we have for boat and yacht charters in Key West, FL, see also options available for rent in these nearby locations:

• 25 boat rentals in Key West, FL
• 25 boat rentals in Stock Island, FL
• 25 boat rentals in Key Haven, FL
• 25 boat rentals in Cudjoe Key, FL
• 25 boat rentals in Summerland Key, FL
• 25 boat rentals in Little Torch Key, FL
• 25 boat rentals in Big Pine Key, FL
• 10 boat rentals in Marathon, FL
• 10 boat rentals in Key Colony Beach, FL
• 10 boat rentals in Duck Key, FL

Discover Key West, FL with Sailo - a gorgeous boating playground for you to enjoy!

Ready to see your options for renting a sailboat in key west, fl, learn how to find the perfect yacht for you, how much is it to charter a key west, fl yacht for a day, what is sailo’s cancellation policy, sustainable yachting tips.

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How to rent a sailboat in florida keys, find the perfect boat.

Enter your desired location and date to explore our fleet of sailboats.

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Connect with your boat owner and complete your booking online.

Enjoy your day on the water with friends and family!

Why Boatsetter?

As the global leader in peer-to-peer boat rentals, Boatsetter offers an easy, safe and accessible way to experience on-the-water adventure. With boat rentals in 600+ locations, finding a boat is easy and with the option to tap into the largest network of USCG licensed captains, boating experience is not required.

Get out on the water worry-free, knowing our insurance covers every boating trip

Choosing the right boat rental platform is essential to your peace of mind while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

Got questions?

Frequently asked questions

What makes Boatsetter different from other boat rental platforms?

What makes Boatsetter different is peace of mind. Boatsetter is the first and only boat rental marketplace to offer insurance on every peer-to-peer boat rental. We know choosing the right boat rental platform is essential to your experience while on the water. That's why we've gone the extra mile to focus on safety through our exclusive partnership with GEICO Marine and BoatUS. As the first and only boat rental marketplace to offer insurance on every peer-to-peer rental, you are protected during all rentals with insurance coverage and on-water assistance through TowBoatUS.

How to rent a boat on Boatsetter?

At Boatsetter, our mission is to make getting out on the water as easy as possible. With our intuitive booking system, you can rent a boat as soon as today. -First, you must determine your budget and the type of boat you want to rent. -Next, decide where you would like to boat and the kind of boat you would like to spend the day on. -Finally, determine if you will be needing a boat captain and reach out to the boat owner. That’s it! You’re officially on your way to a fantastic day out on the water.

How much does it cost to rent a boat?

The cost to rent a boat depends on whether you are renting for a half-day or a full day, the boat features and the boat size can impact your boat rental price. Rental prices can range from $200 to $1,000 plus depending on the boat rental itself and the length of time of the rental.

How many people can fit on the boat rental?

The number of people who can fit on boat rental largely depends on the boat’s size and how many life jackets are on board. Currently the coast guard allows a maximum of 10-12 people on a Boatsetter boat rental.

How much does it cost to rent a yacht?

The cost of renting a yacht depends on the boat’s size and the amount of time you’ll use the yacht. The onboard amenities and luxurious accommodations also dictate the price. You can contact our yacht specialists for a custom quote by visiting https://www.boatsetter.com/luxury-yacht-charters .

How old do you have to be to rent a boat?

You must be 18 years old to rent a captained boat and 25 years old if you would like to rent a bareboat charter.

Do I need a boating license to rent a boat?

Boating license requirements vary from state to state. As a renter, you are responsible for understanding local state requirements.

Can you rent a yacht for the day?

Boatsetter allows you to rent a yacht for the day. Single-day yacht rentals are available for a select number of yachts. To chat with a yacht specialist please visit https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the week?

Boatsetter allows its customers to rent a yacht for the week. Renting a yacht for a week gives you more access to the wide range of yachts available on our platform. You can either book a rental directly through the site or connect with one of our charter specialists to plan your trip here: https://www.boatsetter.com/luxury-yacht-charters .

Can you rent a yacht for the month?

Booking a month-long yacht rental is a detailed and hands-off process when working with our team of yacht charter specialists. We tailor each yacht charter to our client's specific wants and needs. Our luxury yacht charter specialists can be reached at (954) 715-4114 or by visiting https://www.boatsetter.com/luxury-yacht-charters .

How to rent a private yacht?

Renting a private yacht is a very detailed experience that caters to your exact needs while onboard one of our luxury yachts. To plan your private yacht rentals experience please visit https://www.boatsetter.com/luxury-yacht-charters .

How much does it cost to rent a pontoon boat?

The cost of renting a pontoon boat depends on the size, location, and rental time of the boat. Prices can range anywhere from $200 for a half-day rental or just under a $1,000 for longer rentals.

How much does it cost to charter a yacht?

The cost to charter a yacht varies depending on the boat size and the length of the charter. Prices typically range from less than $1,000 to $5,000 plus if you’re wanting to charter the yacht overnight.

How much does it cost to rent a boat for the day?

The cost of renting a boat for the day on average ranges from $200 to $1200. The cost to rent a boat varies depending on the size of the boat and the length of time that you will be using the boat.

How does the boat insurance work?

Boat insurance typically covers loss caused by things such as fire, sinking, storms, and collisions. The extent of the coverage varies depending on the policy.

Do I need my own insurance to rent a boat?

You do not need boat insurance when renting with Boatsetter. Coverage is provided under the Peer-to-Peer Boat Rental Policy, which is underwritten by GEICO Marine Insurance Company. The policy was written from the ground up as a stand-alone recreational boat rental insurance policy covering the period of time that the boat is being rented and is available for all non-commercially insured boats.

Does Boatsetter screen renters?

Yes. We use a system called Cognito to ensure that payment information matches the renter's identity. We also require renters taking out a captained boat to be at least 18 years old and on a bareboat to be at least 25 years old.

Is listing my boat on Boatsetter free?

Yes! Listing a boat is completely free. We only take a commission when your boat is rented. We only make money when you do!

What if I'm not comfortable having a renter drive my boat?

If you are not comfortable having a renter drive your boat, we have an expansive network of licensed and experienced captains. Once your boat is listed, you can filter through our network of captains and favorite captains in your area that you would like to operate your boat.

Top destinations for sailboat rentals

Top sailboat rentals reviews in Florida Keys, FL

Luxury Sailing...

Amazing experience all around!

Set Sail on a 22'...

We had a great time on the boat! Beautiful day, beautiful weather, nice boat!

We had a great time. Aaron was a wonderful captain. Highly recommend.

Aaron was awesome! We had a great day on the water. The boat was in great shape and Aaron took care of everything we...

Paul, Chris, Lime Key Boat Rentals and Boatsetter were AWESOME!

I own a well equipped C-22, and the one I rented...

Explore the...

Perfect boat. Great crew. Truly excellent experience!

The staff were great and provided a fun atmosphere. The boat was amazing, very clean and comfortable. Thank you, Juan.

Aaron was so nice and amazing! My husband and I just got married that morning and we wanted to do a sunset sail with...

Florida Keys...

Thanks Capt. John! Your boat was a beauty and we appreciate all the individual attention you and Tina provided me...

Such a beautiful classic sail boat!

Sailing Cataraman...

Serge was an amazing captain and helped us coordinate with our friends on a different boat to celebrate together....

Excellent service!!! Amazing boat!!

Sailboat Rentals in Florida Keys, FL

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 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.  

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.

Friends of SSKW

Legal & safety.

Welcome to our unique little hideaway. Secluded, serene, and perfectly located, our self-contained cottages have everything you need for a relaxing waterfront vacation.

There are no hidden charges – your stay includes:.

• Unlimited private sailboat use
• Snorkeling equipment
• Stand-up paddle boards
• Fishing gear
• Use of BBQ grills
• Onsite parking

In the evening, just walk or paddle around to local dining and dancing. Or stay on site and enjoy Key Largo’s incredible sunsets from one of the area’s most intimate settings… the Key Lime Sailing Club & Cottages. Easy to reach, hard to forget!

This was my 10th year of staying at KLSC in early March – it continues to be my vacation site of choice – and I’m already in the book or 2016. Great location, amenities and staff. It doesn’t get any better than this.

We had the most wonderful vacation. I want to thank you and your staff. It felt like everyone went out of their way to see our vacation was more then we expected. And it was. If anyone ask me where to go on vacation I only have one answer, “The Key Lime Sailing Club!”

Totally enjoyed our trip,staff was great, my wife had never sailed. She is hooked now, will be back soon, thank you for a great vacation.

Can’t say enough about the staff, perfect! Enjoyed all the watercraft available for use, kids loved the place:) Really enjoyed our stay, Talofa was great, the people and staff really made the trip awesome!

We had an amazing vacation at the Key Lime Club and so much fun sailing in the Keys! The staff were MORE than helpful and so fun to talk with. Loved the relaxed atmosphere, the family feeling at the tiki, and being able to use the water toys was a big plus. Give our love to Captain G, Irene, James and CJ! And thanks again for the sunset sail and the hospitality! We’ll surely recommend the Key Lime Club to others:)

We had a fantastic time. All of the water equipment was awesome! It was so nice not to have to worry about bringing all of that stuff with us. Our home was also equipped with tons of movies and games. What an excellent option for a family to have. Thank you KLSC!

We had a great time at KLSC. The staff was especially wonderful and attentive! We loved it there.

Sailing was great and your staff was very accommodating and top notch.Hello to Capt. G, Irene and Jeff

Perfect for our family vacation. Not over commercialized and a great place to get outside and discover things! Out boys loved it.

We were so pleasantly surprised at Key Lime North! Breathtaking, beautiful, and very hard to leave! Sandra, Nick, and Heather were wonderful, helpful, and will be our lifetime friends. Paulie made everything special including remembering birthdays and beyond! Captain Sheldon was a fantastic sailing instructor. Nothing beats this vacation!

We LOVED our stay and your hospitality. Everyone went above and beyond to make the stay enjoyable, including John from Michigan who took us out in his sailboat one afternoon. That was definitely our treasure of the week, spending time visiting with him while sailing. Diamond in the rough, so glad we stayed! Definitely would book here again if the Keys were our destination.

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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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One contact - every option - advice you can trust.

• Matching any competitive offer
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• 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.

• 305-619-0140

BAREBOAT Charters

Come enjoy our islands in paradise, 3 day / 2 night packages.

Sailing Vacations are so easy with us in the Florida Keys!  The best destinations are in our backyard. 

You can sail, snorkel & explore. Dine aboard under the stars…or ashore at our island’s favorite Tiki Huts.

Sailing in the Florida Keys has never been so easy and affordable.

* Includes FREE Dockage with COOL A/C* * Fuels not Included * *Daily Snorkel Gear Rentals * * Longer stays are available at the same rates per each additional day*

JADE PACKAGE

Catalina 27' - "jade".

She is great weekend/day charter boat.  She includes a n ice-box; Roller furler; Bimini; Sleeping for 4; Swim platform; Lazy jacks; PFDs.

SALINA PACKAGE

Catalina 30' - "Salina"

Main & Roller Furled Jib; Tiller, Inboard Diesel; Galley w / Ice Box;  Head ; VHF; GPS; PFD’s; Compass; Bimini; Swim Ladder; USCG Equipment; Chart & Anchor – 4′ 6″ Fixed Keel.

Limit 4 aboard

SERENDIPITY PACKAGE

Irwin 34 - "serendipity".

Main & Roller; Furled Jib; Air Conditioning; Wheel Steering; Inboard Diesel; Water; Galley w / Ice Box;Head; VHF; GPS; Swim Ladder; Compass; Bimini; USCG Equipment; Chart & Anchor – 4′; Fixed Keel

SAYONARA PACKAGE

Beneteau 51 Oceanis - "Sayonara"

This vessel spares little when it comes to accommodations: 4 stateroom cabins with separate head/showers. She boasts 2 onboard A/C units; generator, ice maker, entertainment center, hot/cold water, wine cooler, swim platform, full galley, etc. 

Call for Pricing

Information.

• In the event of any weather cancellation determined by the customer or Florida Keys Sailing a “rain check” may be given. Sorry No Refunds.
• No SCUBA tanks.
• No smoking or vaping while on board.
• Bareboat Charters begin 9AM on Day 1 and end 5PM on Day 3. 3 Days and 2 Nights w / dockage at Keys Fishery & Marina is included.
• If staying aboard the night before. Check in time is:  4PM to 5PM. Sorry… no later arrivals.
• We require Tow Boat US Insurance or Seatow insurance memberships. No charter may begin prior to having that membership ID. 
• Navigation Limits are 50 NM from our sailing location. This includes sailing to Key West, FL.
• All boats need to be taken from and returned to: Keys Fishery & Marina 35th St. Gulfside Marathon, FL.
• Federal and State Laws require a proper checkout of all vessels, including the completion of Bareboat Agreement.

• 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

½ - Full Day Sail, Snorkel, Kayak, Sunsets

2 to 6 individual passengers or single groups up to 12. Laid back relaxed fun atmosphere. Enjoy our Captained sailing/ snorkeling or sunset Sails, both Bayside & Oceanside. Let 30 years of experience on the reefs and waters around Key Largo set you free to discover. Enjoy the beauty of the Florida Keys.

Captain Only Charters

Included is a luxury, well-equipped catamaran or monohull with an experienced and professional Captain in charge of the boat and helm. Sit back with a chilled cocktail and experience an unforgettable dream vacation in the beautiful Florida Keys.

Bareboat Charters

Included Catalina 22’ to a performance ORA design 36’ C&C or Gemini 34’ catamaran, our boats are well-equipped for their chosen usage. Enjoy the freedom of a self-captained vacation. Explore and enjoy sailing in calm, turquoise waters of the Florida Keys.

Own-er-ship in the Florida Keys. What are the benefits:  Tropical, US Waters, 1000’s of miles of shore line, Second Largest Coral Reef in the world, Quick & Easy Access.

Learn to Sail

Learn to Sail or advance your sailing in The Florida Keys. We have an in-house sailing endorsement that teaches you to sail a 22 ft Catalina 22 sailboat or we have the advanced ASA classes from Learn to sail ASA 101 to ASA 120. Why sail in the Florida Keys?

Cottage & Sailboat

Enjoy the beauty of the Florida Keys. Accommodations + Free Sailboats, Kayaks, Canoes, Paddle boards, Fishing/Snorkeling gear and more. All included in a Laid back relaxed fun atmosphere. On the Bayside of Key Largo. Let years of experience around Key Largo Florida set you on a path of discover.

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

Our Sailboats

If you’re an experienced sailor we invite you to use one of our own 22′ sailboats with your cottage rental at no additional charge. there’s no better way to relax and enjoy the keys.

Our 22 foot Catalina or O’Day single-masted sailboats are perfect for cruising the calm waters of Florida Bay. Just grab your cooler, walk to our dock, and point the bow into the horizon. Explore the Florida Keys in style! Leave and return when you like…after all, you don’t want to be tied to any schedule when you’re on vacation.

And if sailing isn’t for you, try our kayaks, canoes, standup paddle boards, rowboats, or even one of the floats we make available to our guests at the dock. The point is: take to the water! It’s the Florida Keys way of life!

Even relatively new sailors can enjoy the Bay on one of our easy-handling day cruisers. It’s great family fun, and a big part of the reason Key Largo Cottages remains so popular with our guests. Find out for yourself!

22′ SAILBOAT RENTALS

Rent a 22’ Catalina Sailboat and sail around the beautiful Key Largo bay area for only $300/day plus taxes. Note: We mainly rent the cottages with a free sailboat but on a case to case basis we may have an extra sailboat that we can rent out. Just call when you are in town and we will see if we can help you get your sailing needs taken care of.

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 5 day/4 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.

6651 Maloney Ave, Unit 1 Key West, FL 33040

[email protected] 800-650-6940

KEEP IN TOUCH

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How to Find Affordable Sailboat Rentals in the Florida Keys

January 9, 2019

Know Your Budget

Figure out where you’re staying, take online learning before the trip, compare different rental providers in the area, bring a friend with you, take advantage of current promotions, book far in advance.

Welcome to the Florida Keys

Welcome relax at a florida keys weekly vacation rental that includes a sailboat with your stay….

 Our Florida Keys waterfront accommodation with a sailboat is an ideal place to stay for the experienced sailor, avid fisherman and anyone who wants to enjoy a great vacation experience in the Middle Keys.We offer a clean, comfortable, affordable vacation rental in the middle Florida Keys, 10 miles north of Marathon on Conch Key.

Conch Key is a small island with 50 homes. It is reminiscent of a tiny old Bahamian lobster fishing village, with colorful tropical painted houses and charmingly cluttered lobster traps, nets, and fishing gear.

Accommodations

 waterfront accommodation.

“CONCHED OUT” is our 2 bedroom house, each with a Queen size bed. This unit will accommodate 4 people.

You can easily do a day trip to Key West or Everglades National Park

Our ideal location, the middle Keys, will allow you to venture out in either direction. You can easily do a day trip to Key West or Everglades National Park .

Key Largo is very famous for their John Pennecamp State Park which has beautiful patches of coral reefs. Sombrero Reef , off of Marathon, is also another great place to snorkel or scuba dive.

Hawk’s Cay Resort, only 2 miles down the road, offers scuba divers reef trips, with equipment. There are also numerous dive shops available in the area. For you snorkelers, we offer a small selection of “complimentary” snorkel gear.

Long Key State Park , which is 4 miles from our vacation rental units, is a great place for a walking tour of the old hammocks – the vegetation of the Florida Keys before development. There are lots of shorebirds, songbirds, and waterfowl; plus, many species of native palms and hardwoods. At this state park you can also rent canoes and explore the natural mangrove channels.

At our Florida Keys rental with sailboats , you have the use of our kayaks and bicycles – or just sit under the coconut trees with one of our good books from our library. Enjoy a Florida Keys romantic sunset from our dock, be sure to look for the “green flash”.

Reservations

Availability & pricing.

To request a reservation at conchkeysailboat, simply complete this form and click “Submit”. We’ll contact you as soon as possible to confirm the availability and finalize your reservation.

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30 S Conch Ave, Marathon, FL 33050, USA

+1 305-340-9578

[email protected]

We are located on the island of Conch Key, mile marker 63, just past the Long Key Bridge. This bridge is approximately 2.4 miles. You will find the mile markers (small green signs) along the side of US 1. Key Largo is mile marker 120 and Key West is mile marker 0. Conch Key is on the bayside of U.S. 1.

We’re very proud of our reputation. Our vacation rental units are very clean and comfortable. Upon check-in you will notice colorful hibiscus flowers and conch shells scattered around the walkways and inside the rental unit.

Call for an appointment to tour the facility and visit with us.

Call +1 305-340-9578

Or email us at: [email protected]

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Our charter advisors are here to assist you.

An expert will find you the best offers

The state of Florida in the United States is home to some of the most popular boating destinations and cities such as Miami and Fort Lauderdale. While these areas offer many boats, Miami and the Florida Keys have some beautiful sailing conditions, which makes sailboat rental in Florida particularly popular.

Pricing and Info on renting a sailboat in Florida.

To rent a sailboat in Florida, prices cost around £500 for the day, while renting a sailboat in Florida for a week will average at around £4000. These prices vary however, due to the type of boat and the time of year you want to go.

Sailboat availability in Florida

Because Florida is sunny year-round, it does not follow the conventional sailing season. The peak season will typically run from December deep into February, but sailing still goes strong into May. If you’re looking to avoid the influx of tourists, then sailing in the months of April and May is perfect for you. Outside of this period, you’ll still have plenty of sunshine, but you’ll also have heavier periods of rain and humidity. Even in the low season sailing is very popular in Florida, and so you should always book far in advance.

Do I need a license to rent a sailboat in Florida?

To rent a sailboat in Florida, you do not need a license, however, if you were born on or after January 1st of 1988 you will need to obtain a Boating Safety Education Identification Card, which will require you to complete an approved Boating Safety Course. Also, if you are 18 years old or younger, you cannot rent any sort of watercraft.

If you do not have a licence or sailing experience, you can rent any of our sailboats with a skipper from our catalogue. When you rent a skippered sailboat, you can relax and enjoy your trip. The skippers help you to get to know the places you visit by boat in depth.

Overview of Florida

Undoubtedly one of the best areas to sail in the USA is Florida. With the sunshine year-round, you’ll always have perfect conditions to explore this beautiful state by boat. Due to its geographical position, it’s a sailor's paradise with an endless coastline that is available. If you’re living in the US, it’s the perfect place close to home; if you live abroad, it is more than recommended to make the trip.

In Florida, you’ll have several options for where to rent a boat. One of the most popular destinations to sail in Florida is the Florida Keys. Rent a boat in Key West, here you will have access to some of the best island hopping and you will be able to create a unique journey. Seeing the different islands and several coves is a highlight of any vacation. If you plan on sailing in the Florida Keys, chartering a yacht for at least is the right way to go.

Besides the Florida Keys, you’ll also be able to rent a boat in Fort Lauderdale. Fort Lauderdale is the perfect departure point for seeing the coast of Florida. Because of its location, you’ll have access to hot spots like Miami or sail down to the Florida Keys. Either way, you’ll surely have the perfect sailing holiday in Florida.

Due to the popularity of sailing in Florida, it is no wonder sailboat rental is so popular, as the sailing conditions are some of the bests you will find in the US, particularly in the Bay of Florida, with Miami and the Florida Keys, in particular, being a popular area to rent a sailboat.

Sailing areas around Florida:

• Florida Keys
• Fort Lauderdale

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At Blue Skies Charters, we have a passion for the open sea, redefining sailing experiences and offering first-rate, unparalleled services to our customers. Our fleet of luxurious high-performance vessels sets us apart from other run-of-the-mill boat charter companies, ensuring that each voyage lets you discover the beauty of pristine waters, idyllic coves, and beaches and experience the ultimate sailing thrill. From sunset cruises to private island vacations, we enable you to navigate your nautical dreams and transform them into realities.--> Florida Keys with Blue Skies Charters.-->