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.
- Chesapeake Bay Itineraries
- Key West Itineraries
- Chesapeake Bay
- Virgin Islands
- St. Vincent & The Grenadines
- Browse our Fleet
- Meet Your Captains
- Charter Management
- Sailing Lessons
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.
Rent the best Key West yachts
- Yacht Rentals
- Florida Yacht Rentals
Our top yacht rentals
Stock Island, FL
The Happy Prince 53' Luxury Yacht Rental Key West Florida
40' Luxury Sailing Catamaran! Offering 4 hr, 8 hr, & 10 hr charters
Key West, FL
Luxurious Private Yacht Charter
Marathon, FL
48' Daytona Sport Fisher with Captain
Luxury 51' Power Catamaran! Offering day, overnight, & sunset charters
Fountaine Pajot Elba 45
Naval Air Station Key West, FL
66' Luxury Sports Fish Yacht Key Livin’!
48' SAILING CATAMARAN! Offering day, overnight & sunset charters
Pristine Luxury 62' Yacht! Offering day, overnight, & sunset charters
Charter a luxurious double decker catamaran style yacht
Luxury 46' Sailing Catamaran! Offers day, overnight, & sunset charters
Duet - 2023 Seawind 1260 - 3 cabin/2 bath
Leopard 44 sailing catamaran, 4 cabin/4 bathroom
Beautifully restored sailing ketch in Key West
Key West Sport Fishing
Classic 1939 John Alden Schooner Yacht
How to rent a yacht in key west, find the perfect boat.
Enter your desired location and date to explore our fleet of yachts.
Select a captain
Choose to drive yourself or select a USCG licensed captain.
Book with ease
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 yacht rentals
Top yacht rentals reviews in Key West, FL
The Happy Prince...
Very nice !! Beautiful boat Well maintained .Ryan was great captain with great local knowledge of the keys...
48' SAILING...
Fantastic!!!! Tim and the Captain went above and beyond.
Ryan was an excellent captain. Great attitude with keen local knowledge that made our day at Boca Grand a total success.
Pristine Luxury...
We had a great day with Captain Dan and Kristin. Our family of 8 (ages 1-60) enjoyed cruising, snorkeling, and...
Duet - 2023...
We had a group of 12 people (plus 2 captains) and fit very comfortably on the top/main part of the boat. It was...
40' Luxury...
Incredible boat! The best way to see a Key West sunset. Lots of room onboard, great table set up for gathering....
We had a great day - thanks to Tim for all the communication before our day - ordering provisions was a home run too!...
Both Brian and Patrick operated the boat and were outstanding hosts to our full family.
All of us were very...
We had great day. The boat was in good shape and Captain Dan was awesome.
Tim the owner, Daniel and Molly, the Captain and first mate all provided an easy and very pleasant charter...
We had a great experience with Captain Matt in Key West on 12/26. He ensured the boat was stocked with everything we...
Yacht Rentals in Key West, FL
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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
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