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!
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Friends of SSKW
Legal & safety.
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, 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:
- 12 boat rentals in Key West, FL
- 12 boat rentals in Stock Island, FL
- 12 boat rentals in Key Haven, FL
- 12 boat rentals in East Rockland Key, FL
- 12 boat rentals in Cudjoe Key, FL
- 12 boat rentals in Summerland Key, FL
- 12 boat rentals in Little Torch Key, FL
- 12 boat rentals in Big Pine Key, FL
- 9 boat rentals in Marathon, FL
- 9 boat rentals in Key Colony Beach, FL
Key West, FL could be the ideal yachting playground for you
Top private boat rentals inventory 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, can i pay in installments for my sailo boat rental, sustainable yachting tips.
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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.
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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