Key West Sailing Adventure

Private Sailing Charters

305.304.4911

info@keywestsailingadventure.com

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Exclusive Private Sailing Charters For Small Groups!

Wild Thing port side salon to vbirth 2014 Wild Thing port side salon to vbirth 2014 Wild Thing port side salon to vbirth 2014 Wild Thing port side salon to vbirth 2014 Wild Thing port side salon to vbirth 2014
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Wild Thing under sail during sailboat race Wild Thing under sail during sailboat race Wild Thing under sail during sailboat race Wild Thing under sail during sailboat race Wild Thing under sail during sailboat race

Half-Day Sail

Sail to the Barrier reef 7 nautical miles out from Key West. We have all the snorkel gear you will need. Your captain and mate will outfit you. Sail to the reef through an amazing ever-changing array of aquatic colors. The reef has many choice spots. We know most of them, meet the fish, see the reef, and find a color you have never seen before, up to 6 persons.

Book online now!

Sunset Sailing Charter

Treat yourself to your own private two hour sunset sailing charter for up to six people. Customize your experience to enjoy one of the most famous sunsets in the world. Great for special occasions like anniversaries, proposals, or birthdays. Your crew, the captain and mate, will greet you at the dock about fifteen minutes before departure. A refreshing fruit tray along with an ice chest with cold water will be provided. If you would like to design your day your way, please feel free to call and let us know what kind of event you are celebrating.

Book online now!
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Full Day Sail

Same as above but with more fun! More exciting options for your vacation activity, additional reefs for you to snorkel, extra time sailing, or fishing. Design your day your way, up to 6 Persons.

Snacks, cold drinks, iced cooler, provided on above charters, BYOB.
Book online now!
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Boca Grande Beach Boca Grande Beach Boca Grande Beach Boca Grande Beach Boca Grande Beach

Sailing Charter Packages

A unique way to enjoy Key West!

Choose from our 3 sailboats in the Historic Seaport.

44’ Morgan sailboat “Wildthing”  known for its great smooth ride, comfort and sailing ability, a world class sailboat $310 per night for 2 guests… A romance or family vessel, 2 cabins, 2 bathrooms for privacy and a large living room, sunny on deck.

Book Wild Thing Now!

42’ “St. Vitus Dance”  This sailboat is originally from the set of Miami Vice, it is now the newest member of our fleet.

Book St. Vitus Dance

37’ O’Day sailboat “Obsession”  a tried and true boat, she sailed most of the Bahamas and to Mexico. 6’ 3” headroom well thought accommodations. A cabin, galley, bathroom and living room forward and a private cabin aft with a private entrance. 2 cabins 2 bathrooms. We use her to race in regattas for fun. $210 a night for 2 guests.

Book The Obsession!Now!

All vessels can accommodate 4 in cabins and 2 more on couches if desired. Extra guests are $45 PP per night.

All Stay-Sail Private Vacation Charter Packages will include sailing. Either a Half day, Full day, or Overnight at anchor adventure.

For guests seeking a multiple day package, choose a boat and any combination of charters from the above list.

Gratuity A normal tip of 15-20% of the sailing portion is appreciated.

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Key West Sampler

By far the best of both worlds at land and sea.

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Overnight Excursions at Anchor

  Enjoy it all! Each 24-hour adventure will take you to the best locations for natural beauty. See reefs, beaches, lagoons and uninhabited islands. Snorkeling, fishing, or sunbathing. All meals are included and dinner is prepared for you at sunset. Watch the colors of the setting sun transition from day to night, with a vibrant spectrum of orange, red, and lemon hues. The day wraps up with you in a quiet lagoon for a night under the stars. Sleep like a baby.

Sailing Excursion Getaway Options

Some suggestions that we offer depending on the wind and your whim! These are some of our favorite activities:

Choices depend on your wishes and the length of your stay, oh and don’t forget the Bahamas…

Add more time for a multi-day adventure or an excursion to the Bahamas.

Add 2 more persons to above charter.  The boats have 2 cabins, each with its own bathroom and a spacious living room. Ideal for 2 couples or a family. Children under 12 are free.

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Weddings & Special Events Charters

Sunset Weddings

Charter for up to 6 passengers plus captain and mate, same rate for any of our 3 boats. We provide it all; Flowers, Cake, Food array, Photos, just bring your marriage license.

Wedding/Honeymoon Combo

Sailing vacation for 2 nights and the better part of 3 days of memorable dining, sailing, and ceremony. A true Keys Wedding with the added enjoyment of extra time sailing, swimming, snorkeling, beaching, dining to celebrate your new life together.

Weddings Check Availability!More... Book online now!
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Premium Charter Package

Pull all the stoppers for the two of you and let us cater to you.

For 4 nights and the better part of 5 days, we will attend to every detail and provide first class service. Starting with a Limo Pick up at Key West Airport, Flowers, Cold Drinks, Food array with Fresh Fruit await you at your boat with a mate to welcome you. While sailing your meals have been chosen by you or guided by you at a gourmet level.

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