Sunset Sails

This is the best way to explore the beautiful islands in the comfort and privacy of your own company.
We have many different sailing options, which is what sets our private charters apart from the rest! Depending on your availability, you can schedule a private trip reservation for a few hours in the afternoon, evening, or even the entire day. You have the freedom to choose when and where you want to go, and our crew will make it happen. Alternatively, you can let our captain choose the sail tour route and stops, which makes an exciting surprise for you and your guests! Sunset Sails are the most popular!


  • Private 2 Hour sail
  • Professional Local Captain
  • Cheese and Crackers
  • Choice of Beer or Wine.

Cost $350

Half / Full Day Sails

The private sailing charters at Sail Florida Adventure take place on our 45 or 41 foot sail boat. We offer half day private sails, with the option of extending your trip for even more adventure! Our boat comes fully equipped with snorkel gear and flotation devices, so you can dive into the cool waters and see the rarely visited coral reefs just below the surface. In addition, our crew will serve you beverages, fresh fruits, and cheeses for you to enjoy during your sail. Sail Florida Adventures hopes to make your sailing trip a moment to remember.


  • Private 4 Hour sail
  • Professional Local Captian
  • Sandwiches of Choice
  • Fruit Platter
  • Drinks and Cooler full of Ice

Cost $550


24 Hour Island Escape

24 Hour Overnight Island getaway starts off with meeting at the sail boat at 11:30 for a 12:30 Departure from Key West Harbour Marina. We take a approximate 4 Hour sail to Marquesas Key about 24 Miles West or some other local Island of Key West. We drop and go explore a uninhabited Island while the chef is making your Dinner. We return to the sail boat to a beautiful dinner made just for you. During the night your view of the will surely amaze you!! Wake up early for breakfast, get wet and off to sail back to home base about 4-5 hours based on the winds and weather.


  • Private 24 Hour Sail and Island
  • Professional Local Captain and First Mate
  • Breakfast / Lunch / Dinner
  • Snorkel at local Reef  or Kayaking at at Boca Grande Island
  • All Drinks and Cooler full of Ice
  • off Grid (No cell phones)

Cost $1300

Back Country Sand Bar / Island Escape

Sailing not your speed?  We have a 26 foot World Cat center console with twin 225 Yamaha's.  She is fast if time is essential.  We can get you to the reef in 15 to 20 min or local Sandbar to hang out.


  • 4 Hours on Power Cat
  • Local Guide (Captain)
  • Snorkle Gear
  • Flotation devices
  • Cooler Full of Drinks and Ice
  • Beach Chairs /  BBQ Grill / Table

Cost $ 600

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