Half-Day Sail

4-5 Hours
Lunch Included: Deli Sandwich, Salad or Fruit/Cheese Tray Water, Sodas, Juice or Sports Drinks (BYOB)
Sanitized Snorkel Gear Included
Towels Provided
Captain & First Mate Provided
Six Persons Maximum
Learn Sailing Techniques, Take The Helm, Pull Up Sails Or Just Relax
See Dolphins, Turtles, Sea Gulls, Migration Birds, Reef Fish And More
Gratuities Appreciated

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.

Full Day Sail

7-8 Hours
Lunch Included: Deli Sandwich, Salad or Fruit/Cheese Tray Water, Sodas, Juice or Sports Drinks (BYOB)
Sanitized Snorkel Gear Included
Towels Provided
Captain & First Mate Provided
Six Persons Maximum
Learn Sailing Techniques, Take The Helm, Pull Up Sails Or Just Relax
See Dolphins, Turtles, Sea Gulls, Migration Birds, Reef Fish And More
Introduction To Learning How To Sail
Fishing With Florida Temporary License
Visit More Reefs
Lunch & Fruit Tray
Sail The Whole Day

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.

Sailing Charter Packages

A unique way to enjoy Key West!

Choose from our 3 sailboats in the Historic Seaport.

Blend the Key West Experience with Sailing/Snorkeling
Sailing Is Included With Every Charter
Choose The Sailing Charter You Wish
“Live Like A Local” - Mix Your Charter Choices
You Are In Charge Of Your Schedule
Working Facilities On Board
The Excitement Of What Key West Has To Offer
Barrier Reef Just 7 Miles Out Waiting For You
Three Boats Available
Gratuities Appreciated

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.

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

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.

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.

Overnight Excursions at Anchor

24 Hour Increments With Captain & Mate
All Meals Provided
Tell Crew What You Want To Experience
Snorkel Reefs
Play On Beaches
Fish The Edge Of The Gulf Stream
Anchor In Nature’s Beauty For The Night
Dinner Under The Stars
Breakfast Watch The Sunrise Or Sleep In
Two Private Cabins & Two Heads/Bathrooms
Salon Couches If Needed For Family
Gratuities Appreciated

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:

Your sailing as a willing crew, pulling up sails, and taking the helm.
Or you can kick back and soak up the rays, read a book on the deck.
Snorkeling the barrier reef with several reefs to choose from.
Atlantic side for colorful fish and great array of corals.
Enjoy Gulf of Mexico with a variety of choices including:
- a dolphin playground
- Cottrell Key with underwater caverns usually housing sleeping sharks and rays.
- Longer sails in the Gulf with Sand bars for Barbeques
Sail Hawk Channel in light waves & fresh breezes, wave-protected by reef.
Anchor in a lagoon near an uninhabited island or park.
Beaching on a natural crescent shaped beach with sand bar.
Stop over at Bahia Honda State Park and enjoy award winning beach.
Snorkel a 200 foot long ahip-wreck in shallow water!
Fish off the edge of the Gulf Stream with our gear!
Explore currents, creeks, and rivers between islands and mangroves.
Enjoy world famous sunsets from the deck of your boat, Star gaze.

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.

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