Key West Sailing Adventure

Private Sailing Charters


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.

Sunset Sailing Charter

  • Two-Hour Sunset Charter
  • Captain & First Mate Provided
  • Six Persons Maximum
  • Ice Chest with Cold Water
  • Fruit Tray

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.

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.

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

Key West Sampler

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

  • Do It All! Two Nights In Key West, 24 Hours At Sea!
  • See Excursion For 24 Hours Adventure Details
  • Blend Land & Sea Experience
  • Gratuities Appreciated
  • Day 1 Arrive at the boat.
    • We will meet you at the dock and familiarize you with the boat.
    • If you have any questions or concerns please feel free to ask.
    • Also, we may know some great places to eat.
    • Tomorrow you sail but tonight feel free to explore the Key West night life.
  • Day 2 Get Ready to Sail.
    • Take a short walk to one of many great breakfast locations.
    • Return to the boat and prepare to depart.
    • Upon arrival, the crew and you will leave on a 24-hour sailing excursion.
    • Enjoy at-sea fun activities!
      • Sailing
      • Snorkeling at coral reefs
      • Beach-combing Uninhabited Islands
      • Fishing
      • ...and more!
    • Arrive at Anchorage
      • Dine under the stars.
  • Day 3 Return to the Dock
    • Arrive at the docks around 1 pm
    • Enjoy an afternoon and evening
  • Day 4 Check Out
    • Check out time is by noon.
    • We enjoyed having you!

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.


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.

  • The first night at the dock on the sailboat relax, you are on your own. Key West Downtown is at your feet. No car needed; pool, theater, music, beaches, dozens of restaurants all in Old Town by your boat. We leave you alone, that all changes at noon the second day.
  • The second day at noon the adventure begins. Your captain and mate arrive with the menu items you have chosen and you sail off to a memorable adventure for 72 hours. We do all the work unless you want to help set sails or steer.
  • After a brief conversation to revisit and ascertain your wishes and goals we will plan your sail accordingly. Discussing wind direction and the best that time of the year has to offer we sail off for 3 nights and 4 days. Every morning over breakfast you will tell us what you wish for that day. We have found even with the most detailed plan after our guests begin to relax choices may change. It is your boat during this time.
  • While you are sailing to the barrier reef for snorkeling and lunch, share with the crew what you would want to do from the captains presentation of choices for the day based on conditions- sailing, snorkeling, fishing, beaching, kayaking, or exploring. It is your boat to command.