Key West Sailing Adventure

Private Sailing Charters


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Jump ahead to our Weddings At Sea charters!

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
first mate amy key west sailing adventure private charters first mate amy key west sailing adventure private charters first mate amy key west sailing adventure private charters first mate amy key west sailing adventure private charters first mate amy key west sailing adventure private charters
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!

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!

Private Vacation 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’ Irwin sailboat “Moondance”  swift, solid ride in comfort. Great deck space for lounging, 14’ wide makes for lots of room below. Invites larger groups with 3 beds, 2 bathrooms and 2 couches if needed. $310 per night for 2 guests extra guests.

Book Moondance now!

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.

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

  • 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!
Book online now!

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. - $1400 for 2 persons

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…

Book online now!

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 $1700.00 for 4 persons. Children under 12 are free.

Special Events Charters

$1595 - Sunset Weddings 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.

$2945 – Wedding/Honeymoon Combo

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 Wedding Availability!Availabilities Book online now!

$6200 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.
Book online now!

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