1. Sailing Charter On 37ft "Free Spirit" Cruising Monohull In Key West, Florida (With Captain Only)
  2. Sailing Charter On 37ft "Free Spirit" Cruising Monohull In Key West, Florida (With Captain Only)
  3. Sailing Charter On 37ft "Free Spirit" Cruising Monohull In Key West, Florida (With Captain Only)

Sailing Charter On 37ft "Free Spirit" Cruising Monohull In Key West, Florida (With Captain Only)

7 bookings

Enjoy sailing in Key West, Florida! Charter the 37 feet "Free Spirit" Lazy Jack Cruising Monohull for up to 6 people. Rate as low as $149 per hour (minimum of 4 hours). Rates: • Half day: $595 • Full day: $895 (With Captain Only) What You Can Expect: Sunrise Sail Key West’s first and only sunrise sailing experience! Whether you’re completing your night or starting off your day, come experience the tranquility and beauty of the Gulf of Mexico and the Florida Straits as new day dawn. Enjoy as the captain and mate set sail, shut off the engine and the sails fill with the wind. Take in the rich natural beauty of the Florida Keys back country as the turquoise waters brighten the day, countless species of land and sea birds take flight and the local fisherman makes their way out to sea for the day’s catch. Toast the sun as it lights up the towering Florida cumulus clouds with our complimentary virgin mimosas and gourmet tropical fruit platter. As with all our trips, for a drink with a little more experience please feel free to bring any adult beverage of your choice! Day Sail Our Day sails offer a great way to see Key West from the water! Experience the joy of setting sail and shutting off the engine as we sail you through the colorful waters that surround our beautiful Island, Sail through the internationally renowned live- aboard anchorage, past Mallory square and the old Customs House and out toward Fort Zachary Taylor. Sail around Sunset Key and take a look at the Key West’s most fantastic National wildlife preserve. We always have a chance to see dolphins, turtles and a countless variety of sea birds. Sit back and relax or take a turn at sailing the boat, this truly is Your trip! With over 15 years experience sailing and living in the Keys, our captains and crew provide you with the local knowledge of marine life, surrounding islands as well as stories of Key Wests rich and colorful history. Come sail with us in comfort and style. Sunset sails Sunset sails are the thing to do in Key West. Capture the magic of it all without being on a boat crowded with people. Sunset Sail Key West we strive to revive the romance and charm without the crowds. Our vessels only take 6 guests to ensure comfort and allow for a more friendly and customer oriented cruise. Sit back while the captain and mate raise the sails, shut off the engine and sail off into the sunset! Take the wheel or take in the sights as we sail you through a tour of Key West harbor, sail past the crowds at Mallory square and cross the line of the Gulf of Mexico to the Atlantic Ocean! Look seaward and dream of sailing far away, take in the sea stories of our crew and plan your next sail with Sunset Sail Key West. With frequent sailor discounts and custom sailing packages available, we cherish our return customers. What To Expect Onboard: The vessel "Free Spirit" is a 37' Ted Brewer - lazy jack - Schooner built in 1976. This vessel has a small head and cabin, a large cockpit and has a fun aqua lily pad for added water enjoyment. If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.

Captain is included.
A captain is provided by the listing owner to host and operate the trip.
6 guests
Cruising Monohull


Our goal is to offer a true sailing experience for locals and visitors alike aboard unique classic vessels. From inspiring newcomers and first-timers, to helping our community sailors hone their skills while serving as captain and crew, We are about sharing the love of sailing. Our captain discovered his love for sailing after going out on a Key West sunset sail at the age of 13. Upon disembarking he turned to his father and said "That's what I want to do with my life" He was referring to sailing, and he has lived true to that statement ever since. He started then as a volunteer on traditional schooners from Key West to Maine, and through hard work and dedication, driven by sheer passion for the sea he climbed his way up the ladder to make himself one of the youngest schooner Captains on the East Coast. He has sailed and commanded some of the oldest and most renowned classic schooners on the water including General Patton’s When and If, the flawlessly restored Fife schooner Adventuress and John Alden’s magnum opus, the Bermuda Race winner Malabar X. Bringing his experience back to Key West, with the help of friends and loved ones he founded the company with the desire to provide a fun, compelling, customer orientated sailing charter company.

Features & Details

  • Life jackets/required safety gear
  • Galley Stove & Oven
  • Air Conditioning
  • Cabin
  • Wheel steering
  • Inboard Engine
  • CD Player
  • Head
  • Furling Headsail
  • Furling Mainsail

Approximate Location

You’ll get directions for the exact departure location when you make a booking inquiry.

The boat's approximate location on a map

Cancellation Policy

Full refund up to 5 days prior.

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