Availability: Key West Sailing Adventures

Room type

Entire Obsession 37-foot sailboat Cabin

Max Occupancy: 4 guests (up to 3 children, 3 infants)

Entire Wild Thing 44-foot sailboat Cabin

Max Occupancy: 4 guests (up to 3 children, 3 infants)

Key West self-catering Sailboat near Duval Street

Airport nearby

Close to the airport, this sailboat is also near Schooner Western Union, Dante's Pool/Waterfall, Duval Street, and Mallory Square, Additional nearby points of interest include Ernest Hemingway Home and Museum.

Welcome Aboard

Key West Sailing Adventures will have a crew member waiting for you at your boat for instrutions and set a sailing schedule, at the Historic Seaport Other amenities include a coffee shop/café and laundry,


In the center of both boats have a large living room, w/kitchen, cooking utensils, air conditioning, and refrigerators; rooms also include coffee/tea makers and CD players.

Key West Sailing Adventures Amenities


Key West Sailing Adventures features a Historic Seaport Marina, a coffee shop/café, and laundry,extra shower facilities. This Key West property the privacy most "Yacht Owners Enjoy" We are located in a prime location in Olde Town, walking distance to most activities. Rent bicyles or scooters, Electric cars and see the Island lazy-Like. Sunset celebration is a favorite event 3 blocks away off Duval St. Dante's swimming Pool is a hop away; food and cocktails. br/ br/ Your stay includes sailing and snorkeling ( gear on board) on a 3 day stay or just a laid back sunset on a 2 day stay.

  • Airport transportation (complimentary)
  • Coffee shop or café
  • Number of floors - 1
  • Tours/ticket assistance
  • Laundry facilities
  • Marina on site
  • Total number of rooms - 2
  • Self parking (surcharge)
  • Wedding services
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Self parking (surcharge)

Room Amenities
  • Separate sitting area
  • Climate control
  • Air conditioning
  • Coffee/tea maker
  • Complimentary bottled water
  • Housekeeping - once per stay
  • Second bathroom
  • Hair dryer (on request)
  • Complimentary toiletries
  • Desk
  • Sofa bed
  • Kitchen
  • Separate dining area
  • Private bathroom
  • Refrigerator
  • Shower only
  • Individually furnished
  • Individually decorated
  • Sofa bed size
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What sets us apart from the rest of the normal, is that; your (room) boat goes sailing depending on the package you choose. The Capt and Mate take you out to the reef for sailing and snorkeling ( gear on board) on a 3 day stay or just a laid back sunset on a 2 day stay.

  • Golfing nearby
  • Snorkeling nearby
  • Kayaking nearby
  • Sailing nearby
  • Scuba diving nearby
  • Windsurfing nearby
  • Scooter/moped rentals nearby
  • Bicycle rentals nearby
  • Hiking/biking trails nearby
  • Parasailing nearby
  • Ecotours nearby

Key West Sailing Adventures Policies & Fees


Check-in time ends at 5 PM

Check-in time starts at 3 PM

Special check-in instructions:

Special Instructions: Please contact the property at least 24 hours before arrival to make arrangements for check-in.


Check-out time is 11 AM

Payment types

Accepted at this hotel: MasterCard, Visa


Pets allowed


Extra-person charges may apply and vary depending on hotel policy.

Government-issued photo identification and a credit card or cash deposit are required at check-in for incidental charges.

Special requests are subject to availability upon check-in and may incur additional charges. Special requests cannot be guaranteed.

  • Minimum Spring Break check-in age is 21 years old.

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Unless otherwise indicated, the charges below are not included in the overall room price. If not included in the overall room price, they will be charged by the property at check-in or check-out. Charges can vary, for example, based on length of stay or the room you book. This property told us they will charge you for the following:
  • Cleaning fees vary based on length of stay
We have included all charges provided to us by the property. However, charges can vary, for example, based on length of stay or the room you book.
Additional Details

A resort fee is included in the total price displayed. Children 12 years old and younger stay free when occupying the parent or guardian's room, using existing bedding. Some facilities may have restricted access. Guests can contact the property for details using the contact information on the booking confirmation.


Complimentary Half-Day Sail

Book a minimum three-night stay and receive a complimentary half-day sail to the reef off Key West.

Guests must book a minimum three-night stay to qualify. Guests can qualify for this promotion or the sunset sailing promotion, not both during the same visit.

Complimentary Sunset Cruise

Book a minimum two-night stay and receive a complimentary two-hour sunset cruise.

Guests must book a minimum two-night stay to qualify.

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