We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
27/8/2017 28/8/2017
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}

    Key West Sailing Adventure

    201 William St, E Docks 10, 11 and 12, Key West, FL 33040-6679
    Best prices for your stay
    27/8/2017 28/8/2017
    No availability for your dates from these sites
    Traveller (8)
    Room & Suite (6)
    Pool & Beach (4)
    • Excellent91%
    • Very good3%
    • Average3%
    • Poor0%
    • Terrible3%
    Travellers talk about
    “day sail” (2 reviews)
    Non-Smoking Rooms
    Airport Transportation
    Pets Allowed
    Self-Serve Laundry
    3.0 Star Hotel
    All hotel details
    Offers from Key West Sailing Adventure
    Deals (0)
    27 Aug28 Aug
    1 room, 2 adults, 0 children
        Hyatt Centric Key West Resort and Spa
        2,300 reviews
        #25 of 51 hotels in Key West
        The Southernmost House
        675 reviews
        #7 of 51 hotels in Key West
        Southernmost Beach Resort
        5,726 reviews
        #15 of 51 hotels in Key West
        Orchid Key Inn
        2,150 reviews
        #2 of 51 hotels in Key West
        Write a Review
        Turn Your Opinions into Points!
        Turn your opinions into JPMiles
        Turn your opinions into PAYBACK Points
        *You can enroll in only one programme at a time to earn rewards for reviews.
        JPMiles / Payback Arrow
        JPMiles / Payback Arrow
        Reviews (29)
        Traveller rating
        Traveller type
        Time of year

        1 - 5 of 29 reviews

        Reviewed 25 October 2016

        My wife and I went on a half day sail excursion with Saunders and Erin. It was an enjoyable afternoon. The guys were very knowledgeable about the island and suggested places for us to visit and dine. They were excellent sailors and great hosts! Unfortunately...More

        Thank cmmoore59
        Reviewed 17 May 2016

        Great location, great crew and owners. These boats are right outside Waterfront Brewery in Key West Bight (formerly Waterfront market). Steps from Turtle Kraals, Dantes, Schooner Wharf and about 12 minute walk to Duval via (Sloppy Joes/Captain Tony's)Greene St. we have stayed on Obsession and...More

        Thank tapwaterconchs
        Reviewed 8 March 2016

        These boats are in a great location. We only took the short sailing cruise but we're very impressed with the captaining his knowledge (Ryan). The actual furnishings of the boat were just average. We arrived only to find that we had been moved to a...More

        1  Thank 914ej
        Reviewed 1 November 2015

        I have been to Key West many times and stayed at very fine places.Once I found Key West Sailing Adventure, that's it for me. I stayed on "Obession" for a entire week alone.I didn't feel alone, I felt like part of a family. That was...More

        1  Thank 664dreamer1962
        Reviewed 17 October 2015 via mobile

        Amazing time with Key West Sailing Adventure. Albert and his wife was super helpful when I had to change the date. Bryan is an amazing captain and Jerry is the best 1st mate/chef out there. We will be back and cannot wait. Would highly recommend...More

        Thank phmayer
        Hyatt Centric Key West Resort and Spa
        2,300 reviews
        #25 of 51 hotels in Key West
        The Southernmost House
        675 reviews
        #7 of 51 hotels in Key West
        Southernmost Beach Resort
        5,726 reviews
        #15 of 51 hotels in Key West
        Orchid Key Inn
        2,150 reviews
        #2 of 51 hotels in Key West
        • Top amenities
        • Pool
        • Beachfront
        • Restaurant
        • Bar/Lounge
        • Hotel Amenities
        • Children Activities (Kid / Family Friendly)
        • Airport Transportation
        • Self-Serve Laundry
        • Things to do
        • Pool
        • Restaurant
        • Bar/Lounge
        • Price range
        • US$ 331 - US$ 534 (Based on Average Rates for a Standard Room)
        • Hotel class
        • Room types
        • Kitchenette ,
        • Non-Smoking Rooms
        • Number of rooms
        • 6
        • Reservation Options
        • TripAdvisor is proud to partner with Hotels.com, Hotwire and Cancelon so you can book your Key West Sailing Adventure reservations with confidence. We help millions of travellers each month to find the perfect hotel for both holiday and business trips, always with the best discounts and special offers.
        • Location
        • United States >
        • Florida >
        • Florida Keys >
        • Key West
        Add Photo Photos
        Traveller (8)
        Room & Suite (6)
        Pool & Beach (4)
        Hotel & Grounds (17)
        Business Centre & Event Rooms (1)
        The Southernmost House
        675 reviews
        1.66 km away
        Orchid Key Inn
        2,150 reviews
        1.18 km away
        Southernmost Beach Resort
        5,726 reviews
        1.50 km away
        Hyatt Centric Key West Resort and Spa
        2,300 reviews
        .42 km away
        Nearby Restaurants
        Cuban Coffee Queen
        2,310 reviews
        .07 km away
        Eaton Street Seafood Market
        858 reviews
        .23 km away
        Kermit's Key West Key Lime Shoppe
        2,178 reviews
        .19 km away
        Harpoon Harry's
        943 reviews
        .12 km away
        Nearby Attractions
        ​​​​​​​​​Key West Turtle Museum
        41 reviews
        .11 km away
        Dolphin Watch
        727 reviews
        .04 km away
        Key West Eco Tours
        773 reviews
        .07 km away
        Schooner Spirit of Independence
        379 reviews
        .09 km away
        Ask a question
        Questions & Answers
        11 November 2015|
        Response from TortugaSailing |
        We are located less than 1 mile off Key West at Stock Island Village Marina. There is ample fee parking for guests.
        Room Tips
        "Location, access, and unusual experience are the high points. Be aware it is a little like camping, but well..."
        Read review
        "We chose to stay on the Obsession so we could experience a smaller sailboat before we buy one. The Moondance..."
        Read review
        "The bigger the boat the better."
        Read review
        "A little smaller than a hotel room but a neat adventure!"
        Read review
        Is This Your TripAdvisor Listing?
        Own or manage this property? Claim your listing for free to respond to reviews, update your profile and much more. Claim Your Listing