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Key West Sailing Adventure

Traveller (20)
Room & Suite (6)
Pool & Beach (4)


Our three sailboats are located side by side. Perfect for a family vacation, wedding and honeymoon at sea, restate vows at sunset, couples getaway romantic weekend. Plan a corporate retreat, book one or all three. This is more like a boatel with economy to larger vessels in choices. 44 foot Morgan, 42 foot Irwin or 37 foot O'Day to choose from; each have unique personalities.
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Property amenities
Airport Transportation
Children Activities (Kid / Family Friendly)
Non-Smoking Hotel
Pets Allowed ( Dog / Pet Friendly )
Self-Serve Laundry
Room features
Non-Smoking Rooms
Good to know


Full view
97Great for walkers
Grade: 97 out of 100
68Restaurantswithin 0.5 km
60Attractionswithin 0.5 km
4Room tips
Traveller rating
  • 33
  • 1
  • 1
  • 1
  • 1
Time of year
Traveller type
  • Filter
  • English
Popular mentions
My husband, 8yr old daughter, and I had an amazing time staying on the Obsession. The boat was larger than we expected and had everything we needed to feel at home. The location was close to all the fun of Key West and felt miles away too. The best part was sailing out to the
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I would like to start off by saying Albert, the owner of these boats, was so pleasant to work with. He checked in with me the week before our trip because of some weather concerns. He followed up with me the day of arrival, the morning of our overnight venture and the day we
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We had a great mini vacation and enjoyed our stay! Wonderful! Close to restaurants and shopping! Did some sailing, capt and crew were awesome! This was quite a great adventure! Thank you for the hospitality and great memories!
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Excellent experience, Jeff and Victor were awesome crew members and very friendly and accommodating! Sunset was spectacular! Even went for a swim halfway the trip with my sister and my dad. Great memories.
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My two best friends and I stayed on the Moondance, the largest of the 3 boats. (2 bed/2 bath) for 6 days. (3 at the docks, 3 at sea) Albert was great to deal with and was very helpful during the booking process. The kitchen is small and the fridge is an under counter unit.
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All photosTravellerRoom & SuitePool & BeachBusiness Centre & Event Rooms
Living room
Evening sunset
Sunset at Casa Marina
Our view every morning.
Photo provided by managementKey West Sailing Adventure
Enjoy a free two hour sunset sail with a two day stay charter package
We are located less than 1 mile off Key West at Stock Island Village Marina. There is ample fee parking for guests.
0 votes
"Location, access, and unusual experience are the high points. Be aware it is a little like camping, but well worth it!"
"We chose to stay on the Obsession so we could experience a smaller sailboat before we buy one. The Moondance and Wild Thing are nicer sailboats, but the Obsession was very nice."
"The bigger the boat the better."
"A little smaller than a hotel room but a neat adventure!"
United StatesFloridaFlorida KeysKey West
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