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Key West Sailing Adventure

201 William St E Docks 10, 11 and 12, Key West, FL 33040-6679
Traveller (20)
Room & Suite (6)
Pool & Beach (4)
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Check Out— / — / —
Guests1 room, 2 adults, 0 children
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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
69Restaurantswithin 0.5 km
59Attractionswithin 0.5 km
4Room tips


Traveller rating
  • 33
  • 1
  • 1
  • 1
  • 1
Time of year
Traveller type
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  • 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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Response from AWTropea45, Owner at Key West Sailing Adventure
Responded 1 week ago
Hi April! Thanks for those kind words about Obsession and your stay and sail charter with us. We do hope that you will plan that return trip! We will let Ben and Vinny know that you mentioned how you appreciated them on your sailing trip. Thanks again please call on us anytime. Ronda with Albert
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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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Response from AWTropea45, Owner at Key West Sailing Adventure
Responded 1 week ago
Hi from Key West! We so appreciate the wonderful comments and we remember you! Saunders is still in the area and Brian came back to do other things and we see these guys around town. We still have Wild Thing and recently added new boat St. Vitus Dance - a famous sailboat from the Miami Vice Series and hope you will come back - we have had some recent reports that sound like your adventure. Even baby dolphins being shown how to swim under the sailboat by their mammas - yes we still take excursions at sea! Come back soon! Saving a spot for you ! Captain Albert with Ronda
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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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Response from AWTropea45, Owner at Key West Sailing Adventure
Responded 1 week ago
Hi Karen! We have recently acquired a new sailboat, St. Vitus Dance from the Miami Vice series! We would love to invite you to plan another vacation with us. We have been having wonderful excursions at sea, day sailing has been great all spring time. Weather here is just perfect these days. thanks again, Captain Albert with Ronda
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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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Response from AWTropea45, Owner at Key West Sailing Adventure
Responded 1 week ago
Hi Dennis! We still have Wild Thing and invite you to come back soon! We have been getting rave reviews this year too on wonderful experience at sunset as well as at sea overnight excursions. Jeff has moved out of state and Victor has been around doing other fun things; we have a new crew that is wonderful. We just bought the famous St. Vitus Dance from the series Miami Vice and people are really talking this boat up! Lots of fun, still waiting for you. thanks for your kind words, Capt. Albert
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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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Response from AWTropea45, Owner at Key West Sailing Adventure
Responded 1 week ago
Hi Pixie Darling, We are glad you have some fun on Moon Dance...she has been retired and replaced by St. Vitus Dance, a newer 42 ft. Endeavor that we recently got for trips like you took on Moon Dance! This is a famous boat that was the one that was used on Miami Vice the series! It's laid out with the center cockpit and has wonderful nice features! It's about ten years newer than Moon Dance and is a great upgrade getting rave reviews in the few short months we have had her. Thank you so much for this glowing review and it is true life on a sailboat has many advantages for adventurers and great to have fun chartering. Keep us in mind for another "Dance" it just happens we guess that we like dancing. We have been trying to get this new boat for 4 years and think you would like it even more! thanks again, Capt. Albert and Ronda
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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
Do you offer parking? Or is there parking facilities and what is the cost?
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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Key West Sailing Adventure B&B