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Address: 201 William Street, Historic Seaport, Dock E 10, E 11 & E 12, Key West, FL 33040
Phone Number: 305-304-4911
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Located In Key West's Historic Seaport for 13 years, choice of two...

Located In Key West's Historic Seaport for 13 years, choice of two sailboats for custom sailing charters or you can choose our stay/sail charter that incorporates the best of both worlds. Stay on the boat and sail to the reef with a Captain and Mate at the time of your choosing. Walking distance to the famous Duval Street. We also offer sailing weddings, at sea adventures, international sailing available. Family friendly, romantic setting for couples, anniversaries, birthdays, and special occasions.

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TripAdvisor Reviewer Highlights

Read all 40 reviews
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  • 30
  • 5
    Very good
  • 0
  • 1
  • 4
Outstanding trip with Brian and Jerry

We would unreservedly recommend these guys for a yacht charter. We booked from the UK with no difficulty at all. Captain Albert is the owner of the business and he is extremely... read more

5 of 5 starsReviewed December 31, 2015

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40 Reviews from our TripAdvisor Community

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Level Contributor
11 reviews
common_n_attraction_reviews_1bd8 8 helpful votes
5 of 5 stars Reviewed December 31, 2015

We would unreservedly recommend these guys for a yacht charter. We booked from the UK with no difficulty at all. Captain Albert is the owner of the business and he is extremely easy to deal with by email and telephone. We chartered a boat with crew for half a day and had a mini adventure from Key West out into... More 

Thank sarah_prz
Romney, West Virginia
1 review
5 of 5 stars Reviewed March 2, 2015

Staying on these yachts is the best way to experience the true heart of Key West which, in my opinion, is the historical and surviving nautical, waterman, sailing, fishing and water adventure that thrives in this Historic Seaport. We stayed on the Obsession, a 37' O Day monohull sloop which is older but is well maintained. This vessel is fully... More 

Thank Dave P
Princeton, New Jersey
Level Contributor
21 reviews
3 attraction reviews
common_n_attraction_reviews_1bd8 18 helpful votes
5 of 5 stars Reviewed February 27, 2015

Presidents Day weekend: Capt Al, Captain Steve & Brenda, What a fantastic time we had here with you. Thank you for your friendship, knowledge, cuisine and making our vacation one to remember. Our kids each got a souvaneir dolphin around the corner, and named them Steve and Brenda. Snorkeling, fishing, sailing, dinner, and drinks with friends. I dont think I... More 

Thank GroheCentral
Atlanta, Georgia
Level Contributor
6 reviews
4 attraction reviews
5 of 5 stars Reviewed January 11, 2015

We took the sunset cruise on the Jolly II Rover (the ship with the red sails) and had a blast. The captain (Bill) and the rest of the crew truly made this an adventure to remember! From firing the "canon" at other ships to their cheerful demeanor, it was obvious that they love what they do and shared their enthusiasm... More 

Thank blarnkaren
Greer, South Carolina
Level Contributor
19 reviews
common_n_attraction_reviews_1bd8 13 helpful votes
4 of 5 stars Reviewed May 4, 2014

Our adventure was ok. We did way more motor sailing than we liked but when we asked the capt that we wanted to sail some he obliged. Water was too rough for snorkeling. Tried but didn't see much of anything. Moondance was comfortable - a bit old. Food plentiful. Albert & Ronda are very nice &easy to deal with.

2 Thank Amy P
Marietta, GA
Level Contributor
111 reviews
18 attraction reviews
common_n_attraction_reviews_1bd8 71 helpful votes
4 of 5 stars Reviewed January 26, 2014

My husband and I and another couple decided we needed a Key West adventure for the holidays. We decided to try staying on a sailboat rather than a hotel to make it a unique experience. The reservation process was nice and easy and Captain Albert was an absolute pleasure to deal with. The four of us stayed on the smallest... More 

1 Thank DebieDC
Concord, New Hampshire
1 review
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed January 15, 2014

Did the Key West sampler on Wild Thing, early December 2013. Boat is somewhat dated but clean and very sound. Albert was great. Skipper Brian and First Mate Paula were first rate. Paula is an excellent cook and a wonderful person. Brian an knowledgable navagator around the "skinny water" to and around Boca Grande Key in the back country. If... More 

1 Thank Joe M
Houston, Texas
2 reviews
common_n_attraction_reviews_1bd8 3 helpful votes
5 of 5 stars Reviewed August 30, 2013

We spent three nights on the Obsession, in the marina, with a four-hour sail out to see dolphins. The crew -- Captain Jeff, Nancy, and Jarrod -- were knowledgeable and friendly. We brought our six-year-old daughter Rocket and Nancy was wonderful with her. Rocket was beaming the entire time. I cannot recommend them enough.

3 Thank TXpoisongirl
2 reviews
5 of 5 stars Reviewed August 11, 2013

A must on everyone's bucket list. Captain Albert and Ronda are the perfect host and hostess. On a spur -of-the moment decision, while staying in Central Florida, we decided to take a drive to Key West. We thought we would add a little adventure to our trip by staying overnight on a sailing yacht rather than a run-of -the-mill hotel... More 

Thank Joseph S
Gainesville, Florida
Level Contributor
5 reviews
4 attraction reviews
common_n_attraction_reviews_1bd8 1 helpful vote
5 of 5 stars Reviewed August 9, 2013

I stayed and sailed with Key West Sailing Adventure the first time in the summer of 2004. I had only recently met my wife and was looking to do something romantic. First impressions you know? The location was conveniently placed walking distance from downtown. We drove from upstate and arrived in the late afternoon. The crew was friendly and helpful;... More 

1 Thank Jeremy L

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Typical questions asked:
  • Will you pick up and drop off at my hotel?
  • I have a family of 7. Can your tour accommodate all of us together?
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