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Address: 201 William St, Historic Seaport, Dock E 10, E 11 & E 12, Key West, FL 33040-6679
Phone Number:
+1 305-304-4911

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 46 reviews
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The BEST WAY to experience Key West

Nothing wrong with staying at a 5 star resort, with high thread count sheets, and hot tubs, and room service. That is a valid way to vacation. However, the real Key West... read more

Reviewed 11 March 2017

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46 Reviews from our TripAdvisor Community

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Showing 45: English reviews
Level Contributor
58 reviews
24 attraction reviews
common_n_attraction_reviews_1bd8 12 helpful votes
Reviewed 11 March 2017

Nothing wrong with staying at a 5 star resort, with high thread count sheets, and hot tubs, and room service. That is a valid way to vacation. However, the real Key West experience is to score the Key West sailing Experience. Captain Albert and crew have always been fantastic to work with. If you haven't tried "liveaboard" lodging, we urge... More 

Thank tapwaterconchs
Level Contributor
1 review
Reviewed 5 September 2016

It was my first time in Key West and after having myself video'd in front of the Hemingway Estate Ronda, who has been living in Key West with Capt Al knew from my reviews that I was a very adventurous diner and that she needed to cover all of my vacation bases so she planned a nice day out on... More 

Thank Harvey H
Kansas City, Kansas
1 review
Reviewed 13 May 2016 via mobile

Had wonderful time . Spent two nights at dock and one overnight on water . Had wonderful dinner at anchor watching million dollar sunset on water . Thank you Kevin and Jenny !

Thank KP7777777777
Minneapolis, Minnesota
1 review
Reviewed 24 March 2016 via mobile

We are a family of four (kids 8 & 12). We spent two nights on the Wild Thing and went out for an all day sale. If you are a family that enjoys the outdoors I highly recommend this experience. The boat has everything you need for a comfortable stay. Location is fantastic in the heart of Key West. Our... More 

Thank Brickhouse19
Saint Paul, Minnesota
Level Contributor
4 reviews
Reviewed 15 March 2016

My husband had set up the sunset cruise weeks prior to our arrival. We also had an email confirmation. When we arrived at the dock i don't think Captain Al even knew who we were. He was pleasant but asked what we were there for. The day was too windy to go out, which we understood, but he did not... More 

Thank Nancy H
Fairfax, Virginia
Level Contributor
23 reviews
8 attraction reviews
common_n_attraction_reviews_1bd8 4 helpful votes
Reviewed 24 February 2016

One of the best long-weekends yet! We arrived to be met by Capt. Al and a full cooler of drinks on board of the 38’ O’Day – Obsession. The boat was nice and clean and well appointed, very comfortable for two couples. There was always crew around but never obvious to us unless we needed something and they were more... More 

Thank scott s
Level Contributor
11 reviews
common_n_attraction_reviews_1bd8 8 helpful votes
Reviewed 31 December 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
Reviewed 3 March 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
59 reviews
15 attraction reviews
common_n_attraction_reviews_1bd8 24 helpful votes
Reviewed 27 February 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
Reviewed 11 January 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

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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?
  • How should I dress for this tour?