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“Experience the heart of Key West!” 5 of 5 stars
Review of Key West Sailing Adventure

Key West Sailing Adventure
201 William Street, Historic Seaport, Dock E 10, E 11 & E 12, Key West, FL 33040
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Owner description: 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.
Romney, West Virginia
1 review
“Experience the heart of Key West!”
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 functional and ready to sail. In fact I was very impressed with how well she did sail. Our crew was Capt. Joe and Mate Jordan who were great folks, very knowledgable and accommodating to our every request. My wife and I have sailed and boated the US East coast and Caribbean and vacationed around water for 25 years and this experience was one of the best. The dock is a 5-10 minute walk to most of the best restaurants, bars and main attractions yet very peaceful at night.

Visited February 2015
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39 reviews from our community

Visitor rating
Date | Rating
  • English first
  • Spanish first
  • Any
English first
Princeton, New Jersey
Senior Contributor
21 reviews 21 reviews
3 attraction reviews
Reviews in 10 cities Reviews in 10 cities
17 helpful votes 17 helpful votes
“A trip well worth repeating”
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 can do Key West any other way again.

Fresh catch at Dante's. Dinner at Smokin Tuna, Key Lime Pie, s'mores on "hobo island". We've enjoyed at all more than words can say.

Thank you all so much,
The Grohes

Visited February 2015
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Atlanta, Georgia
Senior Reviewer
6 reviews 6 reviews
4 attraction reviews
Reviews in 3 cities Reviews in 3 cities
“Don't miss this!”
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 with their passengers.

The best way to view a magnificent Key West sunset!!

Visited January 2015
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Greer, South Carolina
19 reviews 19 reviews
Reviews in 14 cities Reviews in 14 cities
13 helpful votes 13 helpful votes
“Good overall”
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.

Visited April 2014
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This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Marietta, GA
Top Contributor
92 reviews 92 reviews
18 attraction reviews
Reviews in 33 cities Reviews in 33 cities
55 helpful votes 55 helpful votes
“Great experience but make sure you know what to expect!”
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 of their three sailboats, Obsession. it is docked at a lovely marina; very centrally located, so much so that once we parked the car we didn't move it again till it was time to leave (thankfully it was raining a little bit on our last morning which made it much easier to head home). We were easy walking distance to all of the tourist areas and great restaurants and shops.

My husband and I camp regularly so the less than plush Obsession was not a problem for us, we are used to cramped quarters and interesting toilets.....for those not aware of sailboat living the lack of amenities could be a real problem.

When we boarded the Obsession we were greeted by Paola, a lovely lady from Spain who familiarized us with some of the basics of boat living. I do wish that she would have told us about the pull out bed in the main cabin.....Our friends stayed in the main cabin and we were in the smaller one. Had I spent more time in the main cabin I would have figured it out as the bed is similar to the one in our travel trailer. Unfortunately, I didn't spend much time in the cabin so our friends were not comfortable in the tiny berth in the bow of the boat (triangular shaped, really room for one ish). They described sleeping on the couch that was not pulled out as sleeping in a horizontal phone booth.....I happen to notice the pull out part of the bed till we were LEAVING!!!! ARGH!!!!

Johnny and I were quite comfortable in the cabin at the stern. It was small and had its own bathroom. Marine toilets are not much fun and we only used them in the middle of the night when walking to the bath house and getting on and off the boat were a bit hazardous (we felt safe there just getting on and off the boat alone was a little scary sometimes due to the tides).

The Obsession could really use some work. There were exposed trim pieces in our cabin with nails sticking out of them, the cushions were flat, WAY too many pillows in the main cabin (took up SO much space). During the prep for our sailing adventure the drink holder was broken off and the nails were sticking out of that for the rest of our stay.....I think a little work would make the boat a whole lot more comfortable.

Our two sails were a contrast in adventures....the first one with Captain Brian and Paola was somewhat of a disappointment; it was quite short and mostly we sailed with the motor running (sailing?) and we felt like Brian was phoning it in....The second sail was on the largest of their fleet, The Wild Thing. It was a sunset sail and the weather was perfect. The sailboat was very nice; much, MUCH nicer than the Obsession (yep, Captain Brian, in boats bigger is better) and didn't have the condition problems that the smaller vessel has. This sail was much better than the first and we actually sailed part of it....as soon as the sunset was done we were outta there and back to the dock....it was still a great part of the trip.

There are no showers on the Obsession so we had to shower and use the toilets (most of the time) at a bath house a short walk away. Due to our camping experience that was fine with us but might not be for those who did not expect that. It would have been great to know ahead of time. It was interesting to be docked next to the mega yachts all over the place....beautiful but we sure felt the difference when hanging out and walking to and from showers and toilets rather than basking in the glow of pure luxury (which has I price....I know, I know, LOL).

I would definitely do this again some day but on the larger sailboat....Great fun, great friends, great food, a great adventure; just make sure you know ahead of time what to expect!

Visited December 2013
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