We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.
Improve this listing
Sponsored by:
Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
Sponsored by:
Get directions
Address: 201 William Street, Historic Seaport, Dock E 10, E 11 & E 12, Key West, FL 33040
Phone Number: 305-304-4911
Description: 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.
read more

TripAdvisor Reviewer Highlights

Read all 39 reviews
Visitor rating
  • 29
    Excellent
  • 5
    Very good
  • 0
    Average
  • 1
    Poor
  • 4
    Terrible
BoomBoomCharter Rules !

We went out on a 2 day with one night at sea sailingtrip with Capt. Chris and Nancy. They took great care of my wife and myself and made sure we had a wonderful time. Conditions... read more

5 of 5 starsReviewed November 8, 2011
Veniluno
Add Photo Write a Review

39 Reviews from our TripAdvisor Community

Date | Rating
  • English first
  • Spanish first
  • Any
English first
Daytona Beach, Florida, United States
2 reviews
3 helpful votes 3 helpful votes
2 of 5 stars Reviewed December 9, 2011

We did the Key West Sampler aboard the Obsession and wish we had paid the difference to go on the Wild Thing. This boat has been poorly maintained and there were numerous issues. The first impression was the smell of the boat, it has a very strong odor in the cabin, either from oil in the bilge, mold/mildew, or a... More 

Was this review helpful? Yes 3
puteaux
Senior Contributor
22 reviews 22 reviews
4 attraction reviews
28 helpful votes 28 helpful votes
1 of 5 stars Reviewed November 14, 2011

We spend 2 nights the the 08/29 and the 08/30 on the boat called "the wild thing". The captain charged us 750 USD the 8/26. When we arrived, we found a boat which was quite grimy : smelly, and the dish was not that shiny.. In the middle of the first night, the air condionning fell down and did not... More 

Was this review helpful? Yes 9
Reviewer
4 reviews 4 reviews
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed November 8, 2011

We went out on a 2 day with one night at sea sailingtrip with Capt. Chris and Nancy. They took great care of my wife and myself and made sure we had a wonderful time. Conditions were according to them not so good but having only sailed on the North Sea it was heaven to us. Amazing what meals Nancy... More 

Was this review helpful? Yes 1
Tampa, Florida
1 review
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed July 1, 2011

What can I say about this long weekend adventure? The entire process from booking to experience was flawless!! I called Captain Albert and also spoke with his lovely wife Rhonda about our long weekend. They were friendly and accommodating and no detail was overlooked. They answered last minute questions without delay. The crew members on the boat (Capt. Chris and... More 

Was this review helpful? Yes 3
Portland, Oregon
1 review
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed May 31, 2011

We saw many dolphin. We also saw a pair of pink flamingo in the wild and many turtles. Our Capt. and 1st mate were great hosts. They had many stories to tell of great adventures. One of my main highlights was watching the moon set. This was a once in a lifetime adventure! (or hopefully twice, ....at least, ....we'll see)

Was this review helpful? Yes 3
Coconut Grove, FL
1 review
2 helpful votes 2 helpful votes
4 of 5 stars Reviewed March 21, 2011

Just returned home from 3 nights aboard S/V Obsession. My family (2 adults, 2 boys ages 8 and 3) had a blast! The boat is in fine shape for her age and very comfortable. Our needs are simple and we would recommend this as a fun alternative to a hotel room to all but our most snobby friends. We went... More 

Was this review helpful? Yes 2
Naples, Florida
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed February 22, 2011

we had a two day delightful experience the 38ft obsession, it was roomy and comfortable. if elected to do so the harbor had private and clean showers /bathroom facilities that we used, 300 feet from the sailboat. The cockbit we had breakfast and read the newspaper in the morning before exploring key west on our rental bikes. the two man/woman... More 

Was this review helpful? Yes 1
Denver, Colorado
1 review
12 helpful votes 12 helpful votes
1 of 5 stars Reviewed August 22, 2010

This boat is in need of cleaning, maintenance and smells. As a captain and former live-aboard, I could not recommend this boat to anyone. It smells of septic tank and is full of junk. Half of the interior lighting doesn't work and there are no standard live-aboard amenities. The owner/captain is a nice gent and very knowledgeable of the area... More 

Was this review helpful? Yes 12
Farallon, Panama
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 7, 2010

Whenever I am in Key West I stay on one of thier boats. It is much better than a Hotel and we get to go sailing. The Captain and crew are friendly and fun to be around. I highly reccomend them, not only for a place to stay but for the sailing adventure of your life

Was this review helpful? Yes 1
Orlando, Florida
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed August 6, 2010

Key West is known for being laid back, and what better way to really kick back than by staying on your own sailboat for the weekend? I went down there about 2 years ago with some college friends and we stayed on a beautiful sailboat in the historic marina. Capt. Albert is one of the most interesting people I've met... More 

Was this review helpful? Yes 1

Travelers who viewed Key West Sailing Adventure also viewed

 

Been to Key West Sailing Adventure? Share your experiences!

Write a Review Add Photos & Videos

Owners: What's your side of the story?

Register now for free — and start getting automatic notification of new reviews, responding to traveler feedback, adding new photos to your listing and much more.

Manage your listing

Questions & Answers

Questions? Get answers from Key West Sailing Adventure staff and past visitors.
Posting guidelines
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?