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All 309 Key West Attractions »

Key West Sailing Adventure

201 William Street, Historic Seaport, Dock E 11 & E 12, Key West, FL 33040
305-295-2631
Ranked #83 of 173 tours in Key West
4.5 of 5 stars 32 Reviews
Type: Tours
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...... more » 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. « less
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32 reviews from our community

Visitor rating
    24
    3
    0
    1
    4
Date Rating
Shepherdstown
2 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed May 12, 2012

I decided to treat myself to a private charter sailing adventure for my birthday, and had the extremely good fortune to connect with Captain Dennis Krinitt of Breezin Charters and his Crew Member April, docked in front of Turtle Krawls and the Schooner Wharf area. First and foremost, I felt safe the entire time under their care, no worries there... More

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Minneapolis, Minnesota
Reviewer
4 reviews 4 reviews
2 helpful votes 2 helpful votes
5 of 5 stars Reviewed April 24, 2012

As an inland sailboat racer, this was fantastic. A two masted racing schooner that speeds past motorized boats using nothing but the wind More

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Walworth
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed April 22, 2012

My husband and I have gone on the sunset sail twice now with Micheal and his crew on the Adirondack111.It's a great Key West experience,we highly recommend it.Big fun,the crew and captain are awesome!You can watch the sunset as you drink wine or sodas,eat shrimp cocktails and cheese and crackers.The ship is beautiful and they really do hoist the sails! More

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tampa, fl
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed April 13, 2012

Sailing in Florida is always an awesome experience and I highly recommend it to anyone! These guys really had their stuff together and made our trip very enjoyable. The boat was comfortable and staying out overnight was the best part! More

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Tulsa
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed March 29, 2012

My wife and I and another couple made two sailings on the Americas 2 in February, a 2 hour day sail and the longer sunset cruise. Captain Ron and his crew were a delight as he offered technical info on the newly constructed replica of the historic schooner, background on the Keys and the historic significance of the straits and... More

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1 review
1 helpful vote 1 helpful vote
1 of 5 stars Reviewed March 10, 2012

I stayed on the SV Obsession with my husband for our honeymoon. We arrived and found the boat to be very unclean with bugs in the drawers and smelling really bad. It appears they were having trouble with their septic tank. We went for a sail the next day and the crew was lovely and the sights of key west... More

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Davie, Florida
1 review
3 helpful votes 3 helpful votes
5 of 5 stars Reviewed January 3, 2012
3
people found this review helpful

Thank you for helping us customize our five day stay with Key West Sailing Adventure! You were right; converting one night for an overnight was really a fun choice! Being at anchor along with the extra sunset, and a half day gave us a lot more to our "adventure" and we came back to Michigan with wonderful memories! More

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Orlando, Florida, United States
2 reviews
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed December 24, 2011
1
person found this review helpful

We went on the America 2.0 in KeyWest last night for sunset sail for 2hrs and it was a wonderful experience. Though it is pricey, $75 per person, it was peaceful due to less people than many of the other boats out there making it nice for our honeymoon sunset adventure together with my husband. The staff was very accommodating... More

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Tampa, Florida
1 review
1 helpful vote 1 helpful vote
5 of 5 stars Reviewed December 24, 2011
1
person found this review helpful

The America 2.0 is such a bad azz schooner fastest on the East Coast when they raise the final sail it is such a feeling of power you feel as if you own the sea!! the sunset cruise out of Key West was perfect. The crew was great even let me steer the ship for a few minutes. Also the... More

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Amsterdam, The Netherlands
Senior Reviewer
6 reviews 6 reviews
Reviews in 2 cities Reviews in 2 cities
20 helpful votes 20 helpful votes
5 of 5 stars Reviewed December 14, 2011
1
person found this review helpful

this was the highlight of our florida trip, amazing. Weather was perfect, staff were delightful and Key west is just the place to be when the sunsets. I hope to upload some photos soon though i will be sad to look through them, this was an amazing place and trip. thanks guys More

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