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“An authentic sailing experience!”

Sunset Sail Key West
Book In Advance
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$79.00*
and up
Sunset Sail on Historic Schooner
Certificate of Excellence
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Attraction details
Recommended length of visit: 2-3 hours
Owner description: There's no better way to experience the Florida Keys than right on the water, and there's no better charter to trust with your tour than Sunset Sail Key West. With years of experience and a lifetime of passion, our fleet of locally owned sailboats and personable sailors will show you all the beauty that Key West has to offer. As you join us for a sunset, starlight, or snorkel sail, you'll find that the sparkling waters of the Florida Keys have a way of bringing people together. Our dedicated team is flexible, accommodating, and dedicated to making your sailing experience as smooth and personalized as possible.
Reviewed January 4, 2014

My friends didn't want to go on a big, crowded party cruise. We saw the HIgh Tide and went over to talk to Captain Cassie and first mate Kayla and they were able to take us on a sunset cruise leaving that evening, leaving in just a few hours! They are both very sweet and accommodating. My two friends and I enjoyed the intimacy of a smaller vessel, being closer to the water, and feeling a part of the sailing experience. Very cool and unique experience! Highly recommended!

1  Thank Michelle O
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
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458 - 462 of 494 reviews

Reviewed December 24, 2013

Our sunset sail with Capt. Cassie was, without a doubt, the best part of our vacation. Her boat is beautiful and she is friendly, charming and a perfect hostess. You're allowed to bring your own beverages -- we brought a bottle of wine and Cassie provided glassware and ice. To our surprise, she also brought out a lovely tray of delicious cheese and crackers. We had a blast and will absolutely be back ASAP.

2  Thank dip_out
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed December 16, 2013

We are avid sailors, and had a wonderful sailing with Cassie and her first mate Kayla aboard High Tide! Cassie holds a USCG masters 100ton license and has thousands of sea miles under her belt. She and Kayla are knowledgable, smart, funny, happy, and just great to spend the day with! High Tide is a beautiful sloop and is a proud reflection of all the hard and wonderful work that Cassie and Seth put into her restoration!

2  Thank Nick A
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed December 12, 2013

Our afternoon with Captain Cassie on the High Tide was so fun - a perfect weather sailing day! So nice to have the boat for our family without a large group excursion - highly recommend this private charter.

2  Thank Carol D
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.
Reviewed December 12, 2013

Cassie was referred by our son who is a licensed captain in Key West. We took a mid-day sail with Cassie on a near perfect sailing day. This is a great boat, in excellent condition, and we had a great day. It can handle up to six individuals and is highly preferable to the larger groups one often experiences in Key West...unless you like more strangers and more crowds. Cassie was conscious of where to get the best winds and still be safe. I can't suggest any concerns or changes. Cassie is lovely and a great communicator. We'll sail with Seth and Cassie every time we're in Key West. We recommend this boat and sailing experience undonditionally.

2  Thank Benson1520
This review is the subjective opinion of a TripAdvisor member and not of TripAdvisor LLC.

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