Sunset Sail Key West is more than just a private sailing charter, it is the culmination of decades of experience and a lifetime of passion for sailing, and for …
Reviews
Tripadvisor
4.9/5 · 1,234 reviews
5-star
91%
4-star
5%
3-star
2%
2-star
1%
1-star
1%
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Mar 20, 2025
Our small group of six thoroughly enjoyed our sunset sail aboard the When and If! The boat is a beautiful example of a historic schooner and the captain and crew were great. We had a strong breeze so…Full review by PeterKeyWest
Mar 19, 2025
The crew were very attentive and hospitable. The boat is fantastic! Lots of interesting passengers. Thank you!Full review by U5334VDjoe
Mar 10, 2025
The boat is beautiful and well maintained. The crew efficient and I loved how she sailed under the moderate breeze We sailed out of the channel from the marina and lingered on the water to watch a …Full review by heidigaladriel
Coming down for my wife and I’s 15 year anniversary and am very interested in your sunset cruise. -What time do you guys depart in April? -How far do you venture in the sea? -How long is the duration of the sail? Do you stay out until the sun goes completely down? Thanks in advance, and looking forward to booking with you guys!
A:
I don’t work for them but I highly recommend them, most of their trips are at least two hours long and yes they stay out til the sun goes completely down. Great crew and boat. When you …
I don’t work for them but I highly recommend them, most of their trips are at least two hours long and yes they stay out til the sun goes completely down. Great crew and boat. When you book tell Jeff Misty sent ya.
Sunset sail will only let me book 1 person. We would like a cruise for 4.
A:
If you book through TripAdvisor each private sail for up to six people is shown as (1). It's just so you don't get charged 4 times. You can just book 1 or give us a call to sort it out. …
If you book through TripAdvisor each private sail for up to six people is shown as (1). It's just so you don't get charged 4 times. You can just book 1 or give us a call to sort it out. Thanks for asking!
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