Tours and Tickets

Private Sunset Sail provided by Sunset Sail Key West

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per group (up to 1)
1 adult
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You'll start at
Key West
See Important Information for details
  • Pass by Stock Island Marina Village
You'll end at
Key West
See Important Information for details
Important Information
Departure Point
Key West, Key West, Florida Keys, Florida
Return Details
Returns to original departure point
  • Private cruise
  • Captain and mate
  • Light refreshments
  • Soft drinks
  • Bottled water
  • Gratuities
  • Hotel pickup and drop-off
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Additional Info
  • Confirmation will be received at time of booking
  • Children must be accompanied by an adult
  • Pricing is per boat/charter
  • A maximum of 6 people per booking
  • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund
  • This is a private tour/activity. Only your group will participate
Cancellation Policy
For a full refund, cancel at least 24 hours in advance of the start date of the experience.
Traveller rating
  • 18
  • 1
  • 0
  • 1
  • 1
Traveller type
Time of year
Popular mentions
Tom wrote a review Dec 2019
2 contributions
We had an awesome time with Dan & Remy. We booked this charter for a group of 5 including my parents and everyone thoroughly enjoyed it. Big thanks to both of those guys for an awesome cruise.
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Date of experience: December 2019
Denis D wrote a review Nov 2019
16 contributions3 helpful votes
An excellent sunset cruise. What was supposed to be a small group of people ended with my wife and I having a sunset cruise to ourselves. Because the original ship was still having work done on it and would not be ready for our trip he offered a cruise for just the two of its or
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Date of experience: November 2019
stacysells wrote a review Nov 2019
7 contributions
Always wanted to try a sail boat this was perfect . We went as a family trip with friends ( couples) brought some alcohol and had a great time. Friendly staff and very informative about the island and what’s around it. They took our pictures and the sunset was great to see .
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Date of experience: November 2019
choirmast wrote a review Oct 2019
pa54 contributions12 helpful votes
Four of us on the High Tide. The crew was great and the ride was smooth. Not a lot of wind that day but the views were spectacular. Such a better experience than a booze cruise on a big boat.
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SlaterTrips wrote a review Oct 2019
7 contributions
Captain Dan and Brennan were so friendly and knowledgeable! Couldn’t have imagined a better pair to navigate the boat. The ride was so enjoyable - both smooth, yet exciting. The views were breathtaking! They were very accommodating and helpful with the food and drinks we brought
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About the operator

Don’t take it from us – here’s what people have to say about this operator.

By: Sunset Sail Key West
Happy day
wonderful family and friend experience. Beautiful boat. Crew was very very knowledgeable and friendly
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Sunset on the When and If
There is nothing like sailing on history. The When and If was Patton's boat and he told his wife "When and if I co
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James S
Crew Was AMAZING in their work and INTERACTING with guests .I would suggest this to anyone visting KEY WEST .Jus
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Pam A
Love in the time of Coronavirus
We were fortunate enough to have this lovely sunset sail despite the fact that as we traveled, the entire country w
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Gorgeous Sunset Sail
We had a great time sailing with Sunset Sail Key West. Two couples did the Sunset Sail and it was Gorgeous seeing t
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Beth P
Beautiful. Perfect. Thank you to the crew!
Our mom, Full Moon Lady had her wish full filled and is forever in the ocean. Thank you to the very compassionate c
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Wonderful trip
Took my grandmother for a sunset sail. Beautiful and historical sailboat, crew was amazing and sunset was beautiful
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Beautiful Sailboat
We loved sunset cruise on this beautiful old boat. The crew was fantastic! It’s a BYOB Cruise, so we were able to
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Barbara M
Quality experience
What an interesting ship! We brought our own beverages and chose from a high variety nut, fruit, and cheese tray (w
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A dream
We had a sunset Sail on the when and if schooner. The captain and crew were fabulous, their customer service was ou
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Great exciting sail
The 6 mature adults went for an afternoon sail on a windy day the captain handled the wind effortlessly and we had
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Amazing Incredible Outstanding
This was my first time in a sailboat and it was AMAZING!!! Spent this experience with my husband and kids! Libby
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Wonderful trip on historic schooner
A sunset tour on the “When and If” was on my bucket list. It didn’t disappoint! Water was a bit rough, but the capt
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Sunset in paradise!
Even though it was unusually cold and windy, we really enjoyed our sunset cruise. The ship was beautiful and the cr
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Sunset cruise review
Great trip - Captain and crew gracious, friendly and welcoming. Boat history and operation a plus. Would definitel
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Key Details
  • Duration: 2h
  • Mobile Ticket Accepted
  • Free Cancellation up to 24 hours in advance
  • Instant Confirmation
  • Languages Offered: English, Spanish
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