Sunset Sail Cruise in Key West

Overview

Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or loud music. We go sailing! Plenty of room to get up and mingle with other guests. Help raise the sails! Steer the ship! Shoot the cannons! Or just sit back and relax!

City: Key West

Tue 03 Mar

Other dates

You can choose the date already on the booking website

Starting at $91.38

Make a reservation

Tue 03 Mar

Starting at $91.38

Make a reservation

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What's Included

Coolers of ice with cups and bottled water

Snacks

Sunset Sail

Additional Info

Infants and small children can ride in a pram or stroller
Service animals allowed
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Suitable for all physical fitness levels
There is no wheelchair ramp but we will do out best to accommodate wheelchair passengers.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Traveler Photos

Reviews (210)

ninagO8433IE

May 2022

Unexpectedly surprised by this wonderful Sunset Sail Cruise on the Jolly Rover II. The crew was fantastic. From the moment we received our tickets to the moment we disembarked. Thank you to Elijah, our captain, the beautiful, strong crew members, and the owner, Bill Malone. It was such a memorable experience, breathtaking and fun! John and Nina

Response from Host

May 2022

Hello! Thank you very much for this review! Comments like yours are what makes what we do so much of a pleasure! And so meaningful! Our aim is to provide an interactive experience that allows us to share what we enjoy with our guests. Traditional sailing with a crew that appreciates the experience as much as you do. Oh yeah - and the cannon fire too! Sincerely - Bill Malone - proud owner of the Tall Ship Schooner Jolly II Rover.

darrylb564

Apr 2022

The sunset cruise was extraordinary, and was probably the highlight of our 3 days in Key West. Anyone looking for a quiet cruise viewing the sunset, talking with the crew (and owner Bill Malone if he's aboard!), as opposed to loud party and music cruises, should definitely go with this one. A British guest on the cruise called it a "civilized" cruise, and my wife and I agree! Anyone interested was allowed to "take the helm" and steer for a few minutes. There was a minor glitch with our booking (beyond anyone's control), and let's just say the staff and owner were extremely generous to us in the way they resolved it, far beyond what was necessary. This was excellent all around.

Response from Host

May 2022

Hello Darryl, Thank you very much for choosing to sail with us. And thanks for this great review! We really appreciated your being able to handle our booking snafu! It was a pleasure having the opportunity to meet you both and to be able to talk for a while as well. Im thinking now that maybe we can say that we offer a traditional sailing experience with a hint of "civilized" piracy! Thanks again. We hope to see you when you return to Key West. Sincerely, Bill Malone

Stephen_F

Apr 2022

We had gone on this sunset sail with the same couple in 2007, loved it then and we were very happy to find the same company on our visit this year -2022! The owner was very friendly and visited with all the passengers. The crew did an excellent job and gave interesting history as we sailed out into the Atlantic Ocean on a beautiful evening! Everyone could sit and/or move around to get the best pictures. One crew member, Elijah, offered to take pictures of customers with the sunset behind them! They offered snacks and ice and water. We passed some sunset cruises that were blasting music and everyone was standing and drinking - a sunset sail should be peaceful and beautiful which this one was! Highly recommend it and would definitely do it again if and when we visit Key West again!

Response from Host

May 2022

Thanks for this review and recommendation! Was very nice getting a chance to chat with you all while we were out sailing. It truly was a wonderful night on the Rover! Sometimes I think of our sunset cruises as "Serenity on the Sea" with an occasional cannon blast! And we are very fortunate to have an exceptional crew who truly love what they do. I hope to see you all when you return next time. Thanks for choosing to sail with us again. Sincerely, Bill Malone - Proud owner of the Rover!