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

Mon 24 Feb

Other dates

You can choose the date already on the booking website

Starting at $91.38

Make a reservation

Mon 24 Feb

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.
Hand sanitiser available to travellers and staff
Regularly sanitised high-traffic areas
COVID-19 vaccination required for guides
Packaged snacks are provided.

Cancellation Policy

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

Traveler Photos

Reviews (45)

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!

KDNC1234

Apr 2022

Beautiful evening sail. Relaxing and enjoyable; perfect way to watch the sunset. Captain and crew were very friendly. My two younger children were able to steer the ship and one assisted in raising sails. We will sail with them again when we return to Key West.

Response from Host

Apr 2022

Thank you very much for choosing to sail with us. It was a pleasure having you and your family on the Rover with us. We like getting the younger ones behind the wheel and helping out. Makes for a more interactive experience for ever one. We look forward to seeing you all again. Thanks for the taking the time for this review - much appreciated.

dawntY5263CD

Apr 2022

Best experience ever on our last night in Key West! Awesome crew, and Bill (the owner of the boat) mingled with every guest and sharing many cool stories! We would highly recommend this excursion! You will not be disappointed!

Response from Host

May 2022

Thank you very much for choosing to sail with us and taking the time to write this review. Very much appreciated. We do have an awesome crew! They give me the opportunity to mingle with our guests - the highlight of my day! We all love what we do on the Rover! Very glad to know that we can provide a wonderful experience for you on your last night in Key West! Thanks for the recommendation and hope to see you all again on the Rover. Sincerely, Bill Malone