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

Thu 26 Feb

Other dates

You can choose the date already on the booking website

Starting at $91.38

Make a reservation

Thu 26 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.

Cancellation Policy

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

Traveler Photos

Reviews (210)

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

25Greg1956

Mar 2022

Such a beautiful and peaceful sail. This is not a booze cruise. It’s a quiet relationship with the wind and the sea and the sunset. Well worth it. Authentic sailing. Super friendly crew. Can’t wait to do it again.

Response from Host

Mar 2022

Thanks a lot for choosing to sail with us and thanks for taking the time for this review. Very well stated. Much appreciated. It was a wonderful sail - wind was just right - air was crisp and we all got a chance to feel what traditional sailing is like. Very glad you were onboard to share the experience with us. Hope to see you onboard again. Sincerely, Bill Malone - Proud owner of the Tall Ship Schooner Jolly II Rover.