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

Sat 31 May

Other dates

You can choose the date already on the booking website

Starting at $91.38

Make a reservation

Sat 31 May

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)

asmokymtns

Mar 2025

The crew were so engaging and thoughtful. You can tell they truly love to be on the water! The boat is beautiful, a true gem. We packed some wine and enjoyed a beautiful quiet sail into the sunset!

Archie_W

Mar 2025

This is a low key beautiful way to experience the beauty of the Keys offshore. The staff were so genuine and kind.

JoeLaTravels

Mar 2025

Jonathan and the crew were great! We watched many other “sailboats” motor on by - not sure what their idea was with that. No loud music. BYOB - much more economical and we had one of our own favorite wines.