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)

mludolph

May 2022

This is always the highlight of a trip to Key West. I have done this cruise 3 times. Capt Ron and his crew are always fantastic. The sightseeing is amazing and to feel the wind in the sails when you get a turn at the wheel is something you won’t soon forget. The cannon firing at sunset caps an unforgettable trip.

Response from Host

May 2022

Hello Mark - Thanks a lot for taking the time for this review. We really like knowing that our passengers enjoy their experience with us. Also glad to find out that we got to share your birthday with you on this trip :0)

smay7177

May 2022

An amazing vessel, wonderful crew! BYOB sit back and relax and enjoy your evening sunset cruise aboard the Jolly Rover II. I will put this on the top of my to-do list and highly recommend you look them up if you get the Key West.

Response from Host

May 2022

Thanks for choosing to sail with us and for taking the time for this great review and recommendation! Very much appreciated! Glad you like the Rover as much as we do. Look forward to having you all on board with us again. Sincerely, Bill Malone

MMThomas66

May 2022

We really enjoyed the experience of this boat. There was no food offered but experience was excellent. We were allowed to pull the sales up and actually sale to the boat as well which is a lot of fun.

Response from Host

May 2022

Thanks for choosing to sail with us on the Rover and for taking the time to write this review. Very glad to hear that you enjoyed the experience. That is what we strive for! It means a lot to us knowing that you felt your time with us was excellent! Hope to see you onboard with us again. Thanks again. Sincerely, Bill Malone