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)

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.

JudgeCEW

Mar 2022

Enjoyed the view of the schooner from the seats aft of the main sail. Crew very friendly and informative. A beautiful and relaxing evening.

Response from Host

Mar 2022

You all were sitting in the King and Queen seats! Great view of the Rover and the activity. Thanks a lot for sailing with us. We really appreciate your choosing the Rover. Was great having you with us. Hope to see you onboard again, Thank again. Bill Malone - Owner of the Rover.

Kristidee50

Mar 2022

This is my second time on the Jolly Rover and both times it was spectacular. The crew is friendly and accommodating. The ship is never overbooked like a “cattle-boat” and you have plenty of room to move around. The captain lets you take a turn at the wheel and photos. It’s definitely something to experience while in the Keys.

Response from Host

May 2022

Glad to read that you had a great time on both sails with us! And that you liked the Rover and our crew! Thank you very much for this review! The Rover is very easy to move around on - and we are fortunate to have a wonderful crew who handles the boat and can still be available to assist our guests. We look forward have you join us again when you return to Key West. Thanks for choosing to sail with us. Sincerely, Bill Malone