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

New York City Tours

Unique Activities (21) Transfers & Transportation (103) Tours, Sightseeing & Cruises (113) Entry Tickets (47) Sporting Events (1) Good for Small Groups (6) Seasonal & Holiday Tours (41) Walking Tours (697) Outdoor Activities (20) Limitied Availability Tours (6) LGBT Friendly Tours (4) Family-friendly Activities (7) Solo Travelers' Tours (147) Food & Drinks (27) Travelers recommend (73) Good for Groups (8) Top Activities (18) Guided Audio Tours (3) Art, Culture & History (135) Attractions to explore (38)

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)

Kathyjb1011

May 2022

Excellent Sunset Cruise. Friendly Staff and Knowledgeable Captain! Sail Housting was Amazing! FUN TIME!

Response from Host

May 2022

Hi Kathy - Thanks for taking the time for this review - very much appreciated! BTW - it was your sail hoisting that was amazing to all of us onboard! You certainly put a lot of effort into it! You hoisted the sail that went up the highest of all six of them! Thank you very much for choosing to sail with us! We look forward to seeing you all again. Sincerely, Bill Malone Proud owner of the Schooner Jolly II Rover

ninagO8433IE

May 2022

Unexpectedly surprised by this wonderful Sunset Sail Cruise on the Jolly Rover II. The crew was fantastic. From the moment we received our tickets to the moment we disembarked. Thank you to Elijah, our captain, the beautiful, strong crew members, and the owner, Bill Malone. It was such a memorable experience, breathtaking and fun! John and Nina

Response from Host

May 2022

Hello! Thank you very much for this review! Comments like yours are what makes what we do so much of a pleasure! And so meaningful! Our aim is to provide an interactive experience that allows us to share what we enjoy with our guests. Traditional sailing with a crew that appreciates the experience as much as you do. Oh yeah - and the cannon fire too! Sincerely - Bill Malone - proud owner of the Tall Ship Schooner Jolly II Rover.

darrylb564

Apr 2022

The sunset cruise was extraordinary, and was probably the highlight of our 3 days in Key West. Anyone looking for a quiet cruise viewing the sunset, talking with the crew (and owner Bill Malone if he's aboard!), as opposed to loud party and music cruises, should definitely go with this one. A British guest on the cruise called it a "civilized" cruise, and my wife and I agree! Anyone interested was allowed to "take the helm" and steer for a few minutes. There was a minor glitch with our booking (beyond anyone's control), and let's just say the staff and owner were extremely generous to us in the way they resolved it, far beyond what was necessary. This was excellent all around.

Response from Host

May 2022

Hello Darryl, Thank you very much for choosing to sail with us. And thanks for this great review! We really appreciated your being able to handle our booking snafu! It was a pleasure having the opportunity to meet you both and to be able to talk for a while as well. Im thinking now that maybe we can say that we offer a traditional sailing experience with a hint of "civilized" piracy! Thanks again. We hope to see you when you return to Key West. Sincerely, Bill Malone