Sunset Sail Cruise in Key West

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 onl

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!

From: $0.00

Location: Key West

What's Included

Community Discussion

Q&A

Q: Can kids join on the Sunset Sail Cruise or is it just for adults?

A: Yes! Kids are definitely welcome on the Sunset Sail Cruise. It’s a family-friendly experience, so everyone can enjoy the cannons and the beautiful sunset together. Just keep in mind that there are spaces where younger kids might need to be watched closely, like near the sails or around the cannon area. Overall, it's a fun time for the whole family!

Q: What should I wear for the sunset cruise? Is it casual or more formal?

A: Casual is definitely the way to go! You’ll want to be comfortable since you might be moving around a bit. Light layers are recommended since it can get a bit breezy on the water. Also, don’t forget a hat and sunscreen if you’re prone to sunburn.

Q: What happens if the weather doesn't cooperate?

A: The cruise will only be canceled for severe weather, like thunderstorms or high winds. If it does get canceled, they’ll usually offer a reschedule or a refund, but it's best to check their policy ahead of time. Make sure to monitor the weather the day before your trip!

Discussions

Just booked the Sunset Sail in Key West! Any tips?

Hey everyone! I just booked the Sunset Sail Cruise on the Jolly II Rover for next month and I’m so excited! I've heard it's such a chill experience with no loud music, just the sound of the sails. I love that they even have cannons! Does anyone have any tips for the best time to arrive or what snacks I should bring?

Sunset Sail Cruise was unforgettable!

I just got back from the Sunset Sail in Key West last night and wow, it was amazing! The view was stunning, and being on the Jolly II Rover felt so authentic with the sails up. The crew was super friendly and we even got to shoot the cannon! Highly recommend this for anyone looking to celebrate something special.