- FareHarbor booking partner
- Partnered with Mr Happy Hour Key West
- Locally owned in Key West
A romantic sunset sail with a touch of carribean piracy.
To book, you're calling Josh. He's a Key West local and books it for you at $10 off.
- FareHarbor booking partner
- Partnered with Mr Happy Hour Key West
- Locally owned in Key West
Sail into the sunset aboard the Jolly II Rover, one of the most photographed ships in Key West, with a touch of Caribbean pirate flair. It's BYOB with water included, and there's plenty of comfortable seating on the spacious deck.
What's included
- One of the top Key West sunset sails
- The most photographed ship in Key West
- BYOB with water included
- Spacious deck with plenty of comfortable seating
The locals say“It's the only BYOB sunset sail on the island and it's great!”
What people say
An absolute gem! This is a real, beautiful schooner, not a generic catamaran designed to pack in 50+ people and sell them drinks. There is a pirate aspect - including cannon fire - but it is low-key and not over-the-top cheesy. The owner and staff are great. If you like, they will let you help with the sails and the sailing. Highly recommended!
My husband & I did the sunset sail on Saturday evening. We were looking for a relaxing, beautiful trip, and Jolly Rover II delivered! It was a beautiful sail out to see the sunset, with a knowledgeable and fun crew. From cast off to 'firing' at 'enemy ships' to the singing of a sea shanty as we returned to harbor, it was a fun time. Also had the opportunity to learn a bit about sailing in the process! We were looking to avoid a loud, crowded party boat atmosphere, and Jolly Rover delivered the experience we were looking for. Would do it again & definitely recommend if a fun, peaceful sunset sail is the goal.
Where is this happening?
Why is it cheaper here?
Once the day arrives, an unsold spot is money an operator never gets back — whether it's a seat on the boat, a place on the tour or a ticket to the show. They'd rather fill it at a last-minute price, and we negotiate those spots for you. Same experience — you just booked late.
