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Jolly II Rover
Jolly II Rover Sunset Sail
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!
Matt Lamoureux
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.
Stacey Gonzon
See all reviews >
FEATURED TRIP

A romantic sunset sail with a touch of carribean piracy.

by
Jolly II Rover
Sunset Cruise
The Locals say:
"It's the only BYOB sunset sail on the island and it's great!"
normal Price: $
95
/
Ticket
20
Tickets
left
SAVE $
10
Last-Minute Price:
$
85
/
Ticket
starting at:
$
85
/
Ticket
this event is:
FREE!
this event is:
BY DONATION!
Fri
,
August
22
nd
--
6:30
PM
Sat
,
August
23
rd
--
6:30
PM

+ 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

MORE DETAILS >

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12
HR
12
MINS
12
SECS LEFT TO BOOK
BOOKING IS CLOSED
2025-08-22T18:00:00-04:00
2025-08-23T18:00:00-04:00
This unlocks your $10 discount.
This unlocks your free item.
LAST MINUTE KEY WEST
Call the booking number for
Jolly II Rover
and tell them the code!
Go to the booking site for
Jolly II Rover
and enter the code!
(305) 304-2235
BOOK NOW >
Call the booking number for
Jolly II Rover
and tell them the code!
Go to the booking site for
Jolly II Rover
(305) 304-2235
BOOK NOW >
That's it!
But you only have
(time to book)

‍Why the discount?

We negotiate the best last-minute rates for you and fill empty spots that would have otherwise gone unclaimed. There's no catch!

Curious about the full price?

We don't blame you. Go ahead and check the prices on their official website to verify we're telling the truth.

This unlocks your $10 discount.
This unlocks your free item.
LAST MINUTE KEY WEST
Call the booking number for
Jolly II Rover
and tell them the code!
Go to the booking site for
Jolly II Rover
and enter the code!
(305) 304-2235
BOOK NOW >
Here's all the info you need:
OFFICIAL WEBSITE >DIRECTIONS >
That's all there is to it. Enjoy!

‍Why the discount?

We negotiate the best last-minute rates for you and fill empty spots that would have otherwise gone unclaimed. There's no catch!

Curious about the full price?

We don't blame you. Go ahead and check the prices on their official website to verify we're telling the truth.

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Where is this happening?
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!
Matt Lamoureux
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.
Stacey Gonzon
See all reviews >
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