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An Authentic Key West Sailing Experience!

Authentic

Key West Sailing Experience

Come sail Key West’s most photographed ship – the Jolly II Rover, a square-rigged topsail schooner! A Key West sailing adventure aboard the Schooner Jolly II Rover takes you back in time on a classic 80’ tall ship to an era of pirates, rum runners and privateers seeking freedom and solitude. Their spirit of independence lives on daily on the Jolly II Rover.

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Roling Thunder Happy Hour from James Papagno on Vimeo.

The crew from Active Perspectives and Bombarda Rum chose the Rover to set the stage for their latest investment video. They were kind enough to create a short director’s cut for us to use. Cheers gents! (see the full video here)

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Sunset Sail

A top Key West attraction is the Jolly II Rovers famous “Red Sails in the Sunset” 2 hour sunset sail! Take in a memorable sail of Key West’s most famous sights while the sun works its magic turning the sky brilliant colors. With our distinctive red sails and being the only square rigged tall ship in Key West, the Jolly II Rover is the focal point as we sail past the Mallory Square Sunset Celebration. Help raise the sails, fire the cannons, and take your turn at the wheel for an authentic tall ship sailing experience.

More InfoBook online now!

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Key West Day Sail

Day Sail

Our daily 2-hour afternoon sailing tour fits perfectly into your Key West sightseeing trip. Enjoy an exciting Key West sailing adventure on the glistening crystal blue waters, with the Rover’s signature red sails flying! Look for the abundant Florida Keys wildlife both in the air and sea. Find your inner pirate and join the crew while you hoist the sails, steer the ship and fire the cannons!

More InfoBook online now!

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Private Charters

Searching for a truly unique Key West sailing experience that is all your own? Charter your own private Key West tall ship sailing adventure. Whether its a few hours to celebrate a special event or an all day adventure, tell us where you want to go and what you want to experience, then climb aboard! For memories of a lifetime, charter a sunset wedding or an overnight excursion. Boca Grand is only 12 miles outside of Key West and is in a world of it’s own. You can even charter the Jolly II Rover for a private party dock side or anchor overnight experience.

More Info

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Based on 121 reviews.
Kimberly Klimek
Kimberly Klimek
2022-02-17
Verified
We had an excellent experience. The owner and all of the crew were awesome! Highly recommend.
Neal
Neal
2022-02-03
Verified
My Wife and I sailed on this ship last night for a sunset cruise. The staff and experience were more then exceptional! Especially the cannon fire, worth every penny for that alone!
Ben Nesler
Ben Nesler
2021-12-23
Verified
So, first of all, amazing time on board the Rover. Relaxed vibe, lots of “participation” in sailing for the passengers, but what REALLY sets this crew apart is their helpfulness. Upon disembarking, I dropped a Birk into the bay. Fortunately, thanks to the JR mate With the dip net, my sandal was saved!! Cheers to the crew and Captain Bill!
jennifer murray
jennifer murray
2021-12-06
Verified
Great ship and wonderful crew. Not a crazy “party” boat ride (BYOB!). What a beautiful trip. Highly recommended!!
Steve Klayman
Steve Klayman
2021-11-09
Verified
The sunset cruise was one of the highlights of our honeymoon. The captain (I'm sorry, I forget your name) was a wonderful tour guide and his crew was very professional. The boat is absolutely beautiful, as is the local scenery. We were on the cruise where they put up their square (I think) sail for the first time since hurricane season started and it was cool to see how excited the captain was to do it. We will definitely cruise with them again.
Pau Martinez-Munevar
Pau Martinez-Munevar
2021-11-06
Verified
This is our second time on this sunset cruise. We absolutely loved it! The boat is beautiful, with a lot of character. We have two boys, 5 and 7 and it was perfect for us. They got to raise the sail, and play captain for a little while. At the end they received a small bag with a little treasure as a keepsake! We were able to bring our own drinks and snacks too which was perfect. The staff was super friendly. We saw some of the other boats extremely crowded, some with loud music. Definitely more of a party vibe. But if you are looking for a more intimate experience on a sailboat, and family-oriented, this one is perfect. Highly recommended and planning to using them in the future.
Jeffrey Bean
Jeffrey Bean
2021-11-05
Verified
Great value and crew were fun
Marsha Frank
Marsha Frank
2021-11-04
Verified
The best sail ever! This is not s booze cruize. This is serious, spiritual, life changing sailing!
Nor'Easter Carpentry
Nor'Easter Carpentry
2021-11-03
Verified
Kay Thacker
Kay Thacker
2021-10-25
Verified
Great time, wonderful time.
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Key West

Experiences

Key West Experiences

Key West Lighted Boat Parade

Join the Crew of the Jolly II Rover and parade through the Historic Seaport of Key West showing off the ships holiday décor! Enjoy a starry night, a festive atmosphere and thousands of twinkling lights on this entertaining evening cruise. Bring your own choice of food and beverages, bottled water snacks of crackers and cheeses included.

Key West Wreckers Race

The “day of wreckoning” reenacts times in Key West history when wreckers raced to a disabled ship, rescued the crew and laid claim to the cargo! Today, there is nothing to rescue except bruised egos from the last race. Join the Schooner Jolly II Rover for a day of rivalry, fun and radio insults on the high seas! Enjoy an exciting sailing adventure among a multitude of sailing vessels all competing for fun!

Key West Civil War Days


Join the crew of the Schooner Jolly II Rover for this very exciting and famous, annual Battle of the Schooners!! Re-enactors in period costume will be onboard as the Schooner Jolly II Rover defends its position in the harbor against opposing forces from both land and sea! This is a very popular and very exciting event. Seating will be limited to 16 passengers and ear protection will be provided to all passengers.

Boy Scouts

Currently operating year round out of the Historic Seaport of Key West, Florida, the Schooner Jolly II Rover is the only square rigged, topsail schooner contracted with the Florida National Boy Scouts of America High Adventure Sea Base Program. The Jolly II Rover provides boy scout troops with week long sailing, snorkeling and fishing adventures in the beautiful waters of the lower Florida Keys through the months of June, July and August.

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Over the years, the Schooner Jolly Rover has been featured in countless magazines, newspapers and blogs for our iconic red sails and legendary sunset cruises. Read them here.

Like us on
Facebook

Join us on Facebook HERE.

Frequent Sailor Discount!

Many locals as well as visitors are repeat sailors. And we love seeing familiar faces, so we offer $15 off your second sail and your third sail is FREE!

*Within 30 days.

Where to
Find Us

Click HERE for the Map

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305-304-2235  BOOK ONLINE