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.
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.
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!
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.
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.
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.