Key West’s Most Exciting Daily Sails and Private Charters
Sail back in time aboard the Schooner Jolly II Rover. Rediscover old world sailing on a classic 80’ Caribbean coastal sailing ship -- the same kind used by infamous pirates, rum runners, and those who first sought the freedom and solitude of the Florida Keys hundreds of years ago. Their spirit of independence and adventure lives on daily as we sail Key West and her crystal clear waters with authenticity; Jolly II Rover is the only square rigged, topsail Schooner sailing out of the Historic Seaport of Key West.
- Romantic Key West Sunset Sails
- Two Hours Nightly / Open to the Public
- Bring Your Own Food / Beverages
Key West Sunset Sails – Romantic Sightseeing Adventures
Daily Sunset Sails depart Key West’s Historic Seaport nightly. One of the most sought after things to do in Key West, our regularly scheduled sunset sails are perfect for adventurous families or couples seeking a romantic interlude at sea. And, starting at only $35 per person, Jolly II Rover sunset sails are among the most affordable Key West activities.
Bring your own food and drinks, and let us transport you to a time when sailors were one with the ocean. Join the crew and hoist the sails, or just sit back, relax and take in the experience. Revel in the moment as our magnificent red sails capture the wind and the Rover sails off to a place time forgot.
While we’re sailing, be on the look out for all the amazing Key West attractions and wildlife. See dolphins, turtles, and man o’ war jelly fish as we sail near Fort Zachary Taylor, picturesque Sunset Key, and the world famous Christmas Tree Island from the decks of the pride of Key West sailing ships, then watch, wave and smile as other vessels sail in close to give their passengers a glimpse of our magnificent sailing ship with it’s distinctive red sails and tall square rig.
When we pass by famous Mallory Square under full sail, cameras will flash and throngs of land lovers will cheer. The Jolly II Rover presents a memory of a lifetime from the decks of Key West’s most photographed sailing schooner.
Finally, as you sail into the glorious Key West sunset, scan the horizon for the world renowned Key West Green Flash!
A Pirate’s Life for Me!
The Jolly II Rover crew encourages everyone to find their inner pirate while sailing the emerald waters of Key West. Join the crew and show your muscle hoisting the sails! Grab the wheel and prove your salt steering the ship! Let your intrepid spirit shine and fire the cannons!
Built as a mercenary vessel, the Jolly II Rover sails back in time to capture the bygone days of a highly romanticized, infamous period in Key West sailing history when merchant ships, smugglers, and pirates plied the very waters we sail today.
Experience the excitement and anticipation of a real life sailing adventure as the Rover crew trains the cannons and prepares for a broadside cannon fire exchange with a rival tall ship!
This isn’t your everyday Key West Sail - this is a pure sailing adventure aboard the Jolly II Rover. And starting at only $35 per person, Jolly II Rover sails are among the most affordable Key West activities.
Schooner Jolly II Rover
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