Key West Schooner Jolly Rover



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.

One of the most sought after things to do in Key West, these regularly scheduled sunset sails are perfect for adventurous families or couples seeking a romantic interlude at sea.


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.

What’s Included?

  • Romantic Key West Sunset Sails
  • Two Hours Nightly
  • Bring Your Own Food / Beverages
  • Terrific Value

Scan here to download this tour to your mobile.

What You’ll Discover

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!

Departure Time

• Varies seasonally, call for current time

Not ready to book this Boat Trip yet? Browse our full selection of Key West Sunset Cruises and Key West Boat Trips. We’re the Florida Keys travel experts with all the top things to do in Key West.

Know Before You Go


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!

Departure Location

Key West Historic Seaport

View Larger Map

Previous post:

Next post: