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.

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.

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.  GO TO WEBSITE