THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Board the Jolly II Rover in Key West’s Historic Seaport for a two-hour tall-ship sunset sail. Help raise the sails, steer, or simply watch the islands and shoreline glow as the crew navigates toward the open Atlantic.
Board the Jolly II Rover in Key West’s Historic Seaport for a two-hour tall-ship sunset sail. Help raise the sails, steer, or simply watch the islands and shoreline glow as the crew navigates toward the open Atlantic.
Book with Schooner Jolly II Rover
Book directly with Schooner Jolly II Rover for the best rates and real-time scheduling.
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Operated by Schooner Jolly II Rover · Key West, Florida
The sun slides toward the horizon and the Jolly II Rover unties from the Historic Seaport, red sails catching the late light as the hull hums through Man O’ War Harbor. Passengers spread across teak decks, some helping haul a line, others leaning on the rail watching the city shrink into a strip of lights. The ocean breathes against the bow; gulls wheel and a playful spray dares you to move closer to the rail.
easy.
2 hours.
Suitable for most fitness levels; requires boarding a small gangway and some standing on deck.
Arrive at least 15 minutes before the scheduled departure at the ticket booth on the dock at Elizabeth and Greene streets to check in and board.
Infants are welcome but must sit on laps; service animals are permitted. There’s limited stroller access and no guaranteed wheelchair ramp—contact operator for accommodations.
The cruise supplies bottled water, cups, and snacks; additional beverages may be available on board—check the operator’s policy for alcohol.
Trips may be canceled for safety in severe weather or insufficient traveler numbers; the operator will offer a full refund if canceled at least 24 hours ahead per policy.
Key West’s seaports grew from 19th-century wrecking and sponge industries; Fort Zachary Taylor marks the island’s Civil War-era military role.
Operate responsibly around fragile nearshore habitats—use reef-safe products and listen to crew guidance about wildlife viewing distances.
Schooner Jolly II Rover operates guided outdoor trips and adventures with an emphasis on safety, stewardship, and memorable experiences.
Book with Schooner Jolly II Rover
Book directly with Schooner Jolly II Rover for the best rates and real-time scheduling.
Reserve Now