Set sail on the Schooner Jolly II Rover in the Florida Keys and witness a breathtaking sunset over turquoise waters. An unforgettable experience blending ocean serenity with vibrant sky-scapes awaits.
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Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels, no special physical conditioning required
Wildlife
History
The Florida Keys Marine Sanctuary, established in 1990, protects the vibrant coral reefs and diverse marine life that make this area a global diving and snorkeling hotspot.
Conservation
This operation emphasizes eco-friendly sailing practices and supports local conservation efforts to maintain the health of Keys’ ecosystems.
Schooner Jolly II Rover
Set sail on the Schooner Jolly II Rover in the Florida Keys and witness a breathtaking sunset over turquoise waters. An unforgettable experience blending ocean serenity with vibrant sky-scapes awaits.
Schooner Jolly II Rover is a traditional tall ship based in Key West, Florida, offering classic sailing experiences on one of the island’s most recognizable vessels. The Jolly II Rover operates from the Historic Seaport and is known as Key West’s famous “Red Sails in the Sunset” tall ship. As the only squared-rigged, topsail schooner in the Historic Seaport, the vessel delivers a visually striking and authentic sailing atmosphere that is frequently photographed by visitors.
Trips on the Jolly II Rover focus on sailing rather than live music, providing ample space for guests to move around, mingle, and take in open-water views. Activities during sails include helping to raise the sails, steering the ship, and participating in playful cannon demonstrations. Guests can choose to be active crew participants or simply relax and enjoy the sunset.
The signature Sunset Sail Cruise highlights Key West’s renowned evening light and waterfront scenery, combining traditional sailing techniques with theatrical touches. The ship emphasizes a social, laid-back experience suitable for couples, families, and visiting travelers who seek an iconic maritime outing. Photography opportunities are abundant thanks to the vessel’s distinctive red sails and classic rigging.
By operating regularly from Key West’s seaport and maintaining a focus on authentic sailing activities, Schooner Jolly II Rover offers a memorable way to experience the island’s maritime heritage and sunset vistas.
Vessel Type
Squared‑rigged Topsail Schooner
Unique tall ship in the seaport
Location
Key West, Florida
Operates from the Historic Seaport
Signature Sail
Sunset Sail Cruise
Famous “Red Sails in the Sunset”
Guest Experience
Hands‑on Sailing
Help raise sails and steer the ship
Secure seats for an unforgettable Key West sunset aboard the iconic red-sailed topsail schooner.
Arrive early for the best views
Getting to the dock at least 30 minutes before departure ensures a good spot and a relaxed boarding process.
Bring your camera
Capture the stunning sunset and wildlife; a waterproof case is recommended for your gear.
Dress in layers
Evening breezes can be cool, so bring a light jacket or sweater.
Wear sunscreen during the day
If you arrive early or stay after the sail, protect yourself from sun exposure.
Camera or smartphone
Capture the stunning views and wildlife during the sail.
Light jacket or sweater
Evening air can be cool, so bring layers to stay comfortable.
Binoculars
Optional but useful for wildlife viewing.
Sunscreen and sunglasses
Protect your skin and eyes during the daytime before the sail.