Key West: Sunset Sail Cruise on Schooner Jolly II Rover

Summary

Key West tall ship sunset cruise with red sails, cannons, and harbor views

You’ll join a small group aboard Key West’s famous schooner for a true sunset sail cruise—helping raise sails, steering if you want, firing real cannons (seriously!), and gliding past mansions and historic forts with snacks and water included. The sea breeze and those changing colors will probably stay with you longer than you expect.

What’s the experience like?

Ever wondered what it feels like to drift past Mallory Square as the sun drops behind those wild red sails? I hadn’t either—until we stepped onto the Schooner Jolly II Rover in Key West’s Historic Seaport. The deck smelled like salt and old rope, and our captain—barefoot, grinning—welcomed everyone with that easy Conch Republic warmth. There’s no blaring music here, just the sound of gulls and people laughing as they tried to help hoist the heavy canvas up. I got roped into steering for a minute (don’t ask how that went), but honestly, I didn’t want to let go of the wheel.

We cruised out through Man O War Harbor and past Christmas Tree Island. The water was this weird green-blue I still can’t describe. Our guide pointed out Sunset Key’s mansions—tiny figures waving from balconies—and told us stories about pirates firing cannons at passing ships. Speaking of which: yes, they really do fire the cannons. It’s loud enough to make you jump if you’re not ready (I definitely wasn’t). Kids squealed; even some adults did too. There were snacks and bottled water in coolers, but mostly I just wanted to stand at the rail, feeling the wind pick up as we sailed out toward the open Atlantic.

I didn’t expect how quiet it would get when we passed Fort Zachary Taylor—the only sounds were waves slapping wood and someone nearby whispering about how different Key West looks from the water. The light changed so fast; one minute everything was gold, then suddenly it was all pink and purple shadows over Mallory Square. No band playing or anything—just people sharing snacks or talking quietly while waiting for that last bit of sun to drop away behind Sunset Key. I think that’s what stuck with me most: nobody rushing, just this slow hush settling over everyone as we watched it together.

Step-by-step itinerary

Day 1 — Sunset sail around Key West sights

• Board the Schooner Jolly II Rover
• Sail past Historic Seaport of Key West
• Cruise into Man O War Harbor
• Sail by Christmas Tree Island
• View mansions on Sunset Key
• See Mallory Square from water
• Pass Navy Mole and Fort Zachary Taylor
• Cruise by State Park
• Sail into open Atlantic Ocean
• Observe unique daily sunset

Top questions

Is food included on the Key West sunset sail cruise?

Snacks and bottled water are included during the cruise.

Can kids join the Schooner Jolly II Rover cruise?

Yes, infants and small children are welcome; they can ride in a pram or stroller or sit on an adult's lap.

Are there restrooms on board?

This information isn’t specified in the tour details provided.

Does the sunset sail include hotel pickup?

No hotel pickup is mentioned; guests meet at the Historic Seaport.

Is this sunset sail accessible for wheelchairs?

There is no wheelchair ramp but staff will do their best to accommodate wheelchair passengers.

How long is the Key West sunset sail cruise?

The exact duration isn’t listed in these details.

Will there be music or entertainment on board?

No live band or loud music; just sailing with fellow guests and crew.

Can guests help sail or steer the ship?

Yes! Guests are invited to help raise sails or even steer under crew supervision.

What’s included

Your evening includes snacks, bottled water with cups from coolers on deck, a full sunset sail aboard Key West’s Jolly II Rover schooner—with opportunities to help raise sails, steer if you’d like, mingle freely with other guests, and even fire real cannons before returning after sunset.