Key West Schooner Sail & Full Bar: 2-Hour Tall Ship

★★★★★★★★★★ 4.91 (113 reviews) 96% rated it 5 stars

Free cancellationTravelers' pick

1/5

Duration2h

GroupUp to 49

LanguagesEN

Mobile ticketAccepted

Raise the Sails on a 19th-Century Tall Ship in Key West

You board at the Key West Historic Seaport, help the crew raise the sails on a traditional tall ship, and take a turn steering. The two-hour sail includes a full open bar, water, and guidance from an English-speaking crew member. No stops, no transfers — just the boat, the water, and the thing you came for.

Step-by-step itinerary

Sail and explore Key West waterfront

Board the 2-masted schooner
Help raise the sails
Take a turn at the wheel
Enjoy sailing on the Gulf of Mexico
Pass by Mallory Square
Pass by Key West Historic Seaport

The Experience

There's something about standing on the deck of a real schooner that makes you want to move. Not because you have to, but because the crew is about to hand you a rope and ask you to help hoist the sails. The Appledore is a 2-masted vessel that sails out of Key West's historic seaport, and the whole point of this sail is that you're not just watching — you're part of it. The boat leaves from the waterfront near the old buildings and shops of the seaport, and within minutes you're helping raise canvas the way sailors have done for centuries.

The sail itself runs two hours, no stops, which means you're on the water the whole time. The decks are wide enough to move around, and there's a full open bar for anyone over 21, so you can hold a drink in one hand and take a turn at the wheel in the other. An English-speaking guide walks you through what's happening — why the sails catch the wind the way they do, how to read the water, what the crew is doing and why. It's not a lecture. It's someone who knows the boat talking to people who are curious about it, which is a different thing entirely.

The Appledore is old-school in design but modern in how it's built, so the ride is steady and the railings are solid. Bottled water and soda are included, and the bar is genuinely open — not a token pour but a real one. Infants can come along if they sit on an adult's lap, and the crew says it's suitable for all fitness levels, which means you don't need to be an athlete to do this. You just need to want to be on a boat with your hands on a rope and the Gulf of Mexico in front of you.

What’s included

Your sail includes a full open bar for guests over 21, bottled water, soda, and an English-speaking guide who walks you through the sailing and invites you to help raise the sails and take a turn at the wheel. The two-hour experience departs from the Key West Historic Seaport with no additional stops.

Good to know

Easy physical levelPets welcomeInfants must sit on laps

Operated by Key West Schooners

Is this one for you?Book this if you want to actually do something on the water rather than watch from a seat — the hands-on part is what makes the difference, and the bar means you can relax between turns at the wheel.