Key West Sunset Sail Aboard Schooner Appledore

Hoist the sails yourself and steer a tall ship into the sunset

Sail Key West aboard the Appledore, a 2-masted schooner that carries just 36 passengers, where you help raise the sails and take a turn at the wheel while the sun sets over the Gulf. Premium wine, beer, champagne and appetizers are included; the voyage lasts 2 hours and passes the Historic Seaport, Mallory Square's Sunset Celebration, the Navy Mole and Fort Zachary Taylor. Infants sit on an adult's lap; service animals are welcome.

Step-by-step itinerary

Sunset sailing and sightseeing in Key West

• Board the 2-masted schooner
• Help raise the sails
• Take a turn at the wheel
• Sail past Key West Historic Seaport
• View Mallory Square’s Sunset Celebration
• Pass Navy Mole and Fort Zachary Taylor
• Enjoy drinks from the full cocktail bar
• Watch the sunset over the Gulf of Mexico

The Experience

You arrive at Key West's Historic Seaport and board the Appledore, a wooden schooner built in the tradition of 19th-century tall ships but fitted with modern passenger amenities. The deck is spacious—the boat holds only 36 people—so there's room to move, to find a spot at the rail, to stand near the helm. As the crew prepares to sail, you're invited to help raise the sails, an age-old task that turns a sunset into something you do rather than watch. The exhilaration of feeling canvas catch the wind and the boat respond is the moment most people remember.

Once under way, you take a turn at the wheel if you want it, steering the schooner as she passes the Historic Seaport's charming waterfront buildings, then Mallory Square where the Sunset Celebration unfolds on the dock—street performers, live music, vendors—all visible from the water. The route carries you past the Navy Mole, where the big ships dock, and the Civil War-era Fort Zachary Taylor. The painted sky deepens as you sail, and a bartender moves through the deck with premium wine, boutique beer, champagne and cocktails for guests over 21, plus soft drinks for everyone else. Chef's hors d'oeuvres and cocktail shrimp come around as well. The whole sail is 2 hours, no stops, just the boat, the crew, the water and the light.

What’s included

• Premium wine, boutique beer, champagne and full cocktail bar.
• chef's hors d'oeuvres and cocktail shrimp.
• participation in raising the sails and a turn at the wheel.
• 2-hour sunset sail aboard a wooden schooner that has circumnavigated the globe.

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 actively help raise the sails and steer the boat yourself—not just watch from a seat.

Traveler reviews

4.97★★★★★★★★★★

364 verified traveler reviews

5 ★355

4 ★8

3 ★1

2 ★0

1 ★0

Read all the reviews ›

Top questions

Can I actually help raise the sails on the Appledore, or is that just something the crew does?

You're invited to participate in raising the sails—it's part of the experience. The crew will show you how, and you'll feel the boat respond as the canvas fills. It's not required, but most passengers take a turn.

What is Mallory Square's Sunset Celebration that we sail past?

Mallory Square is a waterfront gathering spot in Key West where locals and visitors assemble each evening to watch the sunset. Street performers, live musicians and food vendors set up there, creating a lively scene you'll see from the water as the Appledore sails by.

How many people sail on the Appledore at once?

The schooner carries a maximum of 36 passengers, which keeps the deck from feeling crowded and lets everyone have room to move and find a good vantage point for the sunset.

Is the 2-hour sail the total time, or does that not include boarding and getting back to the dock?

The 2 hours is the total sailing time on the water. There are no stops during the voyage—you sail continuously past the Historic Seaport, Mallory Square, the Navy Mole and Fort Zachary Taylor, then return to the dock.

What drinks and food are included in the ticket price?

Premium beer, boutique wine, champagne and a full cocktail bar are included for guests 21 and older; soft drinks are available for everyone. Chef's hors d'oeuvres and cocktail shrimp are also included.

Can I bring my service animal aboard the Appledore?

Yes, service animals are allowed on the schooner. Infants must sit on an adult's lap during the sail.