Key West: Schooner Appledore Day Sail & Open Bar Cruise

Summary

Sailing past key west’s historic seaport with open bar and sea breeze

You’ll sail Key West’s turquoise waters on a classic schooner with a local guide, open bar, and hands-on sailing if you want to join in. Feel sea spray as you pass Mallory Square and historic docks—maybe even take the wheel yourself for a minute or two. It’s relaxed but lively, perfect if you want to see Key West from another angle.

What’s the experience like?

We stepped onto the Schooner Appledore just off the docks near the Key West Historic District, shoes squeaking on the wood. The crew was already joking around—one of them, Mike, handed me a cold ginger ale before we’d even left the harbor. I could smell sunscreen and salt in the air, and somewhere someone was playing Jimmy Buffett from a boat nearby. The sails went up fast, with a few of us helping (I tried, but honestly that rope is heavier than it looks). There’s this moment when you leave the noise of Mallory Square behind and suddenly it’s just wind and water—no cars, just gulls.

Our guide pointed out old buildings along the waterfront as we glided by—the kind of details you’d miss if you weren’t paying attention. He told us about how these schooners used to run sponges and cigars back in the day. I leaned against the rail with a rum punch (yeah, full open bar means they’ll make whatever), watching pelicans dive for fish near the marina. There’s something about seeing Key West from out on the water that makes it feel more real—or maybe just less touristy? Hard to explain.

I took a turn at the wheel for maybe two minutes—felt like forever with everyone watching—and tried not to steer us into Cuba. The sun kept shifting through clouds, so sometimes it was all gold light on the deck and sometimes just this soft blue haze over everything. People laughed a lot; even strangers started talking like old friends after half an hour. Two hours went quick. I still think about that breeze coming off the Gulf, salty and warm, long after we docked again.

Step-by-step itinerary

Day 1 — 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 waterfront
• Pass by Key West Historic Seaport

Top questions

How long is the Schooner Appledore day sail in Key West?

The sailing time is 2 hours total without any stops.

Is there an open bar included on this Key West schooner cruise?

Yes, guests over 21 can enjoy a full open bar during the cruise.

Where does the Schooner Appledore depart from?

The tour departs from docks near Mallory Square in Key West.

Can I help raise the sails or steer during this day sail?

Yes, guests are invited to help raise sails or take a turn at the wheel if they wish.

Are children or infants allowed on board?

Yes, infants are welcome but must sit on an adult's lap during sailing.

Is there a guide on board during this sail?

Yes, an English-speaking guide is present throughout your cruise.

What sights do we see during this Key West schooner cruise?

You’ll pass by Mallory Square and glide along Key West Historic Seaport waterfront.

Are drinks besides alcohol available on board?

Soda and bottled water are included for all guests as well as alcoholic drinks for adults.

What’s included

Your day includes two hours of sailing aboard a classic schooner with an English-speaking guide, unlimited soda and bottled water for everyone plus an open bar for those over 21—all while gliding past Mallory Square and Key West’s historic seaport before returning to shore together at sunset or close to it.