15 Tall Ship Sailing in Key West to Get on the Water

1.Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122Our pick

Board America 2.0 at Key West Bight Marina for a two-hour sunset sail past Fort Zachary, Sunset Pier, and Sand Key Lighthouse. Captain Janet, Captain Rae, Captain Dan, and their crews have been praised for friendly service, clear sailing explanations, and hands-on moments such as raising the sails. Beer, wine, Champagne, soda, and plated hors d’oeuvres are included.

“This was our first time sailing on a schooner and it was amazing. Our captain Dan and his crew were all so nice and welcoming. We had such a wonderful evening. We will definitely be back aboard the America 2.0 next year.”

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2.Schooner Sunset Sail with Food & Drinks

★★★★★★★★★★4.9 · 318 reviews · 2 hours · from $122

Sail for two hours aboard the America 2.0, a polished wooden schooner with teak decks and 3,600 square feet of canvas. Enjoy drinks and a personal hors d’oeuvres plate while the crew sails past Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Captain Janet is a favorite on many departures.

“Friendly staff, clean boat, and overall great experience. Would recommend to anyone in the Key West area!”

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3.Key West Sunset Sail Aboard Legendary Schooner Appledore

★★★★★★★★★★5.0 · 251 reviews · 2 hours (approx.)

Spend two hours aboard the Appledore, a globe-circling wooden schooner, sailing from Key West’s Historic Seaport toward Mallory Square and Sunset Key. You can help raise the sails, watch the sun fall over the Gulf, and enjoy beer, wine, champagne, cocktails, soda, and hors d’oeuvres. Arrive early for the boarding pass.

“Wonderful crew and hospitality. Appetizers were wonderful surprise and variety of drinks very good. Loved the Maine connection.”

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4.Classic Key West Schooner Sunset Sail with Full Open Bar

★★★★★★★★★★5.0 · 213 reviews · 2 hours (approx.)

Sail from Key West’s Historic Seaport aboard a classic schooner for about two hours, with a maximum of 22 people. Captain Joe, Josh, and crew members such as Christina, Michael, Molly, and Vitali have hosted recent trips. Expect cocktails, wine, beer, champagne, soft drinks, water, hors d’oeuvres, and sunset views, with no shore stops.

“We had a great time on the Schooner Sunset Cruise. The three young gentlemen running the show did a phenomenal job on all fronts. I highly recommend this excursion. We will definitely be making this a tradition! Thank you for the memories!!”

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5.Key West Day Sail on Schooner America 2.0 with 2 Drinks

★★★★★★★★★★5.0 · 198 reviews · 1 hour 30 minutes (approx.) · from $73

Board the detailed America 2.0 replica in Key West for a 90-minute coastal sail past Mallory Square, Fort Zachary Taylor, Sunset Pier, and Sand Key Light Tower. The crew handles the sails while you watch for dolphins, sea turtles, and waterbirds. Two alcoholic drinks, soda, and water are included, with extra drinks available by card.

“It was really fun, relaxing and the crew was the best. My wife is handicapped and they were helpful with questions.”

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6.Key West Historic Schooner When And If Sunset Cruise

★★★★★★★★★★5.0 · 114 reviews · 2 hours (approx.)

Sail Key West aboard the 1932 schooner When and If, built for General Patton. Captain Matt, Captain Zach, and crew members such as Veronica and Jahn have led recent cruises, inviting you to help raise sail and take the wheel. Select beer, wine, soft drinks, and water are included during this two-hour sunset trip.

“Great crew. They made the trip personal and informative! Beautiful boat and amazing sunset! Highly recommend!”

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7.Key West Schooner Backcountry Eco Tour Sail Snorkel and Kayak

★★★★★★★★★★5.0 · 93 reviews · 5 hours (approx.)

Spend about five hours aboard a traditional double-masted schooner with a small group of up to 20 people. Captain Joe, Sandy, Josh, and crew members such as Michael, Vitale, and Cristina may guide the day, with time for kayaking, snorkeling, sailing under canvas, lunch, and drinks in the Key West backcountry.

“Such a great experience! Captain Sandy and first mate Michael were amazing guides, sailors, hosts and cooks. Highly recommend this 5-hour long sailing, kayaking and snorkeling expedition.”

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8.Schooner Appledore Day Sail with Full Bar in Key West

★★★★★★★★★★5.0 · 89 reviews · 2 hours (approx.)

Set sail from Key West’s Historic Seaport aboard the schooner Appledore for a two-hour cruise with an English-speaking crew, open bar for adults 21 and older, soda, and water. You may help raise the sails, hear local history, and enjoy a calm, traditional sailing experience with up to 49 people aboard.

“We cruised on the Appledore in Maine over the summer and had such a nice time that we cruised with them again in Key West. Enjoyable and relaxing afternoon on the water with a friendly crew.”

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9.Key West Wind and Wine Sunset Sail aboard classic Schooner

★★★★★★★★★★5.0 · 16 reviews · 2 hours · from $133

Spend two hours aboard a classic Key West schooner as the crew raises the sails and the sun drops over the water. You get eight wines, five premium beers, charcuterie, fruit, chocolate, soda, and water. Depart from Opal Key Resort and Marina, with an English-speaking guide and nightly sailing times.

“We had a fantastic time! We were running late and they waited for us which we very much appreciated. 10/10”

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10.Schooner Day Sail with Onboard Bar

★★★★★★★★★★4.8 · 13 reviews · 1h 30m · from $73Best value

Spend 90 minutes aboard the 105-foot schooner America 2.0, sailing past Fort Zachary Taylor, Sand Key reef, Mallory Square, and Sunset Pier. You’ll have padded seating, soft drinks, water, and the option of two alcoholic drinks for ages 21 and older. Bring a picnic, watch for dolphins, and check in early behind Schooner Wharf Bar.

“Wonderful young crew super friendly, knowledgeable and truly cared about their guests. Captain Rae had lots of stories to share while sailing the boat.”

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11.Key West Wreckers Race Aboard Schooner America 2.0

★★★★★★★★★★5.0 · 9 reviews · from $111

Join Captain Janet and the crew of Schooner America 2.0 for Key West’s annual Wreckers Race. After a cannon start, you’ll sail nine miles toward Sand Key Lighthouse alongside up to 30 other boats. Enjoy a boxed lunch, two included alcoholic drinks, soda, water, wildlife sightings, and wide views of Key West.

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12.Key West’s Schooner Appledore Star Champagne Sunset Sail

★★★★★★★★★★5.0 · 3 reviews · 2 hours · from $109

Spend two hours aboard the Appledore Star, Key West’s only bugeye schooner, as the crew raises sail and guides you past Mallory Square, Navy Mole, and Fort Zachary Taylor. Sip champagne, wine, sangria, beer, or a top-shelf cocktail while enjoying chef-prepared hors d’oeuvres and a classic Gulf sunset.

“Petit groupe, équipage au top, très belle autre façon de vivre the sunset à KW”

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13.Key West Night Cruise aboard Schooner America 2.0

★★★★★★★★★★5.0 · 3 reviews · 1 hour 45 minutes (approx.) · from $83

Board the classic Schooner America 2.0 at 202 William Street for a 1-hour-45-minute evening sail along Key West’s waterfront. A crew member points out stars and constellations with a laser, while adults 21 and older receive two rounds of beer, wine, or champagne. Bring a light jacket for the cooler water breeze.

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14.Schooner Full Moon Night Sail with Drinks

★★★★★★★★★★5.0 · 2 reviews · 1h 30m · from $83

Spend 90 minutes sailing Key West at night aboard the teak-trimmed Schooner America 2.0. You’ll watch the shoreline lights, stargaze beneath the full moon, and enjoy two alcoholic drinks if you’re 21 or older, plus soda and water.

“Fabulous experience! This was our first time sailing. 100% recommend!!!”

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15.Stock Island Wind & Wine Sunset Sail aboard classic Schooner

★★★★★★★★★★5.0 · 2 reviews · 2 hours · from $133

Meet your captain at Bad Boy Taqueria at the Perry Hotel & Marina, then board a classic schooner at slip J5 for a two-hour sunset sail. The crew hoists the sails while you enjoy eight wines, five beers, charcuterie, sodas, and water. It suits couples, friends, and anyone who wants a polished but relaxed evening on the water.

“Apps were light but good! Wine and drinks were also nice. Gorgeous evening! We really enjoyed it.”

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