Under sail · TALL SHIP SAILING IN KEY WEST

Top 4 Tall Ship Sailing in Key West

4 sailing trips  ·  seats from $122 each

These are the 4 tall ship sailing in Key West to put on the shortlist, each with its price, its time on the water and what comes with the seat. Start at the top and work down.

Key West Schooner Sunset Sail with Bar & Hors d'oeuvres - What sailing on America 2.0 feels like
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Key West Schooner Sunset Sail with Bar & Hors d’oeuvres

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

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122Top of the fleet

Board the replica 1851 schooner America 2.0 at Key West Bight Marina for a relaxed two-hour sunset sail. Captains such as Janet, Rae, and Dan have guided recent trips, while the crew serves beer, wine, Champagne, soda, and plated hors d’oeuvres. You’ll pass Fort Zachary, Sunset Pier, and Sand Key Lighthouse before returning to the marina.

“Sunset was enchanting and the crew was super accommodating! Captain Dan also added historical tid bits that enhanced the Key west experience. Great trip!”

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Key West: Schooner Sunset Sail with Food & Drinks - The route along Key Wests western shore
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Key West: Schooner Sunset Sail with Food & Drinks

2.Key West: Schooner Sunset Sail with Food & Drinks

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

Sail from Key West aboard the wooden schooner America 2.0 for a two-hour sunset outing. The crew serves alcoholic and non-alcoholic drinks plus a personal hors d'oeuvres plate as you pass Fort Zachary Taylor, Sand Key Reef, Mallory Square, and Sunset Pier. Keep watch for dolphins, turtles, water birds, and the Green Flash.

“Amazing cruise. The crew were fantastic, the cruise very relaxing, and the setting sun beautiful to see. Many thanks, a perfect evening.”

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Key West Sunset Sail Aboard Legendary Schooner Appledore - Key West from the water
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Key West Sunset Sail Aboard Legendary Schooner Appledore

3.Key West Sunset Sail Aboard Legendary Schooner Appledore

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

Set sail from Key West Historic Seaport aboard the classic wooden schooner Appledore for a 2-hour sunset trip. You can help raise the sails, enjoy beer, wine, champagne, cocktails, soda, and hors d'oeuvres, and hear sea stories from crew such as Joe, Josh, Christina, Andy, and Pablo. The boat carries no more than 36 people.

“We had a nice time and the crew did a great job with food and drinks. The sunset was very nice and the ship was beautiful. Not sure it was worth the fee, but a good time.”

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Classic Key West Schooner Sunset Sail with Full Open Bar - Leaving from the Key West Historic Seaport
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Classic Key West Schooner Sunset Sail with Full Open Bar

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

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

Set sail from Key West’s Historic Seaport aboard a schooner limited to 22 passengers. Captain Joe, Captain Josh, Cristina, Michael, Molly, or another crew team may handle the trip. Expect a gentle cruise, cocktails, wine, beer, champagne, snacks, and views of Mallory Square, Sunset Key, Fort Zachary Taylor, and the setting sun.

“Very nice professional staff. Fun ride and really liked that only a limited number of people can be on the boat. Did not feel crowded.”

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Other ways to get on the water

Sunset Sailing CruisesCatamaran Sailing TripsSailing and Snorkeling TripsPrivate Sailing ChartersIsland Hopping Sailing TripsTall Ship and Schooner Sailing
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