Best Key West Bar Crawls — Our Top 13

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Spend about two hours aboard Sebago’s large Key West catamaran, watching Mallory Square, Fort Zachary Taylor, Sunset Key, and the sun slip below the horizon. Your ticket covers champagne, wine, sangria, liquor, premium beer, soft drinks, shrimp, hors d’oeuvres, and live music. Arrive early for a good bow seat and bring a sweater.

“Great cruise and the staff took great care of us. The hors d’oeuvre were delicious and there were a lot of drink options. The live music had everyone singing and dancing all the way up to the time they walked off the boat. The sunset was Amazing!! I highly recommend this sunset cruise!!!”

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2.Key West Afternoon Snorkel Sail with Unlimited Cocktails!

★★★★★★★★★★4.5 · 1,572 reviews · 3 hours (approx.) · from $59

Sail from Key West’s historic seaport aboard the 69-foot catamaran Marquesa to the Florida Reef, about 7.5 miles offshore. The crew supplies gear, instruction, and safety guidance before you snorkel in shallow reef water. Afterward, enjoy an open bar with beer, wine, cocktails, and soft drinks during the ride back.

“The ride to our location was very comfortable, and the crew was courteous, insightful, and genuinely friendly. While I wish we had more time on the water, both the trip there and back were made even more enjoyable thanks to the crew.”

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

★★★★★★★★★★5.0 · 804 reviews · 2 hours (approx.) · from $122Top rated

Spend two hours sailing Key West aboard the America 2.0, a replica of the 1851 Schooner America. Captain Janet, Captain Rae, and other rotating crews handle the sails while you enjoy beer, wine, Champagne, soda, and plated hors d’oeuvres. Expect Fort Zachary, Sunset Pier, Sand Key Lighthouse, and a sunset run from the water.

“First, this tour took off right on time. Check in at least 15 minutes ahead of departure time- we had not checked in and got a call- I thought that was a nice touch. Captain Rae was amazing- she was so personable and explained a lot about sailing to us during the trip. The crew of Chelsie, Brad and Milo did an excellent job of keeping us in drinks and serving several different apps. We had an amazing time on this trip and I would definitely recommend!”

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4.Key West Craft Cocktail Crawl

★★★★★★★★★★5.0 · 543 reviews · 3 hours (approx.) · from $93

Walk through central Key West with a local guide and visit six characterful bars, restaurants, and hotels. You’ll receive five full-size craft cocktails, two food tastings, and stories about the Hemingway Daiquiri, tiki culture, and local life. Guides such as Rose, Danielle, Mike, and Sharon are known for keeping the small group lively and welcoming.

“Cocktails with a Key West history, really interesting locations, so much Key West history. We are repeating it for 2025!”

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5.Original Key West Pub Crawl: The Best Bars with Free T-Shirt

★★★★★★★★★★4.5 · 356 reviews · 2 hours 30 minutes (approx.) · from $42Best value

Join a 2.5-hour evening walk through Key West’s Duval Street and Historic Seaport. A local guide such as Sarah, Brian, or Laurie leads you to five bars, where you receive one beer or mixed drink at each stop. Expect live music, comedy, a possible magic show, local stories, and a free T-shirt. You must be 21 or older.

“The pub crawl was so fun! Sarah was the best guide and made it so memorable. I would highly recommend and would go again tomorrow!!”

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6.Key West Tiki Bar Sunset Cruise (by the seat) BYOB Adventure

★★★★★★★★★★5.0 · 165 reviews · 2 hours (approx.) · from $80

Bring your favorite drinks and snacks for a two-hour sunset ride on a small tiki boat limited to six people. A USCG-certified captain guides you past Key West landmarks, Mallory Square, Sunset Pier, Fleming Key, and the harbor. Ice, cups, water, music, and life vests are provided.

“Madison was such a great guide! She was upbeat and kept the mood light. We were able to visit a few little spots on our way to watch the sunset and she was very knowledgeable and had several fun little facts. We loved that it was only 6 people max. BYOB was also nice in our opinion, because you get to choose something you know you’d want.”

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

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

Join Key West Schooners at 1:30 pm for a two-hour sail aboard the Appledore, a beautiful historic schooner departing from 200 William St. Expect an English-speaking crew, open bar for adults, water, soda, local history, and chances to help raise the sails. The boat returns to the same spot, with no stops along the way.

“Nice walk, but it was just walking. It wasn't in any tourist spot. More crew fine people.Auto-translated”

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8.Tiki Cocktail Class in Key West, Florida

★★★★★★★★★★4.5 · 74 reviews · 2 hours (approx.) · from $80

At Tiki House Key West, you spend about two hours with an instructor such as Brad or Barry, learning Tiki culture, tasting Papa’s Pilar dark rum, and mixing four cocktails. All ingredients and tools are supplied, including a supervised lesson in safely lighting drinks on fire. The class begins and ends at 203 Duval St.

“This was a lot of fun. The bartender/reacher was very knowledgeable and fun. The drinks were great as well. It was interesting earning about the history of the drinks while making them.”

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9.Private Sunset Cruise on an Authentic Tiki Bar Boat

★★★★★★★★★★4.5 · 67 reviews · 2 hours (approx.)

Take a private two-hour sunset cruise around Key West for up to six people aboard a thatched tiki bar boat. Your USCG-certified captain handles the boat while you bring drinks and snacks, use the Bluetooth stereo, and pass Sunset Pier, Mallory Square, Fleming Key, and other harbor landmarks. Captains have included Robert, Morgan, Jimmy, and Tricia.

“Great tour with a great captain. No restroom on sunset cruise, that was a big disappointment but other than that it was great!”

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10.Key West Waterfront Cocktail Walk to Mallory Square’s Sunset Celebration!

★★★★★★★★★★4.0 · 17 reviews · 2 to 3 hours (approx.) · from $139

Walk from the Waterfront Brewery through Key West’s historic seaport, Front Street, Duval Street, and four food-and-drink stops before ending at Mallory Square. A guide such as Bryan shares local stories while you enjoy beer, cocktails, oysters, conch fritters, and a sunset view. Groups are limited to 10.

“Don't miss this tour! Bryan provided an awesome and informative walk as we sampled oysters, conch fritters and delicious libations. Highly recommend!”

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11.Off-Duval Cocktail Crawl

★★★★★★★★★★4.8 · 15 reviews · 3 hours · from $90

Spend three hours with a local English-speaking guide, visiting more than five bars off Duval Street. You will try five alcoholic drinks and two food tastings, from Hemingway Daiquiris to tiki-era creations, while guides such as Shayla and Sharon share Key West stories and practical dining tips.

“We learned some history and fun facts while visiting unique bars just off Duval. It was nice to have drink choices at most of the locations.”

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12.Old Fashioned Cocktail Class at General Horseplay in Key West

★★★★★★★★★★4.5 · 15 reviews · from $81

At General Horseplay in Key West, you’ll spend about two hours with a mixologist such as Tim or Eric, making three Old Fashioned variations while learning how to pour, measure, dash, stir, strain, and garnish. Eat first, then enjoy this adults-only style drinking lesson at 1:00 pm.

“The whole experience was amazing but wouldn't have been do without Tim! He was a wealth of information on everything cocktail!! Just a wonderful overall experience.”

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13.Cocktail Masterclass

★★★★★★★★★★5.0 · 2 reviews · 1h 30m · from $80

At the Key West Cooking School, expert bartenders lead you through five cocktails tied to island history. Taste First Legal Rum and Pilar Dark Rum, make two drinks yourself, sample three more, enjoy small bites, and take home SWAG. The class is at 291 Front Street and includes gratuity.

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