Best Key West Bar Crawls — Our Top 6

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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