Where to Drink: the 8 Best Key West Bar Tours

1.Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt

★★★★★★★★★★4.5 · 549 reviews · 2 hours (approx.) · from $32Our pick

Start at 8:30 p.m. on Greene Street for a two-hour walk through Old Town with guides such as Gene Beach or Sarah. Visit Captain Tony’s Saloon, the haunted Hard Rock Cafe, Porter Mansion, Robert the Doll’s home, and more. Drinks cost extra, but your souvenir T-shirt is included.

“We are on our honeymoon in key west and decided to do this tour. Gene was amazing and kept the whole experience fun and entertaining”

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

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

Follow a local guide through five Key West bars, from Duval Street to the Historic Seaport and back. Your $42.95 ticket includes one beer or mixed drink at each stop, live music, local stories, and a free souvenir t-shirt. Guides such as Sarah, Brian, Laurie, and Garrett keep the night moving.

“It was a great way to see other bars and at the same time get some history and ghost stories. We had fun and would definitely book this again.”

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

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

Cruise Key West’s harbor aboard a six-person tiki boat for about two hours. Bring your own drinks and snacks; the crew supplies ice, cups, water, a blender, music, and life vests. Captains such as Madison, Morgan, Jimmy, and Cristen are known for friendly island stories and sunset views.

“This was a great experience. Capt. Jimmy took us all around the harbor, etc while we drank some ice cold beverages and filled us in on some fun facts while doing so. Weather wasn’t the best (clouds all around) so we didn’t get a picture perfect sunset but we still had a great time! Rain showed up right as we got back to the docks.”

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4.Key West Haunted Pub Crawl Walking Tour

★★★★★★★★★★4.5 · 98 reviews · 2 hours (approx.)

Start at Shots & Giggles at 8 p.m. and walk through Key West with a local guide, stopping at haunted pubs, St. Paul’s Church, La Concha, and Captain Tony’s Saloon. Guides such as Kris, Boots, Greg, Chris, Cheryl, and Maggie have led engaging versions of this English-language tour. Guests must be 21 or older.

“The tour was nice. The host was excellent. The only thing I have to complain about is when I booked the tour it said free T-shirt and the host knew nothing about it so that either needs to be updated when you book it so people don’t think they’re getting a free T-shirt or I need to figure out where I go to get my T-shirt $60 and I was supposed to get a T-shirt for both of us”

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5.Private Sunset Cruise on an Authentic Tiki Bar Boat

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

Cruise Key West’s harbor at sunset aboard a private thatched tiki boat for up to six people. Your USCG-certified captain handles the boat while you bring drinks and snacks. Expect views of Mallory Square, Sunset Pier, Fleming Key, and the Green Flash, plus Bluetooth music and an onboard restroom.

“Captain Morgan was delightful and the cruise was very enjoyable. It was a great experience and I highly recommend it!”

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6.2.5-Hour Duval Street Pub Crawl

★★★★★★★★★★4.6 · 59 reviews · 2h 30m · from $42

Join guides such as Sarah, Brian, Laurie, or Julie for a 150-minute walk along Duval Street. At five bars, choose a domestic beer or mixed drink, hear Key West stories, meet a social group, and take home a souvenir t-shirt.

“Thoroughly enjoyed tour. Our guide Brian was fantastic. Highly recommend tour”

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7.Bone Island Haunted Pub Crawl

★★★★★★★★★★4.3 · 28 reviews · 2 hours · from $32

Join an English-speaking ghost host for a two-hour walk through Old Town Key West, stopping at three haunted pubs. Hear tales of cursed treasure, voodoo, murder, suicide, and strange deaths, with cocktails available to buy. Gene has led especially well-received tours, and every participant receives a souvenir T-shirt.

“A very entertaining and enjoyable night! Our guide Gene was friendly, funny and very knowledgable, lots of interesting stories about Key West - shame no ghosties on the night, but enjoyed his Key Lime pie recommendation the next day 😋”

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8.Haunted Pub Crawl Walking Tour

★★★★★★★★★★4.7 · 8 reviews · 2 hours · from $34

Follow an English-speaking guide, possibly Chris, through haunted Key West after dark. Visit Captain Tony’s Saloon, Wine-O, The Roost, Key West Theater, Artist House, Dean-Lopez Funeral Home, and Old Town Tavern while hearing stories of cursed dolls, restless spirits, and the island’s darker past.

“Chris was an excellent guide. Her connection to the Keys was felt. My husband and had a great time!!”

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