Boozy Tours in Key West: the 15 Worth Booking

1.Key West Sunset Cruise: Dinner, Live Music & Drinks Included

★★★★★★★★★★4.5 · 1,707 reviews · 2 hours (approx.) · from $92Our pick

Board a 65-foot yacht at Key West’s historic seaport for a two-hour sunset cruise with a crew-served tropical buffet, unlimited well drinks, beer, wine, soft drinks, and live music. You’ll pass Mallory Square and the Florida Keys National Marine Sanctuary before returning to the harbor.

“It was a blast. Great crew, great music, excellent fun vibe....all around great experience and the best lemon drop I've ever had from the young blonde bartender on the upper deck”

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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, then snorkel the Florida Reef with provided gear and crew instruction. Afterward, enjoy unlimited beer, wine, cocktails, and soft drinks on the return sail. Bring a swimsuit, towel, sunscreen, and photo ID.

“crew is great worst part was other passengers standing in walkways. Drinks after snorkeling where good with crew working fast to get them out.”

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3.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Set sail from Greene Street aboard Fury’s 65-foot catamaran for two hours of live cover music, dancing, sunset views, unlimited beer, wine, champagne, margaritas, sodas, and seasonal appetizers. You’ll pass Mallory Square and may see Fort Zachary Taylor before returning in time for dinner.

“Fun and drinks great band. Weather was good got to see the sunset it was a great experience highly recommend”

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

★★★★★★★★★★4.5 · 549 reviews · 2 hours (approx.) · from $32Best value

Walk Old Town Key West from 8:30 to 10:30 p.m. with storytellers such as Gene Beach or Sarah, stopping at haunted bars, a former morgue, Porter Mansion, and Robert the Doll’s home. Drinks cost extra, but your $32.20 ticket includes the guided walk and a souvenir T-shirt.

“Great and informative! Gene Beach (narrator) was fantastic! Worth it and it’s a must when in Key West!”

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5.Key West Craft Cocktail Crawl

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

Follow local guides such as Rose, Danielle, Mike, Sharon, and Kaila to six Key West drinking and dining spots. You’ll taste five full-size craft cocktails, enjoy two food tastings, hear local stories, and finish with a taco at Garbo’s Grill.

“Wonderful experience with Rose.Such a fun and informative time.Would highly recommend the different bars and different cocktails were fun to taste. The last one with the Flaming Zombie was delicious.The food nibbles were very good also.Loved the Asian Cauliflower”

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6.Reef Snorkeling with Drinks and Sunset Option

★★★★★★★★★★4.4 · 419 reviews · 3 hours · from $34

Sail from Opal Key Marina to Key West’s living coral reef aboard Fury’s 65-foot catamaran. A professional crew provides gear and instruction, with 30 to 60 minutes in the water. Choose morning mimosas, afternoon margaritas, or a sunset rum punch sail.

“The boat was lovely and the crew was fun, and friendly. The snorkeling was good with the best snorkeling lesson I’ve ever received in all my years snorkeling! I would highly recommend this trip and it was the perfect amount of time as well! Thanks for a great time!”

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7.Key West Afternoon Reef Snorkeling with Open Bar

★★★★★★★★★★4.5 · 419 reviews · 3 hours (approx.) · from $59

Board the Sandie Cat at 201 William Street for a guided afternoon snorkel on Key West’s coral reef. The crew provides equipment and instruction, then serves unlimited beer, wine, champagne, rum runners, margaritas, and mixed drinks after you leave the water. Expect about an hour of cruising each way.

“Captain and crew were friendly, ride out and in were both nice and smooth. Beautiful day on the water. Not much to see besides fish and coral but worth it to spend the day on the water with family and a good time”

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8.Key West Signature Sunset Cruise with Open Bar, Food & Music

★★★★★★★★★★4.5 · 418 reviews · 2 hours · from $79

Sail from Key West’s historic seaport aboard the three-deck Sandie Cat for a two-hour sunset cruise. You get unlimited basic drinks, light appetizers, live music, and room to move around. The crew may invite you to help raise the sails or take a turn at the wheel.

“What a blast!!!!!! So beautiful, great music, great staff, and an all around amazing time! Definitely recommend for a true key west experience!”

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

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

Join a 2.5-hour evening walk through Key West’s Duval Street and Historic Seaport. A local guide such as Sarah, Laurie, Brian, or Garrett leads you to five bars, where you choose a domestic beer or mixed drink, including options such as a pina colada or Caribbean Breeze. You must be 21 or older.

“Great host, great value! This tour is a good chance to visit some establishments that you may not have discovered on your own. Highly recommended!”

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10.3-Hour Afternoon Reef Snorkel with Drinks

★★★★★★★★★★4.3 · 351 reviews · 3 hours · from $59

Cruise from 201 William Street to Key West’s offshore coral reef with Captain Anna and an English-speaking crew. You’ll receive snorkel gear, safety help, and time in the water, then enjoy drinks on the sail back. Bring a towel, sunscreen, cash, and extra clothes.

“This was a super fun experience. And the boat staff were really funny and sweet. Highly recommend”

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11.Key West 6-Hour Party Boat Fishing Trip – Affordable Reef Fishing

★★★★★★★★★★4.5 · 325 reviews · 6 hours (approx.) · from $85

Spend about six hours fishing Key West’s offshore reefs aboard Gulfstream Fishing’s party boat. The captain and first mates, including Ethan, Ryan, Bryan, and Joe on various departures, help with bait, hooks, and technique. Bait, a fishing license, restrooms, and free parking are included. Rod rental costs $5.

“The staff is incredible! Very helpful, knowledgeable & fun! Made the trip so enjoyable. Plus we caught lots of fish!”

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12.Key West Signature Sunset Sail with Live Music, Open Bar & Food

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72

Board the Sandie Cat at 201 William Street for a two-hour Key West sunset sail with live music, panoramic water views, unlimited well drinks, beer, wine, champagne, and light appetizers. Captain Anna has earned praise for her calm, friendly presence. Children may join, so expect a mixed crowd rather than an adults-only party.

“This sunset cruise was the best. Fabulous crew and the boat was gorgeous. Great time and great sunset”

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13.Afternoon Reef Snorkel Tour with Open Bar

★★★★★★★★★★4.3 · 268 reviews · 3 hours · from $59

Spend three hours aboard a Sebago catamaran, with instruction, reef snorkeling, and a return sail with cocktails, beer, wine, and soda. The captain chooses the site based on wind and water conditions, while the crew helps first-time snorkelers get comfortable.

“Amazing experience snorkeling with the Sebago team. Beautiful reef with multiple fishes, a shark and even a sea turtle. A light delicious lunch and drinks appreciated on top of that.”

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14.Sunset Dinner Cruise with Open Bar & Live Music

★★★★★★★★★★4.5 · 228 reviews · 2 hours · from $92

Spend two hours aboard The Party Cat on a Key West harbor cruise with a tropical buffet, open bar, and live music on the upper deck. You will see the sunset over the Gulf of Mexico, hear performers such as Dante, and enjoy a lively evening near 201 William Street.

“Fantastic entertainment! Well organized. Good food and great drinks. Would definitely do it again!”

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

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

Sail from Key West Historic Seaport aboard a classic schooner for two relaxed hours. Captain Joe, Josh, and crew members such as Cristina, Michael, and Vitali have helped make this a polished small-group outing, with cocktails, wine, beer, champagne, snacks, and wide sunset views.

“It was everything I expected and more. This was my first sunset experience on a schooner and well worth it. Captain Joe and 1st Mate, Michael were great! It was cool to see them open the sails. They were both so attentive to everyone’s needs. The cocktails and appetizers were great. It’s a FULL bar just as advertised. Captain Joe took the boat where there wasn’t another boat between you and the perfect sunset where we were fortunate enough to see the green flash off the water at the sun disappeared. I will take this sunset experience again the next time I’m in town. By far the best sunset cruise…”

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