The colorful island of Key West excels at drinking tours, offering both quality and variety. The standout options combine sightseeing with socializing – exactly what savvy travelers want from a Florida Keys experience.
Our favorite picks include the sunset sail tours, which pair premium open bars with local appetizers while showcasing the island’s famous sunsets. For history buffs, the guided pub crawls through Old Town reveal haunted tales between stops at historic watering holes. The reef snorkel cruises cleverly mix underwater exploration with topside refreshments, while the intimate tiki boat tours let small groups customize their own floating happy hour.
Let’s explore the best drinking tours that capture Key West’s laid-back spirit…
Key Points
- The Original Key West Pub Crawl offers a 2.5-hour guided tour visiting five bars with a 90% recommendation rate and included drinks.
- The Duval Street Pub Crawl provides a 4.5/5-rated experience with five cocktails, wheelchair accessibility, and a flexible cancellation policy.
- The Haunted Pub Crawl and Bone Island Haunted Pub Crawl offer intimate, spooky experiences exploring Key West’s paranormal history at local bars.
- Private Tiki Bar Party Boats and Private Sandbar Cruises allow groups of up to six to customize their drinking experiences on the water.
- The Sunset Sip and Sail tour accommodates 75 travelers, featuring live music and an open bar to enhance the sunset experience.
Classic Key West Schooner Sunset Sail With Full Open Bar
Adventurers seeking a tranquil yet enchanting sunset sail in Key West need look no further than the Classic Key West Schooner Sunset Sail With Full Open Bar.
This highly-rated tour offers an intimate experience for a maximum of 22 travelers, with a 98% recommendation rate from past visitors. The classic schooner sails past Mallory Square and Navy Mole, allowing guests to hoist the sails with the friendly, knowledgeable crew.
Unlimited beer, wine, champagne, soft drinks, and water, along with a full liquor bar and delectable hors d’oeuvres, ensure a delightful journey.
With an overall rating of 4.9 out of 5, this sunset sail stands out as a must-do activity in Key West.
Read our full review: Classic Key West Schooner Sunset Sail With Full Open Bar Review
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Key West: Afternoon Reef Snorkel Tour With Live Music & Bar
Snorkeling the only living coral barrier reef in North America is a captivating way to explore Key West’s vibrant marine life.
The Afternoon Reef Snorkel Tour offers a 3-hour adventure, taking guests on a catamaran ride to the reef where they can marvel at colorful sea creatures.
With experienced instructors providing guidance, even beginners can enjoy the underwater world.
Relax on the sun deck and indulge in an open bar with cocktails, beer, wine, and soda.
Reviews praise the friendly guides and fantastic crew, making this tour a great value for money.
Whether you’re seeking an educational experience or just want to unwind, this reef snorkel tour is a must-do activity in Key West.
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Key West Sunset Sail With Full Bar, Live Music and Hors Doeuvres
As the sun dips below the horizon, Key West offers a captivating alternative to the reef snorkel tour – the Sunset Sail with Full Bar, Live Music, and Hors D’oeuvres.
This 60-foot catamaran cruise provides stunning views of Key West landmarks and a front-row seat to the captivating sunset. Theres some good a selection of hors d’oeuvres and an all-inclusive bar while local musicians provide live entertainment.
With a maximum capacity of 80 travelers, the cruise fosters a casual, fun atmosphere, perfect for dancing, singing, and socializing.
Despite some suggestions for more diverse snack options and better wine selections, the majority of customers highly recommend this memorable Key West experience.
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Key West: Sunset Dinner Cruise With Open Bar & Live Music
For those seeking an unforgettable evening in Key West, the Sunset Dinner Cruise with Open Bar & Live Music offers a captivating experience.
This 2-hour cruise features panoramic views of the sunset over the Gulf of Mexico, a tropical food buffet, and an open bar serving a variety of beverages. Guests can enjoy live music on the upper deck while cruising.
With an overall rating of 4.3/5 based on 154 reviews, the activity is praised for its food quality, service, and celebratory atmosphere.
The cruise includes hotel pickup and drop-off, and reservations can be made without upfront payment, with free cancellation up to 24 hours in advance.
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Key West Schooner Sunset Sail With Bar & Hors Doeuvres
The Key West Schooner Sunset Sail with Bar & Hors d’oeuvres offers a captivating 2-hour cruise along the picturesque waters surrounding Key West.
This highly-rated experience, with 577 reviews and a 4.9/5 star rating, takes guests aboard a 68-person capacity schooner for an unforgettable sunset journey.
Included in the $116.10 per person price are complimentary drinks, such as beer, wine, and champagne, as well as individually plated hors d’oeuvres.
Guests can admire the stunning views and enjoy the attentive service provided by the crew.
With easy check-in, free cancellation, and a convenient location near public transportation, this sunset sail is an excellent choice for those seeking a relaxing and indulgent evening in Key West.
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Key West: Sunset Snorkel Cruise With Draft Beer & Wine
Snorkeling the world’s third largest coral barrier reef at sunset is the highlight of this immersive 3-hour Sunset Snorkel Cruise in Key West. Priced from $69.95 per person, the cruise includes snorkeling gear, safety equipment, soft drinks, water, draft beer, and wine.
After snorkeling, guests can enjoy unlimited cold draft beer and wine while taking in panoramic views of the sunset over the Gulf of Mexico. The relaxing boat ride back features music, and the cruise provides hotel pickup and drop-off, as well as free cancellation up to 24 hours in advance.
With an overall rating of 4.7/5 from 47 reviews, this tour is suitable for couples, families, groups, and solo travelers.
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Original Key West Pub Crawl: the Best Bars With Free T-Shirt
Explore Key West’s vibrant bar scene on the Original Key West Pub Crawl, a 2.5-hour guided tour that takes visitors to five of the city’s popular establishments.
With a 90% traveler recommendation and 329 reviews, this tour is known for its lively atmosphere, knowledgeable guides, and engaging experiences. Guests will sample domestic beers or mixed drinks at each stop and can enjoy specialty drinks like frozen piña coladas.
The tour includes a free souvenir t-shirt and is accessible to wheelchair users. While not recommended for pregnant travelers or those with serious medical conditions, the Original Key West Pub Crawl offers a fun and immersive way to experience the city’s historic seaport and Duval Street.
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Key West: Sunset Sailing Trip With Open Bar, Food and Music
For those seeking a more relaxed and scenic way to experience Key West’s vibrant nightlife, the Key West: Sunset Sailing Trip with Open Bar, Food and Music offers an unparalleled opportunity.
Lasting 2 hours, this excursion aboard the spacious Sandie Cat catamaran allows visitors to soak in the stunning sunset while indulging in an open bar, appetizers, and live music.
With an overall rating of 4.5/5 from 228 reviews, the trip is a must for first-time visitors and locals alike.
At $69.95 per person, the experience provides excellent value, as guests can enjoy unlimited drinks, a selection of hors d’oeuvres, and the chance to participate in sailing the vessel.
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Key West Sunset Snorkel With Unlimited Draft Beer & Wine
The Key West Sunset Snorkel with Unlimited Draft Beer & Wine offers an unforgettable way to experience the natural beauty of the Florida Keys.
With over 111 reviews and a Badge of Excellence, this tour combines a sunset sail and snorkeling at a nearby coral reef. Guests can relax with unlimited draft beer and wine as they cruise the Atlantic Ocean, enjoying the stunning views and social atmosphere.
The snorkeling equipment is provided, and the friendly and knowledgeable crew, like Captain Chuck and Dante, ensure a memorable experience.
While some guests have reported minor issues with the check-in process and drink availability, the overall consensus is that this tour is a “must do” in Key West.
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Key West: Bone Island Haunted Pub Crawl
Enjoy Key West’s sinister past on the Bone Island Haunted Pub Crawl, a captivating 2-hour guided tour that takes you to three of the island’s most haunted watering holes.
Led by a professional ghost host, you’ll discover the history of cursed treasure, voodoo, murder, and unexplained deaths that haunt this island.
Priced at $32.20 per person, the tour includes a souvenir t-shirt and access to purchase cocktails.
With a 4.5/5 rating from 24 reviews, this popular activity is likely to sell out, so book your spot now and pay later.
After the tour, explore Key West’s vibrant downtown area at your leisure.
Read our full review: Key West: Bone Island Haunted Pub Crawl Review
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Key West Tiki Bar Sunset Cruise (By the Seat)
Travelers seeking a serene sunset experience away from the bustling crowds of Mallory Square can embark on the Key West Tiki Bar Sunset Cruise.
Accommodating a maximum of six people, this small-group cruise offers a personal sunset viewing away from the typical tourist spots. Passengers can bring their own beverages and enjoy snacks while the USCG-certified captain navigates the Key West harbor, providing insightful commentary.
With an overall rating of 4.8 stars and positive guest reviews praising the captains’ knowledge and engaging narratives, this cruise is an excellent choice for those wanting a unique and tranquil sunset experience in Key West.
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Key West: Private Tiki Bar Party Boat & Mini Sandbar
Consistently, guests seeking a private and lively tiki bar experience in Key West can embark on the Key West: Private Tiki Bar Party Boat & Mini Sandbar excursion.
Priced at $403.13 for up to 6 participants, this 2-hour private cruise allows visitors to sail to a local swimming hole, relax on a floating mat, and enjoy drinks and snacks while listening to music.
The experience includes a tiki boat, fuel, a Coast Guard-approved captain, a cooler with water, and a Bluetooth stereo.
Customers have praised the knowledgeable captain and enjoyable atmosphere, making this tour suitable for couples, friends, solo travelers, and families.
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Key West Tiki Bar Boat Cruise to a Popular Sand Bar
The Key West Tiki Bar Boat Cruise to a Popular Sand Bar offers a unique and exciting way for visitors to experience the natural beauty of Key West.
With a 95% recommendation rate and a Badge of Excellence, this 4-hour tour provides guests with an array of amenities, including ice, cups, bottled water, and even a restroom on board.
Travelers can enjoy alcoholic beverages (BYOB) and snacks while cruising to the popular sandbar.
The tour’s experienced captains, such as Captain Jimmy, Captain Zappa, and Captain Madison, ensure a memorable and enjoyable experience.
While some guests have reported booking discrepancies, the company remains committed to enhancing the overall experience for all visitors.
Read our full review: Key West Tiki Bar Boat Cruise to a Popular Sand Bar Review
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Key West: 2.5-Hour Duval Street Pub Crawl
For those seeking a lively night out in Key West, the 2.5-Hour Duval Street Pub Crawl offers an exhilarating way to experience the island’s vibrant bar scene.
Priced at $42.95 per person, the tour includes entrance fees, five cocktails, a guided exploration, and a souvenir t-shirt. Participants will visit five renowned pubs known for their festive atmosphere, enjoying live music and Caribbean-inspired drinks.
The tour is wheelchair accessible and features a flexible cancellation policy, allowing for full refunds up to 24 hours in advance.
With an overall rating of 4.5/5 based on 50 reviews, this pub crawl promises an unforgettable experience filled with socializing, entertainment, and a glimpse into Key West’s lively nightlife.
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Dinghy Drinking Tour Through Key West Waters
Departing from Garrison Bight Marina, the Dinghy Drinking Tour takes adventurous travelers on an intimate journey through Key West’s picturesque waterways.
Navigating narrow mangrove tunnels, the small-group tour offers a unique experience, combining bar hopping with scenic exploration. Participants can expect to visit two or three waterfront establishments, while keeping an eye out for local wildlife like manatees and nurse sharks.
With a licensed captain at the helm, the tour promises a fun and engaging experience, as confirmed by the 96 positive reviews and 98% traveler recommendation.
Whether looking for a different way to explore Key West or simply enjoy a day of drinking and socializing, this tour delivers.
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Key West Tour and Coral Reef Snorkeling With Open Bar
Exploring Key West’s vibrant culture and captivating underwater world, the Key West Tour and Coral Reef Snorkeling with Open Bar promises an unforgettable experience.
Priced at €94.92 per person, this 14-hour tour includes round-trip transportation from Miami, as well as a guided exploration of the Florida Keys and a 3-hour snorkeling adventure at the Key West Coral Reef.
Travelers can enjoy unlimited drinks on the catamaran and free time to discover Key West’s landmarks, museums, and outdoor cafés.
With a 4/5 customer rating, this tour offers a perfect blend of sightseeing, snorkeling, and indulgence, making it a must-try for those seeking to enjoy the essence of Key West.
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Sunset Sip and Sail Key West With Open Bar and Live Music
The Sunset Sip and Sail Key West with Open Bar and Live Music offers a captivating experience that seamlessly blends the vibrant essence of Key West with the serene beauty of a sunset cruise.
Boasting 244 reviews and a Badge of Excellence, this top-rated excursion accommodates a maximum of 75 travelers and departs from 201 William St, Key West, FL.
Revelers can indulge in an unlimited open bar serving draft beer, wine, champagne, mixed drinks, and more, while savoring appetizers like Jamaican jerk chicken sliders and enjoying live music.
With a stunning new catamaran, the Sunset Sip and Sail promises an unforgettable evening on the water, complete with breathtaking sunsets and potential wildlife sightings.
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Key West: Schooner Day Sail With Onboard Bar
Visitors can set sail aboard the elegant Schooner America 2.0 for a captivating 1.5-hour cruise around the Florida Keys. Priced from $73.10 per person, the experience allows guests to sail past iconic landmarks like Fort Zachary Taylor and Mallory Square.
The 105-foot sailboat features 3,600 square feet of sail and boasts teak decks and mahogany trimmings. Guests can enjoy a beverage package with two alcoholic drinks for those 21 and older, as well as complimentary soft drinks and water.
With a high overall rating of 4.7/5, the cruise is praised for its professionalism, beautiful boat, and exceptional service.
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Key West Haunted Pub Crawl and Ghost Tour With Free T-Shirt
For those captivated by Key West’s haunting past, the Key West Haunted Pub Crawl and Ghost Tour offers an immersive experience into the island’s paranormal history.
Over the course of two hours, visitors will explore eerie bars located in haunted mansions and a former morgue, while a local guide regales them with tales of Key West’s spooky past.
Highlights include stops at the Hard Rock Café, Captain Tony’s Saloon, and Tattoos & Scars Saloon.
With a maximum capacity of 25 travelers, the tour provides an intimate and engaging group experience.
Participants must be 21 or older and prepared to enjoy some drinks (at their own expense) while delving into Key West’s “Bone Island” legacy.
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Key West: Haunted Pub Crawl Walking Tour
Key West’s haunted past comes alive on the Haunted Pub Crawl Walking Tour. This 2-hour tour takes visitors through the island’s spookiest spots, including famous haunted pubs and restaurants.
For $29.99, participants can explore the dark history of Key West while enjoying drinks. The tour is limited to 9 people, providing a unique perspective as a local guide shares tales of demonic dolls and tragic events.
Highlights include visits to Captain Tony’s Saloon, the Wine-O Bar & Lounge, and the Key West Theater. With an overall rating of 4.2/5, the tour offers an informative and fun experience for those aged 21 and up.
Comfortable shoes and weather-appropriate clothing are recommended.
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Key West Cocktail Cruise Adults Only Sunset Cruise With Open Bar
The Key West Cocktail Cruise offers an adults-only sunset experience on a 47-foot catamaran. Guests can relax and take in the scenic views while enjoying an open bar featuring South Florida craft beer, California wine, and hand-crafted cocktails.
The live commentary from the captain provides local stories and insights, and there’s an opportunity for professional photography. With a 96% recommendation rate from 143 reviews and a 4.9/5 rating, this 2-hour cruise is a popular choice.
Guests can bring their own snacks, but food isn’t included. While some have noted concerns about hidden fees and communication, the overall experience is described as memorable, with many praising the crew’s hospitality and knowledge.
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Miami: Key West Boat Tour W/ Optional Snorkeling & Open Bar
Travelers seeking a full-day adventure can embark on the Miami: Key West Boat Tour with Optional Snorkeling and Open Bar. Priced from $33 per person, the tour offers a round-trip journey by air-conditioned bus, with 4 hours each way.
In Key West, guests enjoy 1 hour of free time, followed by 3 hours of sightseeing, snorkeling, and sailing. The snorkeling experience allows them to explore the largest coral ecosystem in the mainland US, spotting marine life like barracudas, turtles, and vibrant fish.
With an open bar option, the tour provides a fun-filled day with mixed reviews on transportation comfort and guide service.
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Key West Afternoon Reef Snorkeling With Open Bar
Adventurers seeking a thrilling reef snorkeling experience in Key West can embark on the Afternoon Reef Snorkeling with Open Bar tour. Priced from $54.95 per person, this 3-hour excursion allows visitors to explore the world’s 3rd largest living coral reef, teeming with vibrant marine life.
Aboard Key West’s newest and most luxurious snorkel boat, guests will receive all necessary equipment and expert guidance from experienced instructors. After snorkeling, participants can enjoy an open bar with unlimited draft beer, rum runners, margaritas, wine, and more.
With a maximum capacity of 70 travelers and a 4.5-star rating from 307 reviews, this tour provides an unforgettable reef adventure combined with an open-bar experience.
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Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat
For those seeking a truly unique and immersive experience in Key West, the 4-Hour Private Sandbar Cruise on a Tiki Bar Boat offers a delightful blend of relaxation and adventure.
Priced at $564.38 per group (up to 6 participants), this private cruise allows guests to explore the turquoise waters of the Florida Keys while partying on an authentic Tiki Bar Boat.
Led by a US Coast Guard licensed captain, the tour includes opportunities to spot marine life, enjoy bottled water and ice, and relax on a floating mat or foam noodles.
With a full restroom on board and a Bluetooth stereo, this socially distanced experience promises a memorable day in paradise.
Read our full review: Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat Review
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Dolphin Morning Watching & Snorkeling + Open Bar + 1 Day Hop-On Hop-Off Fun
The Dolphin Morning Watching & Snorkeling + Open Bar + 1 Day Hop-On Hop-Off Fun in Key West offers an exhilarating opportunity to get up close with the marine life of the Florida Keys.
This combo tour includes dolphin watching, snorkeling in one of the world’s largest reefs, and a visit to the Sails and Rails Museum. Participants can also enjoy a Conch Train ride and explore landmarks like the Ernest Hemingway Home and Museum.
With an open bar and a maximum of 80 travelers, this tour provides a relaxing and enjoyable experience. Priced at $149.99 per person and with a 5.0 rating based on one review, it’s a top choice for those seeking a unique and memorable day in Key West.
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Sum Up
Key West offers a variety of drinking tours that cater to different interests. From sunset sails with open bars to reef snorkeling with live music, there’s something for all. Whether you’re looking to relax with a cocktail or explore the waters, these tours provide a unique and memorable experience in the vibrant Floridian city.