Key West’s drinking tours combine tropical scenery with convivial bar-hopping opportunities.
The standout options include well-organized sunset cruises and historic pub crawls. On the water, I’m especially fond of the Sunset Sip and Sail Cruise – it’s perfectly timed and less crowded than others.
The catamaran tours with open bars offer good value, serving quality drinks alongside tasty appetizers.
The Original Key West Pub Crawl earns my recommendation for its thoughtful selection of authentic local bars and generous five-drink inclusion.
It’s the smartest way to experience the island’s historic drinking spots while learning colorful local stories.
Let’s examine the finest drinking tours in Key West, ranked by value and experience.
Key Points
- The Original Key West Pub Crawl offers a 2.5-hour tour with visits to five iconic bars and five free drinks included.
- The Haunted Pub Crawl and Ghost Tour explores Key West’s haunted past with a maximum group size of 25 for personalized storytelling.
- The Dinghy Drinking Tour provides a unique bar crawl experience beyond the traditional Duval Street, with a guided boat ride through picturesque waterways.
- The Key West Haunted Pub Crawl Walking Tour is a 2-hour tour that explores the city’s spooky past, starting at 8 PM and ending at Capt Tony’s Saloon.
- The Key West Private Tiki Bar Party Boat & Mini Sandbar offers a 2-hour tour featuring a lively Tiki bar experience on a private boat.
Key West Sunset Sail With Full Bar, Live Music and Hors Doeuvres
A 70-foot catamaran awaits you for this Key West sunset sail, offering 1,500 feet of deck space to escape the crowds and take in the breathtaking views.
With 2,887 reviews and a 92% traveler recommendation, this sunset cruise delivers an exceptional experience.
Enjoy complimentary food and drinks, including hearty appetizers, peel-and-eat shrimp, and a full liquor bar.
Live music from local musicians creates a lively atmosphere as you sail to the best sunset viewing spot and watch the sun set and moon rise.
Arrive 30 minutes early for check-in, as this tour is likely to sell out and not wheelchair accessible.
Read our full review: Key West Sunset Sail With Full Bar, Live Music and Hors Doeuvres Review
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Classic Key West Schooner Sunset Sail With Full Open Bar
Set out on a Classic Key West Schooner Sunset Sail With Full Open Bar, offering an intimate and unforgettable experience.
This highly-rated tour accommodates a maximum of 22 travelers, ensuring a personalized atmosphere. Enjoy unlimited beer, wine, champagne, and cocktails, along with delectable appetizers, as you sail into the sunset.
The friendly and attentive crew will enhance your journey, providing opportunities to interact and learn about sailing. Reviewers praise the peaceful ambiance, beautiful scenery, and exceptional service.
Although some consider the $109 per person cost a bit high, the quality of the experience is widely acknowledged as justifying the price.
This must-do activity in Key West is sure to create lasting memories.
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Sunset Sip and Sail Key West With Open Bar and Live Music
For those seeking a quintessential Key West sunset experience with an open bar and live music, the Sunset Sip and Sail cruise is a must-try.
This top-rated tour offers beautiful views and a lively ambiance, catering to a maximum of 75 travelers. Enjoy unlimited well-mixed drinks, from draft beer to rum runners, along with a selection of appetizers.
The live music performance adds to the overall experience, allowing you to dance the evening away.
With a convenient meeting point, smooth check-in, and positive customer reviews, this sunset cruise is an excellent choice for those looking to make the most of their time in Key West.
Read our full review: Sunset Sip and Sail Key West With Open Bar and Live Music Review
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Key West Schooner Sunset Sail With Bar & Hors Doeuvres
Climb aboard the elegant Schooner as it sets sail on a captivating 2-hour Key West sunset cruise.
You’ll be treated to complimentary beer, wine, champagne, and soda, as well as individually plated hors d’oeuvres.
With a maximum of 68 travelers on board, you’ll enjoy an intimate experience with attentive crew.
Take in the beautiful vessel, relax, and savor the excellent views of the Florida Keys.
While some guests have noted concerns about service and noise levels, the majority found this a superb experience worth repeating.
Whether you’re celebrating the holidays or ringing in the new year, this sunset sail offers a delightful way to experience Key West’s stunning coastline.
Read our full review: Key West Schooner Sunset Sail With Bar & Hors Doeuvres Review
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Original Key West Pub Crawl: the Best Bars With Free T-Shirt
Seeking a lively night out in Key West? The Original Key West Pub Crawl has you covered.
This highly-rated 2.5-hour tour takes you to five iconic bars, with five free drinks and a free souvenir t-shirt included. Led by experienced local guides, you’ll explore Whitehead Street, the Historic Seaport, and the legendary Duval Street, discovering the best watering holes along the way.
From frozen piña coladas at Rick’s Key West to Caribbean Breeze cocktails, the diverse drink menu caters to all tastes.
With a maximum of 35 participants, this wheelchair-accessible tour offers an intimate and engaging experience.
Read our full review: Original Key West Pub Crawl: the Best Bars With Free T-Shirt Review
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Key West Sunset Snorkel With Unlimited Draft Beer & Wine
Combine the thrill of a sunset sail and the wonder of snorkeling in one unforgettable tour with the Key West Sunset Snorkel With Unlimited Draft Beer & Wine.
Relax with music as you cruise the Atlantic Ocean, then dive into a nearby coral reef equipped with provided snorkeling gear.
Socialize with fellow travelers while taking in the breathtaking views and sipping on unlimited draft beer and wine.
This highly-rated tour offers excellent value, with complimentary beverages, gratuities, and free cancellation up to 24 hours in advance.
Departs from and returns to the convenient meeting point.
While not wheelchair accessible, children are welcome with adult accompaniment.
An ideal way to experience Key West’s natural beauty and vibrant social scene.
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Key West Haunted Pub Crawl and Ghost Tour With Free T-Shirt
As night falls in Key West, you can embark on an unforgettable journey through the city’s haunted past on the Key West Haunted Pub Crawl and Ghost Tour.
This 2-hour excursion takes you to notable locations like the Hard Rock Café and Captain Tony’s Saloon, where you’ll hear spooky tales while enjoying drinks at your own expense.
Led by a professional local guide, the tour explores Key West’s haunted sites and stories in the historic Old Town.
With a maximum group size of 25, you’ll enjoy a personalized experience and receive a souvenir t-shirt.
The tour is wheelchair accessible and service animals are allowed, making it an inclusive option for all.
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Dinghy Drinking Tour Through Key West Waters
For an adventurous twist on the classic Key West bar crawl, embark on the Dinghy Drinking Tour through the city’s picturesque waterways.
This 5-star rated tour takes you on a guided boat ride, where you can relax with drinks as you explore mangroves and spot marine life.
With a knowledgeable and humorous captain, you’ll visit local bars and experience Key West beyond Duval Street.
While the pickup location may vary, this tour offers a unique way to enjoy the city’s sights and flavors.
Just be prepared for some physical agility, as navigating low bridges and climbing ladders is required.
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Key West Tiki Bar Boat Cruise to a Popular Sand Bar
Set out on a unique tiki bar boat experience in Key West with the Key West Tiki Bar Boat Cruise to a Popular Sand Bar.
This private tour avoids overcrowding while offering the chance to see marine life and relax at a picturesque sandbar. The knowledgeable captain provides insights about the local area and wildlife.
Enjoy BYOB alcoholic beverages, snacks, and bottled water onboard the vessel’s restroom-equipped tiki bar. Though not recommended for travelers with back issues or wheelchair users, most can participate.
With a 5-star rating and 96% recommendation, this tour provides a memorable, fun-filled day on the water.
Read our full review: Key West Tiki Bar Boat Cruise to a Popular Sand Bar Review
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Key West Tiki Bar Sunset Cruise (By the Seat)
Take in the stunning Key West sunset on the Key West Tiki Bar Sunset Cruise (by the seat). This 2-hour cruise departs from Garrison Bight Marina and is BYOB, allowing you to bring your own drinks and snacks.
The USCG-certified captain will guide your intimate group of up to 6 travelers, sharing knowledgeable commentary and interesting facts. Enjoy the relaxing atmosphere as you sip your beverage and admire the vibrant colors of the sunset.
Though the cruise isn’t wheelchair accessible, most travelers can participate. Be sure to arrive 15 minutes early, as parking is free.
With 94% of 128 reviews recommending this tour, it’s an excellent way to experience the beauty of Key West from the water.
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Key West Cocktail Cruise Adults Only Sunset Cruise With Open Bar
If you’re seeking an adults-only sunset cruise in Key West with an open bar, the Key West Cocktail Cruise is an excellent choice.
This 2-hour cruise aboard a 47-foot catamaran offers stunning views of the Floridian coast and unlimited South Florida craft beer, California wine, and hand-crafted cocktails.
The knowledgeable and entertaining crew provide live commentary, and a professional photographer guide captures the experience.
While the open bar and personalized service due to the smaller group size are highlights, be aware of potential extra charges for fuel and communication issues regarding weather-related cancellations.
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Key West Afternoon Reef Snorkeling With Open Bar
For an afternoon of underwater exploration and refreshing libations, the Key West Afternoon Reef Snorkeling with Open Bar is an unparalleled experience.
With a Badge of Excellence and 297 enthusiastic reviews, this 3-hour tour promises a luxurious vessel, expert guides, and the world’s 3rd largest living coral reef.
Snorkel amid vibrant marine life, then enjoy an open bar with beer, cocktails, and a complimentary lunch.
While not wheelchair accessible, most travelers can participate.
Reviewers highlight the crew’s attentiveness, equipment quality, and overall fun factor, though some note limited fish sightings.
Operated by Sunset Watersports, this tour offers a memorable Key West adventure for those seeking both aquatic exploration and drinking entertainment.
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Key West Haunted Pub Crawl Walking Tour
The Key West Haunted Pub Crawl Walking Tour offers a captivating exploration of the city’s spooky past.
This 2-hour tour starts at 8 PM, meeting across from Shots & Giggles before winding through historic pubs and ending at Capt Tony’s Saloon.
Led by knowledgeable guides like Kris, Chris, Cheryl, and Maggie, you’ll learn about Key West’s ghostly legends and enjoy alcoholic beverages along the way.
While some guests wished for deeper access to homes and bars, the tour’s focus on storytelling and local history generally receives positive reviews.
At $29.99 per person for a maximum of 20 travelers, the Key West Haunted Pub Crawl provides a fun and informative way to experience the city’s haunted side.
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Key West Sand Bar, Sunset and Eco Trip
Key West offers a diverse range of experiences beyond its haunted history. One such adventure is the Key West Sand Bar, Sunset and Eco Trip.
This private excursion from Island to Island Charters takes you to a stunning sand bar, where you can snorkel, sunbathe, and explore the ecological wonders of the area.
With a 5.0 average rating from 8 reviews, the trip includes use of snorkeling equipment, bottled water, and transportation.
Highlights include spotting dolphins, sharks, and turtles.
At just under €864 for a group of up to 6, this eco-friendly tour is an absolute must-do during your time in Key West.
Read our full review: Key West Sand Bar, Sunset and Eco Trip Review
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2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West
Seeking a relaxing and scenic way to end your day in Key West? Consider the 2-Hour Private Sunset Cruise on a Tiki Bar Boat.
This USCG-certified experience boasts a 90% recommendation rate and a Badge of Excellence. Cruise past iconic landmarks like Sunset Pier and Key West Historic Seaport while sipping BYOB drinks and enjoying the sunset.
The onboard amenities include bottled water, a blender, and a Bluetooth stereo. While some guests desired a more party-like atmosphere, others appreciated the informative captain and the tranquil ambiance.
Be prepared for potential motion sickness due to the boat size and water conditions. This cruise offers a unique way to unwind and take in the beauty of Key West.
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Key West: Dolphin Watching Cruise & Snorkeling Unlimited Beer & Soda
Enjoy the marine wonders of Key West with the Dolphin Watching Cruise & Snorkeling Unlimited Beer & Soda.
This 89.99 USD tour takes you on a 25-person excursion to spot dolphins and snorkel the vibrant waters. Expect a knowledgeable crew, free use of snorkeling gear, and unlimited beer and soda.
Though the weather may impact visibility, previous guests report seeing dolphin pods, including mothers and calves. The snorkeling at alternative sites like sponge gardens still provides unique encounters.
With a moderate fitness level required, this tour offers an engaging way to explore Key West’s coastal ecosystem while enjoying refreshments.
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Key West: Private Tiki Bar Party Boat & Mini Sandbar
Set out on a lively Tiki bar experience aboard a private boat in the heart of Key West.
This 2-hour tour takes you on a cruise to a local swimming hole, where you can relax on a floating mat and enjoy the cooler filled with ice and bottled water.
The Tiki boat features a thatched roof, Bluetooth stereo, and a walk-in bathroom.
For up to 6 participants, the tour costs $403.13 and is led by a live English-speaking guide.
Flexible booking allows you to reserve now and pay later, with free cancellation up to 24 hours in advance.
Don’t miss this unique opportunity to drink and party on the waters of Key West.
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Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat
Discover the stunning turquoise waters of Key West and the Florida Keys on a 4-hour private sandbar cruise aboard an authentic Tiki Bar Boat.
With a group of up to 6 people, you’ll party in paradise while socially distancing. Spot rays, turtles, fish, and dolphins as you explore the vibrant marine life.
The U.S. Coast Guard licensed captain will provide bottled water, a Bluetooth stereo, and a full restroom. Bring your swimwear, towel, and any food or drinks you’d like.
At $535.90 per group, this is an affordable way to experience the Keys in style.
With high marks for transportation and value, it’s an adventure you won’t want to miss.
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Key West: Multiple Water Sports Excursion With Lunch & Beer
Explore a thrilling array of water sports during this 6-hour excursion in Key West. For $178.95, you’ll have the chance to try 12 different activities, including parasailing, jet skiing, and snorkeling.
Enjoy a grilled lunch buffet and free draft beer on the return cruise. The meeting point is at 201 William Street, and you’ll be guided by a friendly crew, including Captain Rachel, Captain Clint, and bartender Dave.
Reviews highlight the exceptional lunch quality and the crew’s safety guidance. With an overall rating of 4.2/5, this excursion offers great value and a fun-filled day on the water.
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Miami: Key West Boat Tour W/ Optional Snorkeling & Open Bar
For your day trip from Miami to Key West, you can opt for a boat tour that offers an array of exciting activities.
The 18-hour tour includes round-trip transportation, with a 4-hour bus ride each way.
In Key West, you’ll have 1 hour of free time and 3 hours to snorkel the largest coral ecosystem in the mainland US, spotting marine life like barracudas and sea turtles.
If you select the open bar option, you can enjoy drinks throughout the journey.
The tour offers a good value, with savings of up to 33% and a flexible cancellation policy.
However, past customers have had mixed experiences with transportation comfort and guide service.
Read our full review: Miami: Key West Boat Tour W/ Optional Snorkeling & Open Bar Review
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Key West Tour and Coral Reef Snorkeling With Open Bar
This comprehensive tour offers a unique opportunity to experience the vibrant culture and stunning natural beauty of Key West.
For €94 per person, you’ll enjoy a 14-hour adventure that includes round-trip transportation from Miami, free time to explore Key West, and a 3-hour snorkeling excursion at the Key West Coral Reef.
With English and Spanish-speaking guides, air-conditioning, and unlimited drinks after your swim, this tour provides a hassle-free way to discover the Florida Keys.
Just remember to bring comfortable attire, sun protection, and your passport or ID.
Whether you’re seeking history, nature, or simply a day of relaxation, this tour has a lot to offer.
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Key West: Sunset Dinner Cruise With Open Bar & Live Music
Enjoy a captivating 2-hour sunset dinner cruise around the waters of Key West for $89.95 per person.
Indulge in a tropical food buffet, including roast pulled pork, deep-fried plantains, and more, while sipping on an open bar of margaritas, rum runners, and other libations.
Groove to the live music on the upper deck as you take in panoramic views of the sunset over the Gulf of Mexico.
With a 4.3/5 overall rating based on 154 reviews, this cruise offers excellent value and an unforgettable experience.
Remember to bring your passport or ID, as the meeting point is at 201 William St, Key West, FL 33040.
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Key West: Sunset Sailing Trip With Open Bar, Food and Music
Aboard the Sandie Cat, a 149-passenger catamaran, you’ll embark on a captivating 2-hour sunset sailing adventure in the waters of Key West.
As the sun dips below the horizon, you’ll savor an open bar with drinks like rum runners, Champagne, margaritas, and draft beer.
Complementing the libations are appetizers like Swedish meatballs, veggie treats, and meat and cheese platters.
Live music and dancing on the upper deck set the mood as you get the chance to help raise the sails and steer the boat.
With 4.5/5 ratings and free cancellation, this sunset sail is an unforgettable way to experience Key West.
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Key West: Schooner Day Sail With Onboard Bar
Sail aboard the elegant Schooner America 2.0 for a captivating 1.5-hour journey through the waters of Key West.
You’ll sail past iconic sights like Fort Zachary Taylor and Mallory Square, with the chance to spot dolphins, sea turtles, and water birds.
Enjoy complimentary soft drinks and water, and upgrade to 2 alcoholic drinks if you’re 21+.
The 105-foot sailboat features teak decks, mahogany trimmings, and 3,600 square feet of sail.
Depart from the meeting point behind the Schooner Wharf Bar, and bring your passport or ID.
With an overall rating of 4.7/5, this sailing trip offers excellent value and an unforgettable experience.
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Key West: Sunset Snorkel Cruise With Draft Beer & Wine
The allure of Key West’s vibrant sunsets beckons travelers to embark on a captivating 3-hour Sunset Snorkel Cruise.
For $69.95 per person, you’ll snorkel over the world’s third-largest coral barrier reef, with snorkeling gear and safety equipment provided.
After an hour of exploring the ocean’s wonders, you’ll enjoy unlimited cold draft beer and wine as you leisurely sail back, taking in unobstructed views of the sunset over the Gulf of Mexico.
Soft drinks and water are included, and the cruise is suitable for couples, groups, solo travelers, and families.
With a 4.7/5 rating based on 47 reviews, this tour offers excellent value for money.
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Frequently Asked Questions
What Is the Duration of Each Tour?
The duration of each tour typically ranges from 2 to 3 hours, allowing you to explore the vibrant nightlife and sample a variety of local beverages at your own pace. The specific timing may vary depending on the tour itinerary.
Are There Any Age Restrictions for the Tours?
Most drinking tours have age restrictions, typically requiring participants to be at least 21 years old. You’ll want to confirm the age policy before booking your tour to ensure you meet the requirements.
Can I Bring My Own Alcoholic Beverages on the Tours?
Generally, you can’t bring your own alcohol on drinking tours. Most companies provide the drinks as part of the tour experience. It’s best to check with the specific tour operator for their policies on outside beverages.
What Is the Policy on Seasickness or Motion Sickness?
If you experience motion sickness, most tour operators provide seasickness remedies or allow you to disembark early if needed. It’s best to discuss any medical concerns with the tour company before booking to ensure they can accommodate your needs.
Are There Any Dietary Accommodations Available on the Tours?
Many tour companies offer dietary accommodations upon request, such as vegetarian, vegan, or gluten-free options. Be sure to inform the tour operator of any dietary needs when booking your tour to ensure they can accommodate your requirements.
Recap
Key West offers a variety of fun and lively drinking tours to experience the island’s vibrant nightlife. From sunset sails with open bars and live music to pub crawls and snorkeling cruises, there’s something for all to enjoy. Whether you’re looking for a relaxing evening or a night of bar-hopping, these tours provide a great way to make the most of your time in Key West.