Practical and well-organized drinking tours make Key West’s bar scene manageable for visitors. The city’s best options include sunset sailing tours – I especially love the intimate schooner cruises where you can enjoy cocktails without the party-boat atmosphere. The sunset sails with appetizers and live music offer excellent value, combining drinks with entertainment and stunning views. For active travelers, several companies pair water activities with included beer – a refreshing combination that works surprisingly well.
My personal favorite remains the dinner cruise option, which provides a full meal along with unlimited drinks in a more sophisticated setting. These tours range from 12 to 100 passengers, making them suitable for couples or larger gatherings.
Let’s explore Key West’s most worthwhile drinking tours.
Good To Know
- The Premium Sunset Experiences offer an adults-only cocktail cruise with unlimited craft beer, wine, and cocktails on a classic schooner.
- The Key West Sunset Buffet Dinner Cruise provides a buffet dinner and open bar for 56 guests, featuring live music.
- The Key West 12 Water Sport Activities package includes jet skiing, parasailing, and snorkeling with unlimited draft beer and lunch.
- The Smathers Beach & Sunset Catamaran tour combines beach relaxation, sunset sailing, and an open bar with live music.
- Many tours in Key West offer complimentary drinks and appetizers, enhancing the overall drinking and dining experience.
Key West Sunset Sail With Full Bar, Live Music & Hors Doeuvres
Embarking on a sunset sail through the picturesque waters of Key West, travelers can indulge in a captivating experience aboard a 70-foot catamaran.
With a maximum capacity of 80 guests, the Key West Sunset Sail offers an array of amenities, including a full liquor bar, ice-cold beer, soft drinks, and hearty appetizers.
Complemented by live music, the sunset viewing promises to be a highlight, as the boat’s 1,500 square feet of deck space provides ample room to relax and soak in the stunning views.
With exceptional service, positive reviews, and a lowest price guarantee, this tour is an excellent choice for those seeking a memorable evening on the water in Key West.
Read our full review: Key West Sunset Sail With Full Bar, Live Music & Hors Doeuvres Review
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Original Key West Pub Crawl
For travelers seeking to enjoy Key West’s vibrant bar scene, the Original Key West Pub Crawl provides a guided journey through the island’s historic and lively watering holes.
This 2.5-hour tour takes guests to five popular bars, including Duval Street, Rick’s Key West, and Durty Harry’s, offering five complimentary drinks along the way.
Led by knowledgeable local guides, the crawl showcases Key West’s rich history and unique culture, with personable hosts regaling travelers with ghost stories and bar trivia.
Praised for its casual atmosphere and engaging experiences, the Original Key West Pub Crawl is a must for adults looking to explore the city’s legendary nightlife.
Read our full review: Original Key West Pub Crawl Review
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Key West Premium Sunset Sail Aboard Schooner With Full Bar
As the sun dips below the horizon, travelers can enjoy a premium sunset sail aboard a classic schooner in Key West.
This highly-rated experience accommodates a maximum of 22 guests, providing an intimate and relaxing outing. Passengers can help hoist the sails or simply enjoy the views, complemented by hors d’oeuvres and unlimited drinks, including beer, wine, cocktails, and homemade tropical sangria.
The crew’s exceptional service and engaging personalities contribute to the overall enjoyment of this 5-star rated tour. At $109 per person, the Key West Premium Sunset Sail offers a quality experience, though some reviewers note the price as slightly high.
The small group size and beautiful setting make this sunset cruise a popular choice.
Read our full review: Key West Premium Sunset Sail Aboard Schooner With Full Bar Review
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Sunset Sip and Sail With Open Bar, Live Music, and Appetizers From Key West
Sunset Sip and Sail With Open Bar, Live Music, and Appetizers From Key West offers a memorable sunset cruise experience.
Aboard the Sandie Cat, the newest catamaran in Key West, guests can enjoy unlimited well drinks, draft beer, margaritas, rum runners, wine, and champagne, along with a selection of appetizers.
The lively atmosphere is enhanced by live music performances, though some guests noted the music could be better suited for dancing.
With a capacity of 75 travelers, the cruise is praised for its excellent service, stunning views, and the opportunity to make memorable experiences, especially for couples and groups.
Cancellation is available up to 24 hours before the start, priced at $79.95 per person.
Read our full review: Sunset Sip and Sail With Open Bar, Live Music, and Appetizers From Key West Review
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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 aboard a 47-foot catamaran. This 2-hour cruise along the Floridian coast allows up to 35 travelers to indulge in unlimited South Florida craft beer, California wine, and hand-crafted cocktails.
The captain provides live commentary, and guests can capture breathtaking photos of the sunset. While food isn’t included, travelers can bring their own snacks.
The cruise departs from Slip #7 at Garrison Bight Marina, with free parking available. Guests praise the crew’s knowledge and friendliness, as well as the relaxing atmosphere.
However, some have reported issues with communication regarding cancellations due to weather and unexpected fees. The cruise is non-refundable, and a $10 fuel fee per guest is payable to the operator.
Read our full review: Key West Cocktail Cruise Adults Only Sunset Cruise With Open Bar Review
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Schooner Key West Day and Sunset Cruises With Full Bar
Schooner Key West offers travelers a choice between day and sunset cruises aboard their 49-passenger schooner, allowing them to experience the stunning Floridian coastline and ocean views.
The 2-hour sails depart from Key West’s Historic Seaport and feature a premium selection of beer, wine, cocktails, and soft drinks. During the sunset sail, guests can enjoy a cheese platter as they take in the breathtaking display.
This highly-rated tour is recommended by 96% of travelers and has earned a Badge of Excellence from Sebago Key West. The friendly, knowledgeable crew provides a unique sailing experience reminiscent of traditional methods, making this an ideal way to explore Key West from the water.
Read our full review: Schooner Key West Day and Sunset Cruises With Full Bar Review
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Key West Haunted Pub Crawl and Ghost Tour
Set out on a spooky exploration of Key West’s haunted history with the Key West Haunted Pub Crawl and Ghost Tour.
Over the course of 2 hours, you’ll visit historic sites, bars with a haunted past, and learn about the island’s former name, Cayo Hueso.
Led by a knowledgeable local storyteller, the tour takes you through Old Town Key West, with a maximum group size of 25.
You’ll receive a souvenir t-shirt and have the opportunity to visit haunted spots like Hard Rock Café, Captain Tony’s Saloon, and Tattoos & Scars Saloon.
The tour is wheelchair accessible, and guests over 21 with valid photo ID can join.
Read our full review: Key West Haunted Pub Crawl and Ghost Tour Review
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Key West Haunted Pub Crawl Walking Tour
Although Key West is known for its lively nightlife, the city also boasts a haunting past that comes alive during the Key West Haunted Pub Crawl Walking Tour.
This 2-hour walking tour takes guests on a spooky journey through the historic district, where they’ll learn about the island’s ghostly legends and sip on alcoholic beverages.
Led by engaging guides like Chris, Cheryl, and Maggie, the tour has received excellent reviews for its storytelling and ability to immerse guests in the town’s eerie past.
While some visitors noted disappointment with the tour’s length and lack of entry into homes or bars, the majority praised the experience as a fun and informative way to explore Key West’s haunted side.
Read our full review: Key West Haunted Pub Crawl Walking Tour Review
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Private Key West Boat and Sand Bar Adventure
The Private Key West Boat and Sand Bar Adventure offers guests a unique opportunity to explore the diverse marine ecosystems of the region.
With a 97% traveler recommendation and a Badge of Excellence, this private tour takes visitors on a journey through mangrove forests, tidal creeks, and sandbars.
Guests can choose from kayaking, stand-up paddleboarding, or simply relaxing on the floating rafts. The knowledgeable and friendly captain provides guidance, and guests can bring their own snacks and drinks.
The tour is dog-friendly, and a moderate fitness level is required. With morning and afternoon departures available, this adventure is a must-do for nature enthusiasts visiting Key West.
Read our full review: Private Key West Boat and Sand Bar Adventure Review
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2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West
This 2-hour private sunset cruise on a tiki bar boat offers guests a unique and relaxing experience in the waters around Key West.
Operated by Tiki Boat Adventures, the cruise allows up to 6 people to enjoy the beautiful sunset while passing by local landmarks and wildlife. The USCG-certified captain provides informative commentary throughout the journey.
Guests can bring their own alcoholic beverages and snacks, and the boat is equipped with amenities like a Bluetooth TV and stereo, and a restroom.
While most guests praised the friendly captains and serene atmosphere, some expected a more lively party vibe.
Read our full review: 2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West Review
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Key West: Dolphin Watching Cruise & Snorkeling Unlimited Beer & Soda
Operated by Attractions4us LLC, the Key West: Dolphin Watching Cruise & Snorkeling Unlimited Beer & Soda offers guests an exhilarating adventure on the waters surrounding the Florida Keys.
Priced from $89.99, the tour accommodates a maximum of 25 travelers and features dolphin watching, snorkeling at reef systems, and unlimited beer and soft drinks.
With an overall rating of 4.0 from 11 reviews, the tour receives positive feedback on the crew’s friendliness, knowledge, and ability to provide enjoyable experiences despite weather challenges.
The tour departs from and returns to the meeting point at 201 William St, Key West, FL, with free cancellation available up to 24 hours prior.
Read our full review: Key West: Dolphin Watching Cruise & Snorkeling Unlimited Beer & Soda Review
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Key West Sand Bar, Sunset and Eco Trip
Husband and wife naturalist team offer an intimate Key West sandbar/eco trip, providing guests with a private and exclusive experience.
The tour accommodates groups of up to 6 people and is priced at $900 per group. Included in the tour are snorkeling equipment, bottled water, and an air-conditioned vehicle for transportation.
The tour starts and ends at the dock in front of Thai Island restaurant, and it’s accessible to most travelers, though not wheelchair-friendly.
Guests can enjoy free cancellation up to 24 hours before the tour and have the option to reserve and pay later.
With 8 reviews and a 5.0 rating, this tour promises an immersive and educational experience exploring Key West’s sandbar and eco-system.
Read our full review: Key West Sand Bar, Sunset and Eco Trip Review
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Dolphin Morning Watching & Snorkeling Open Bar 1 Day Hop-On Hop-Off Fun
Travelers embark on a captivating adventure with the Dolphin Morning Watching & Snorkeling Open Bar 1 Day Hop-On Hop-Off Fun tour in Key West.
This comprehensive package offers a chance to witness dolphins up close, either from the boat or by snorkeling one of the world’s largest reefs. The tour also includes an open bar, a 1-day pass for the Conch Train, and admission to the Sails and Rails Museum.
With a maximum of 80 travelers and starting at $149.99 per person, the tour provides a unique opportunity to explore Key West’s top attractions, including the Ernest Hemingway Home and Museum and the Key West Lighthouse.
Free cancellation up to 24 hours before the experience ensures flexibility.
Read our full review: Dolphin Morning Watching & Snorkeling Open Bar 1 Day Hop-On Hop-Off Fun Review
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Dolphin Watching & Snorkeling in Key West With Sunset Dinner Cruise and Open Bar
Embarking on a captivating journey, travelers in Key West can indulge in the Dolphin Watching & Snorkeling with Sunset Dinner Cruise and Open Bar experience.
This 3-hour excursion offers the chance to snorkel at a living coral reef and witness dolphins leaping from the water. Following the activities, guests can enjoy a sunset dinner cruise with an unlimited open bar and live music.
The menu features Caribbean-inspired dishes like pulled pork, grilled chicken, and fried fish. With a capacity of 80 travelers, this experience provides a personalized touch.
While customer reviews are mixed, the opportunity to combine dolphin watching, snorkeling, and an evening cruise makes this an enticing option for visitors to Key West.
Read our full review: Dolphin Watching & Snorkeling in Key West With Sunset Dinner Cruise and Open Bar Review
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Key West 12 Water Sport Activities Experience Plus Free Beer
Vacationers seeking a thrilling aquatic adventure can enjoy the Key West 12 Water Sport Activities Experience Plus Free Beer.
This full-day package offers a dozen water-based activities, including jet skiing, parasailing, and snorkeling. Guests can also enjoy unlimited draft beer and a complimentary lunch.
The experience is ideal for families looking to maximize their time on the water, though it requires a moderate level of physical fitness as it’s not wheelchair accessible.
While reviews are mixed, one traveler praised it as the best activity in the Keys, highlighting the excitement of jet skiing and parasailing.
Priced at $299.99 with free cancellation up to 24 hours in advance, this experience provides flexibility and value.
Read our full review: Key West 12 Water Sport Activities Experience Plus Free Beer Review
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Key West Sunset Buffet Dinner Cruise With Open Bar and Live Music
For those seeking a more relaxed and romantic evening on the water, the Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music provides a captivating experience.
Travelers can witness the stunning Key West sunset while enjoying a dinner buffet and tropical-inspired drinks from the open bar. The cruise accommodates up to 56 guests and may be suitable for romantic retreats or corporate affairs.
However, the activity isn’t wheelchair accessible.
With an overall rating of 2.5 out of 5 stars based on 2 reviews, the cruise offers a mixed experience, according to past participants.
Read our full review: Key West Sunset Buffet Dinner Cruise With Open Bar and Live Music Review
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Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling
Travelers visiting Key West can embark on a captivating sunset sail that offers a full bar, live music, and a delectable dinner buffet, followed by an early morning snorkeling adventure.
The sunset cruise lasts 2 hours and is operated by Attractions4us LLC, which can accommodate up to 80 travelers. The morning snorkeling trip runs for 3 hours and includes refreshments like fresh juices, muffins, fruit, and cereals.
Both experiences depart from and return to the meeting point at 201 William St, Key West, FL 33040. Prices start at $159.99 per person, with free cancellation up to 24 hours prior and the option to reserve now and pay later.
While the tours aren’t wheelchair accessible, most travelers can participate.
Read our full review: Key West: Sunset Sail Full Bar, Live Music & Dinner & Early Morning Snorkeling Review
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Key West: Smathers Beach & Activities With a Sunset Catamaran & Open Bar
Visitors to Key West can embark on a full-day adventure that combines relaxation at Smathers Beach with an unforgettable sunset sail on a catamaran.
The tour includes unlimited water activities, such as snorkeling, kayaking, and paddleboarding. During the sunset sail, guests can enjoy an open bar with unlimited well drinks and live music.
Roundtrip transportation from Miami to Key West is provided, and the meeting point is Smathers Beach. The tour can accommodate up to 90 travelers, and it’s stroller accessible but not wheelchair accessible.
Priced from $229.99 per person, the tour offers free cancellation up to 24 hours before the experience.
Read our full review: Key West: Smathers Beach & Activities With a Sunset Catamaran & Open Bar Review
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The Sum Up
Key West offers a variety of lively drinking tours, from sunset sails with open bars and live music to pub crawls and cocktail cruises. Whether you’re looking for a relaxing evening or a wild night out, there’s an excursion to suit your taste. With so many options, visitors can easily find the perfect way to enjoy Key West’s vibrant nightlife.