Key West’s drinking tours blend local culture with island hospitality. The best options include sunset sailing cruises – perfect for combining drinks with postcard-worthy views of the Gulf. History buffs will appreciate the Old Town pub crawls, where expert guides share entertaining tales of pirates and haunted spots between stops.
We especially like the sunset sail tours for their mix of nature and comfort, typically featuring quality rum drinks and light snacks. The historic pub crawls earn our recommendation for their rich storytelling and authentic local hangouts, far from the tourist traps.
These top-rated tours await in our detailed guide below.
Good To Know
Key West offers a variety of sunset sails and pub crawls with options for full bars, premium experiences, and haunted themes, accommodating groups of 22 to 80 guests.
Private and specialty tours emphasize relaxation, personalized experiences, and unique features like Tiki Bar Boat Cruises with BYOB and dog-friendly options.
Sunset sails and pub crawls provide a range of food and beverage offerings, including local flavors, craft beer, California wine, and complimentary drinks.
Tours across Key West boast high ratings and exceptional service, with guests praising the atmospheric highlights and unique experiences like engaging guides and themed tours.
Key West also offers adventure and eco-tours, including dolphin watching, snorkeling, and water sports activities, catering to various fitness levels and group sizes.
Key West Sunset Sail With Full Bar, Live Music & Hors Doeuvres
For a memorable evening on the waters of Key West, the Key West Sunset Sail with Full Bar, Live Music, and Hors D’oeuvres offers an unparalleled experience.
Aboard a 70-foot catamaran with over 1,500 feet of deck space, guests can savor a sunset while indulging in a full liquor bar, ice-cold beer, soft drinks, and hearty appetizers.
With a maximum capacity of 80 travelers, the late afternoon sail features live music to enhance the atmosphere.
Travelers rave about the exceptional service, beautiful views, and friendly crew.
However, some suggest improved directions to the meeting point and ensuring groups are booked on the same boat.
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
The Original Key West Pub Crawl takes participants on a lively 2.5-hour exploration of the island’s iconic bar scene.
Led by knowledgeable local guides, the tour visits five popular watering holes, including Duval Street, Rick’s Key West, and Durty Harry’s.
Along the way, guests receive a free souvenir t-shirt and five complimentary drinks, allowing them to experience Key West’s vibrant nightlife.
With a maximum of 35 travelers, the pub crawl offers an intimate and engaging experience, complete with historical insights and ghost stories.
Wheelchair-accessible and pet-friendly, this top-rated tour is a must for anyone seeking an authentic taste of Key West’s legendary bar culture.
Read our full review: Original Key West Pub Crawl Review
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Key West Premium Sunset Sail Aboard Schooner With Full Bar
Travelers seeking a more premium and intimate Key West experience can embark on the Key West Premium Sunset Sail Aboard Schooner With Full Bar.
This highly-rated sunset cruise is recommended by 98% of travelers and has earned a Badge of Excellence. With a maximum of 22 guests, the classic schooner offers a relaxing atmosphere compared to larger, louder cruises.
Guests can enjoy provided hors d’oeuvres and unlimited drinks, including beer, wine, cocktails, and homemade tropical sangria, while passing by Mallory Square and Navy Mole.
Though the $109 per person price is slightly higher than some tours, reviewers emphasize the exceptional service, delicious snacks, and beautiful sunsets that make the experience worthwhile.
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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 an evening of entertainment and relaxation on the water.
This highly-rated 4.5-star cruise provides an open bar, live music, and appetizers as guests sail during sunset. The cruise takes place aboard the newest catamaran in Key West, ensuring a stylish experience.
Guests enjoy unlimited drinks, including well drinks, draft beer, and rum cocktails, as well as Jamaican jerk chicken sliders and other hors d’oeuvres.
The lively atmosphere features live musical performances, with opportunities for dancing. While some guests note room for improvement in food variety and music selection, most recommend the cruise for its friendly crew, stunning views, and memorable experience.
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
Guests can hop aboard the 47-foot catamaran for the Key West Cocktail Cruise, an adults-only sunset experience featuring an open bar.
The 2-hour cruise along the Floridian coast offers unlimited South Florida craft beer, California wine, and hand-crafted cocktails. While food isn’t included, guests can bring their own snacks.
The tour has a maximum capacity of 35 travelers and boasts a 96% recommendation rate from 140 reviews.
Although the cruise is non-refundable, with an additional $10 fuel fee per guest, the experience promises a relaxing atmosphere, live commentary from the captain, and photo opportunities against the backdrop of a beautiful sunset.
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Schooner Key West Day and Sunset Cruises With Full Bar
For those seeking a more traditional sailing experience in Key West, the Schooner Key West Day and Sunset Cruises provide an idyllic option.
Aboard the 49-passenger schooner, travelers can enjoy a 2-hour sail featuring ocean breezes, stunning sunset views, and a full bar offering premium beverages. The cruise departs from the Historic Seaport, with a reputation for friendly, knowledgeable crew.
With a 96% recommendation rate and 5-star reviews, this classic sailing adventure is a must for those looking to relax and take in the beauty of Key West from the water.
The cruise offers cheese platters during sunset sailings and access to onboard restrooms, creating a well-appointed experience.
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Key West Haunted Pub Crawl and Ghost Tour
The Key West Haunted Pub Crawl and Ghost Tour provides an engaging and spooky experience for those seeking to explore the island’s paranormal history.
The 2-hour tour takes visitors through the historic Old Town, visiting haunted mansions and a former morgue while hearing local storytelling. Guests will stop at renowned bars like Captain Tony’s Saloon and Hard Rock Café, known for their ghostly pasts.
The tour includes a souvenir t-shirt and is led by knowledgeable local guides. With a maximum group size of 25, the tour is accessible for wheelchair users and allows strollers and service animals.
Reviews praise the engaging guides and the memorable, spine-tingling atmosphere.
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 the Key West Haunted Pub Crawl Walking Tour takes guests through the historic Old Town, it’s more than just a typical bar-hopping experience.
Led by engaging guides like Chris, Cheryl, and Maggie, the 2-hour tour immerses participants in Key West’s rich history and ghostly legends. Guests will visit renowned haunts like Capt Tony’s Saloon, all while sipping on included alcoholic beverages.
With a maximum of 20 attendees, the tour offers an intimate setting for learning about the island’s paranormal past. While some visitors wished for more access to private buildings, the majority praised the knowledgeable guides and fun atmosphere.
At $29.99 per person, the Key West Haunted Pub Crawl Walking Tour provides a unique and entertaining way to explore the city’s spooky 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
Seeking a unique and relaxing way to explore Key West’s natural wonders? Consider the Private Key West Boat and Sand Bar Adventure.
This 5-star rated tour provides a personalized experience, allowing up to 6 guests to kayak, paddleboard, or simply lounge on a secluded sandbar.
Venture into mangrove forests, tidal creeks, and diverse marine ecosystems, all while a knowledgeable local captain guides you.
Floating rafts and bottled water are provided, and guests can bring their own snacks and drinks.
The tour departs from a convenient location and is dog-friendly.
With moderate physical fitness required, this adventure offers a perfect blend of exploration and relaxation in the Florida Keys.
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2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West
Cruising the waters of Key West aboard a private Tiki Bar Boat offers an unparalleled sunset experience.
Priced at $456.88 per group, this 2-hour cruise is provided by Tiki Boat Adventures, boasting a 90% recommendation rate from 61 reviews. Guests can BYOB and enjoy the included bottled water, ice, and cups.
The boat is equipped with Bluetooth TV and stereo, as well as a restroom. The route passes by iconic Key West landmarks, with the captain offering commentary on the local wildlife and sights.
While some guests expected a more party-like atmosphere, the overall feedback praises the friendly captains and beautiful sunsets. Gratuity of $50+ per couple is suggested based on satisfaction.
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
Embarking on a dolphin watching cruise and snorkeling adventure, travelers in Key West can experience the area’s renowned natural wonders.
Operated by Attractions4us LLC, the tour offers a maximum of 25 participants the chance to spot dolphins off the coast of the Florida Keys and explore nearby reef systems.
With unlimited beer and soft drinks available onboard, the 4.0-rated experience provides scenic views during the cruise.
While weather conditions can occasionally impact snorkeling locations, the knowledgeable and friendly crew consistently manages to deliver an informative and enjoyable outing.
Priced from $89.99 with free cancellation up to 24 hours prior, this tour is a must-do for visitors seeking a unique blend of wildlife, water activities, and refreshments.
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
For those seeking a more intimate and personalized exploration of Key West’s natural wonders, the Key West Sand Bar, Sunset and Eco Trip offers a unique opportunity.
Led by a husband and wife naturalist team, this private tour accommodates groups of up to 6 people, providing a focused and informative experience. Priced at $900 per group, the tour includes the use of snorkeling equipment, bottled water, and transportation in an air-conditioned vehicle.
With a 5.0 rating from 8 reviews, this eco-friendly adventure is accessible to most travelers, allowing them to discover the area’s sandbar and wildlife.
Cancellation is free up to 24 hours in advance, offering flexibility for guests.
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
This full-day tour offers travelers an exciting adventure in Key West, blending wildlife encounters, snorkeling, and sightseeing.
Start the day with a dolphin watching excursion, then explore one of the world’s largest reefs through snorkeling. An open bar is included, and a 1-day Hop-On Hop-Off tour on the Conch Train provides access to local attractions like the Ernest Hemingway Home and Museum and the Key West Lighthouse.
The tour also includes admission to the Sails and Rails Museum for a historical perspective.
With a maximum of 80 travelers, this experience is suitable for most participants, though it’s not wheelchair accessible.
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
Travelers seeking to experience the vibrant marine life and stunning sunsets of Key West can embark on a captivating Dolphin Watching & Snorkeling excursion, followed by a Sunset Dinner Cruise with an open bar.
This 3-hour activity includes snorkeling at one of the only living coral reefs in North America and the chance to see dolphins leaping from the water.
The sunset dinner cruise features an unlimited open bar and live music, along with a delectable Caribbean-inspired menu.
While reviews are mixed, many praise the knowledgeable crew and enjoyable activities.
Participants should plan for the time between events and pack light for the boat.
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
Nestled in the heart of Key West, the “Key West 12 Water Sport Activities Experience Plus Free Beer” offers adventurous travelers a full day of aquatic thrills and unlimited refreshments.
This package includes jet skiing, parasailing, snorkeling, and access to a water park, along with use of snorkeling equipment, a free lunch, and unlimited draft beer.
Ideal for families, the experience starts at 10 am and ends back at the meeting point on William Street.
While not wheelchair accessible, the moderate physical fitness level required ensures an exhilarating day on the water.
Though feedback is mixed, with some issues regarding cancellations, another review praises it as the best activity in the Keys.
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 experience on the water, the Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music presents an evening of stunning vistas and delectable cuisine.
The cruise departs from the Historic Seaport Pier, where guests can check-in 30 minutes prior to embark on a 56-passenger tour. The dinner buffet offers vegetarian options, while the open bar serves tropical-inspired drinks.
Guests can enjoy live music as they witness the spectacular Key West sunset. Though not wheelchair accessible, the cruise is suitable for most travelers, including those looking for a romantic retreat or corporate affair.
With an overall rating of 2.5 out of 5 stars, this cruise may not be the top choice, but it still offers a unique way to experience the beauty of Key West.
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
Encompassing both the tranquil allure of a sunset sail and the underwater exploration of a morning snorkeling adventure, this multifaceted Key West experience offers a well-rounded glimpse into the island’s natural wonders.
The sunset dinner cruise includes an open bar, tropical buffet, and live music, while the morning snorkeling trip features fresh juices, muffins, fruit, and cereals.
Operated by Attractions4us LLC with a maximum of 80 travelers, both activities depart from the convenient meeting point in downtown Key West.
With flexible booking and cancellation policies, as well as accessibility near public transportation, this tour caters to most travelers seeking an immersive day of sightseeing and relaxation in the Florida Keys.
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
This full-day combo tour from Miami to Key West provides travelers with an opportunity to experience the best of the Florida Keys.
The tour includes beach time at Smathers Beach and a sunset sail on a catamaran with an open bar and live music. During the day, guests can enjoy unlimited water activities like snorkeling, kayaking, and paddleboarding.
The sunset sail experience features an open bar with unlimited well drinks, enhancing the relaxing cruise.
Transportation is provided from Miami, and the tour accommodates up to 90 travelers.
With free cancellation up to 24 hours before the experience, this tour offers a flexible and enjoyable way to explore Key West.
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 range of drinking tours for visitors. From sunset sails with open bars and live music to pub crawls and cocktail cruises, there’s something to suit every taste. These tours provide a fun and immersive way to experience the island’s vibrant nightlife and stunning natural scenery. Whether you’re looking for a relaxed evening or a lively night out, Key West has the perfect drinking tour for you.