Practical drinking tours dominate Key West’s entertainment scene, offering excellent value and local insights.
Sunset sailing excursions stand out, combining waterfront views with open bars on spacious catamarans – perfect for groups and celebrations.
The guided pub crawls prove consistently reliable, hitting the essential Duval Street spots while sharing island history.
Particularly worthwhile is the Ghost & Gravestones tour, which mixes haunted tavern visits with fascinating old town stories.
These tours range from $40-80 per person, typically including drinks and extras like souvenir t-shirts or drink vouchers.
Evening sailing tours run 2-3 hours, while walking pub crawls last about 3 hours.
Let’s examine our favorite Key West drinking tours ranked by quality and value.
Key Points
- The Key West Pub Crawl offers a 2.5-hour guided tour of five popular bars, including sampling local cocktails and a free souvenir t-shirt.
- The Haunted Pub Crawl and Ghost Tour provides a spooky 2-hour experience exploring haunted bars and mansions with a knowledgeable local guide.
- The Key West Sunset Sip and Sail combines sunset views, live music, and an open bar with appetizers for an energetic drinking experience.
- The Key West Sunset Dinner Cruise offers a 2-hour cruise with an open bar, live music, and a tropical food buffet.
- The Dolphin Watching Cruise during the Snorkeling Adventures tour provides unlimited beer and soda while exploring the world’s third-largest coral barrier reef.
Key West Sunset Sail With Full Bar, Live Music and Hors Doeuvres
A stunning 60-foot catamaran sets sail from Key West, offering a captivating sunset experience.
Aboard this 1,500-foot deck space, you’ll enjoy an all-inclusive full liquor bar and a chef’s selection of hors d’oeuvres, including shrimp cocktail. Local Key West musicians provide live entertainment throughout the cruise, creating a lively atmosphere.
During the 60-minute sail, you’ll take in views of the Key West seaport, Mallory Square, the Navy Mole, and Fort Zachary Taylor Historic State Park.
With a maximum capacity of 80 travelers, this sunset sail offers an intimate and memorable experience. Just be sure to arrive 30 minutes early for a smooth check-in process, as this tour is likely to sell out.
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
Embark on an intimate and unforgettable Classic Key West Schooner Sunset Sail with a full open bar.
Recommended by 98% of travelers, this tour offers a 5.0-rated experience with a maximum of 22 guests.
Enjoy unlimited beer, wine, champagne, and soft drinks as you sail along the scenic Key West coast.
The friendly and attentive crew will provide engaging stories and the opportunity to captain the vessel.
Savor delectable appetizers and relish the peaceful atmosphere, away from the typical party cruise.
With a Badge of Excellence and positive customer reviews, this relaxing sunset sail is a must-try for those seeking a unique drinking experience in Key West.
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Sunset Sip and Sail Key West With Open Bar and Live Music
Although the Classic Key West Schooner Sunset Sail offers a tranquil and intimate experience, the Sunset Sip and Sail Key West with Open Bar and Live Music provides a lively and memorable alternative for those seeking a more energetic sailing adventure.
With an open bar, delectable appetizers, and live music from Key West’s best performers, this cruise combines the best of sunset views and nightlife. The newest catamaran, The Sandie Cat, transports you to stunning vistas while you dance the evening away.
With convenient logistics and a price starting at $79.95 per person, this tour is an excellent choice for those looking to experience Key West’s vibrant culture and entertainment.
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Key West Schooner Sunset Sail With Bar & Hors Doeuvres
Frequently, travelers seek out the serene and intimate Key West Schooner Sunset Sail with Bar & Hors d’oeuvres, a 2-hour excursion aboard the America 2.0.
With a 96% recommendation rate from 559 reviews, this tour offers a Badge of Excellence experience for up to 68 guests.
Complimentary beer, wine, champagne, and soda are served alongside individually plated hors d’oeuvres, and gratuities are included.
While not wheelchair accessible, the tour is stroller-friendly and near public transportation.
Guests should dress for cooler temperatures on the water and be 21+ to consume alcohol.
Holiday-themed sails feature special treats and a champagne toast.
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Original Key West Pub Crawl: the Best Bars With Free T-Shirt
The Original Key West Pub Crawl offers a guided, 2.5-hour tour through the vibrant bar scene of this iconic Florida destination.
You’ll visit five popular establishments, including downtown, the historic seaport, and Duval Street, enjoying a domestic beer or mixed drink at each location.
The tour includes a free souvenir t-shirt and is open to those 21 and older.
Wheelchair accessible, it’s not recommended for pregnant travelers or those with serious health issues.
With a 4.5-star average rating from over 300 reviews, this lively tour promises fun, new friends, live music, and local history and ghost stories, all while sampling specialty drinks like frozen piña coladas.
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Key West Sunset Snorkel With Unlimited Draft Beer & Wine
Combine a sunset sail and snorkeling adventure on the Key West Sunset Snorkel with Unlimited Draft Beer & Wine tour.
Cruise the Atlantic Ocean as you enjoy relaxing music, beverages, and socializing. Snorkel over a vibrant coral reef and spot marine life.
With 110 reviews and a Badge of Excellence, this tour offers excellent value. Inclusions like snorkeling equipment and unlimited alcoholic drinks make for a carefree experience.
Note that the tour isn’t wheelchair accessible, and children must be accompanied by an adult. While most travelers can participate, there have been some complaints about warm beer and check-in confusion.
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Key West Haunted Pub Crawl and Ghost Tour With Free T-Shirt
Set out on a haunting adventure through Key West’s eerie past on the Key West Haunted Pub Crawl and Ghost Tour. This 2-hour experience takes you to bars within haunted mansions and a former morgue, where you’ll hear spooky tales and learn about the island’s dark history.
With a knowledgeable local guide, you’ll visit iconic spots like Hard Rock Café and Captain Tony’s Saloon. The tour accommodates up to 25 travelers aged 21 and over, and a souvenir T-shirt is included.
While food and drinks are available at your own expense, the unique blend of history and fun makes this a must-do activity for those seeking a thrilling night out in Key West.
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Dinghy Drinking Tour Through Key West Waters
Want to explore Key West’s vibrant waterfront bar scene from a unique perspective? The Dinghy Drinking Tour combines coastal scenery and lively bars.
You’ll cruise through mangrove tunnels to two or three waterfront bars on a small motor boat. With a maximum of 10 travelers, this small-group tour offers a personal experience.
Bring your swimwear for possible swimming opportunities. The tour includes a licensed boat captain, coolers, and the freedom to bring your own drinks.
While most travelers rave about the beautiful views and wildlife encounters, some note logistical challenges and limited drink options at certain bars.
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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 lively way to experience the city’s vibrant waterfront.
With over 105 reviews and a 96% recommendation rate, this tour has earned a Badge of Excellence. You’ll depart from the Garrison Bight Marina, arriving 15 minutes early for a seamless start.
The cruise includes ice, cups, bottled water, and a restroom onboard, plus you’re welcome to BYOB and snacks.
While not recommended for those with back problems, the positive guest experiences praise the friendly, knowledgeable captains who create memorable activities like swimming and wildlife sightings.
With free cancellation and a Lowest Price Guarantee, this tour is a must for your Key West drinking adventures.
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)
For those seeking a more intimate and relaxed way to take in Key West’s stunning sunsets, the Key West Tiki Bar Sunset Cruise (By the Seat) offers an unparalleled experience.
With a maximum of 6 travelers, this USCG-certified boat tour promises a personalized adventure. Guests can enjoy ice, cups, and bottled water, while bringing their own alcoholic beverages and snacks.
The knowledgeable and friendly captains provide an informative narrative, creating a relaxed atmosphere. Reviewers highlight the captains’ ability to find unique swimming spots and provide attentive, individualized attention.
At $80.58 per person with a 2-person minimum, this sunset cruise is an excellent choice for those wanting a small-group experience to remember.
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Key West Cocktail Cruise Adults Only Sunset Cruise With Open Bar
Looking to elevate your Key West sunset experience? The Key West Cocktail Cruise Adults Only Sunset Cruise With Open Bar offers an adults-only escape with an open bar, wine tasting, and live commentary from professional guides.
Depart from Garrison Bight Marina, where you’ll board a non-smoking vessel with a maximum of 35 travelers for a more personalized cruise. Enjoy stunning sunset views, friendly crew, and top-notch drinks – all while capturing the moment with your camera.
Just note the $10 per guest fuel and fees, and that no food is included, though you’re welcome to bring your own snacks. With 96% of travelers recommending this cruise, it’s a sunset soirée you won’t soon forget.
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Key West Afternoon Reef Snorkeling With Open Bar
Explore the vibrant underwater world of the Key West Afternoon Reef Snorkeling with Open Bar experience. This 4.5-star tour takes you to the world’s 3rd largest living coral reef, where you’ll discover an abundance of marine life.
Equipped with provided snorkeling gear, you’ll receive expert guidance to make the most of your time in the water. After your snorkeling adventure, indulge in an open bar featuring draft beer, rum runners, margaritas, and more.
With a maximum capacity of 70 travelers, this tour aboard the newest snorkel boat in Key West promises an unforgettable and refreshing afternoon on the water.
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Key West Haunted Pub Crawl Walking Tour
On this captivating Key West Haunted Pub Crawl Walking Tour, you’ll learn about the city’s spooky past as you visit historic haunted pubs and taverns.
Led by an engaging guide, you’ll learn eerie tales and the haunted reputation of each location, including Wine-O Bar and Lounge, Capt. Tony’s Saloon, and Shots and Giggles.
Along the way, you can enjoy alcoholic beverages as you explore these haunted hotspots.
With a maximum group size of 20 travelers, this 2-hour tour provides an intimate and spooky experience.
While not wheelchair accessible or recommended for pregnant travelers, the tour offers free cancellation up to 24 hours in advance, making it a flexible option for your Key West adventure.
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Key West Sand Bar, Sunset and Eco Trip
This private excursion takes you on a memorable journey through the stunning waters surrounding Key West.
You’ll use snorkeling equipment to explore the vibrant marine life, which may include dolphins, sharks, spotted eagle rays, tarpon, and even a loggerhead turtle.
After snorkeling, you’ll spend time sunning and shelling on a scenic sand bar.
The tour also includes a tranquil cruise through a mangrove forest, providing a unique eco-adventure.
With a maximum of 6 guests, this intimate experience offers a personalized and flexible itinerary.
The air-conditioned transportation and complimentary bottled water ensure your comfort throughout the day.
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
Set out on a captivating 2-hour private sunset cruise aboard a tiki-themed boat in the heart of Key West. This highly-rated experience features a Bluetooth TV and stereo for music, allowing you to set the mood for your private party.
Arrive 15 minutes early at the Garrison Bight Marina, where you’ll be met by a USCG-certified captain who’ll guide you on your journey. Cruise past iconic landmarks like Sunset Pier and the Key West Historic Seaport, and keep an eye out for local wildlife.
Although you’re encouraged to BYOB and snacks, bottled water and ice are provided. Expect a relaxed atmosphere without public interaction, though some guests wished for more narration from the captain.
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Key West: Dolphin Watching Cruise & Snorkeling Unlimited Beer & Soda
Enjoy the captivating waters of Key West on this dolphin watching and snorkeling adventure.
Led by a knowledgeable and friendly crew, you’ll have the chance to witness mother and baby dolphins as well as dolphin pods.
Despite potential weather challenges, the crew works hard to enhance your experience, ensuring you make the most of the snorkeling opportunities.
Enjoy unlimited beer and soda as you explore the marine life, with the tour returning to the starting point at the end.
While weather may limit underwater visibility, reviewers highlight the crew’s expertise and the overall must-do nature of this tour for dolphin enthusiasts.
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Key West: Private Tiki Bar Party Boat & Mini Sandbar
Escape the ordinary and indulge in a private tiki bar party boat adventure in the heart of Key West.
Experience a 2-hour cruise with up to 6 people, complete with a floating mat for swimming. Bring your own food and drinks to create a fun, laidback atmosphere.
The price starts from Kč9,683 per group, and you can reserve now and pay later with free cancellation up to 24 hours in advance.
Relax as the US Coast Guard-approved captain navigates the tiki boat, equipped with a cooler, ice, bottled water, and a Bluetooth stereo for music.
Don’t miss out on this unique way to explore Key West’s waterways.
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Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat
For the ultimate Key West experience, hop aboard a private tiki bar boat and set sail on a 4-hour sandbar cruise.
Priced at Kč13,557 for up to 6 people, this private excursion lets you explore the turquoise waters of the Florida Keys in style.
Relax on the floating mat, play with foam noodles, and enjoy your own music through the Bluetooth stereo.
Keep an eye out for wildlife like rays, turtles, and dolphins.
You’ll have a US Coast Guard licensed captain, bottled water, and a full restroom on board.
With free cancellation up to 24 hours in advance, this tour offers excellent value and a memorable experience.
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Key West: Multiple Water Sports Excursion With Lunch & Beer
On this exciting 6-hour excursion, you’ll have the opportunity to try a variety of thrilling water sports in the beautiful waters of Key West.
For $178.95, you’ll enjoy parasailing, jet skiing, snorkeling, and more. Climb aboard the 65-foot Party Cat catamaran and receive instructions from the experienced crew.
After working up an appetite, enjoy a grilled lunch buffet and free draft beer on the return cruise.
With an overall rating of 4.2/5 based on 23 reviews, this excursion is sure to provide an unforgettable day of fun and adventure.
Don’t forget to bring your passport or ID, and be prepared to get wet!
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Miami: Key West Boat Tour W/ Optional Snorkeling & Open Bar
Although you can easily explore Key West on your own, this Miami: Key West Boat Tour with Optional Snorkeling & Open Bar offers a convenient and exciting way to experience the Florida Keys.
Priced from $22.11 per person, the tour includes round-trip transportation, a 3-hour snorkeling, sailing, and sightseeing excursion, and an open bar option.
You’ll have the chance to see marine life like barracudas, sea turtles, and vibrant coral reefs.
While the bus conditions and guide service have received mixed reviews, the overall transportation and value for money ratings are positive.
With free cancellation and no upfront payment required, this tour provides a hassle-free way to make the most of your time in Key West.
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
Embark on an unforgettable excursion with the Key West Tour and Coral Reef Snorkeling With Open Bar.
This 14-hour tour whisks you from Miami to the Florida Keys, where you’ll explore Key West at your own pace for 6 hours. Highlights include visiting landmarks, museums, and local eateries.
Then, board a catamaran for a snorkeling adventure at the Key West Coral Reef, complete with gear, instructors, and refreshing showers. Enjoy unlimited drinks on the catamaran, with alcohol served after swimming.
Round-trip transportation and a live guide in English and Spanish are included. Whether you’re a solo traveler or part of a group, this tour offers an excellent value starting at $2,378 per person.
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Key West: Sunset Dinner Cruise With Open Bar & Live Music
Experience the beauty of Key West’s stunning sunset from the water on the Key West: Sunset Dinner Cruise With Open Bar & Live Music.
This 2-hour cruise features an open bar, live music, and a tropical food buffet. Enjoy panoramic views of the Gulf of Mexico as you dine on roast pulled pork, fried fish, and other island-inspired dishes.
With an overall rating of 4.3/5 from 154 reviews, this cruise offers great value for money. Transportation is included, and you can cancel up to 24 hours in advance for a full refund.
Don’t forget to bring your passport or ID card, as gratuities aren’t included in the price of €85.41 per person.
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Key West: Sunset Sailing Trip With Open Bar, Food and Music
For a stunning sunset sailing adventure in Key West, the Key West: Sunset Sailing Trip With Open Bar, Food and Music is a must-try.
You’ll sail on the Sandie Cat catamaran, which can accommodate up to 149 passengers across 3 decks, offering unobstructed sunset views.
Enjoy an unlimited open bar with drinks like rum runners, Champagne, margaritas, and draft beer, along with a selection of appetizers.
The 2-hour trip also features live music and dancing on the upper deck.
With an overall rating of 4.5/5 from 210 reviews, this experience is likely to sell out, so book now for $69.95 per person with free cancellation up to 24 hours in advance.
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Key West: Schooner Day Sail With Onboard Bar
If a serene sailing adventure is more your pace, the Key West: Schooner Day Sail With Onboard Bar offers a tranquil excursion on the waters of the Florida Keys.
For $1,756 per person, you’ll embark on a 1.5-hour journey aboard the 105-foot sailboat, Schooner America 2.0. Admire the elegant teak decks and mahogany trimmings as you sail past Fort Zachary Taylor, Sand Key reef, Mallory Square, and Sunset Pier.
Keep an eye out for dolphins, sea turtles, and water birds. Complimentary soft drinks and water are included, and you can bring your own picnic lunch. Those 21 and older can enjoy an optional drink upgrade.
With an overall rating of 4.7/5, this sailing trip promises excellent crew, friendly service, and a knowledgeable captain.
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Key West: Sunset Snorkel Cruise With Draft Beer & Wine
Set out on a captivating 3-hour sunset snorkel cruise in Key West, where you’ll have the opportunity to explore the world’s third-largest coral barrier reef.
Enjoy unlimited cold draft beer and wine after snorkeling as you sail across sparkling waters and take in the unobstructed view of the sunset over the Gulf of Mexico.
The cruise includes snorkeling gear, soft drinks, water, hotel pickup and drop-off, and gratuities.
With an overall rating of 4.7/5 from 47 reviews, this tour offers excellent value for money.
The friendly crew, beautiful scenery, and enjoyable snorkeling experiences make this a must-do activity for your Key West visit.
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The Sum Up
Explore Key West’s vibrant nightlife on a range of exciting drinking tours. From sunset sails with open bars and live music to pub crawls and dinner cruises, there’s something to suit every taste. Savor the local flavors, take in stunning views, and make unforgettable memories on these immersive experiences. Whether you’re a first-time visitor or a seasoned local, these tours offer an unbeatable way to discover the best of Key West’s vibrant drinking scene.