Key West stands out as a prime destination for drinking tours thanks to its lively waterfront, historic pubs, and vibrant sunset celebrations. Unlike many Caribbean islands, Key West offers a unique mix of elegant schooner cruises, spooky pub crawls, and intimate private boat charters, all with stunning water views and a relaxed island vibe. Whether you’re into sipping cocktails during a sunset sail, exploring haunted bars, or enjoying a private tiki boat with friends, the options here are surprisingly diverse and full of character.
What makes these tours particularly appealing is their focus on authentic experiences—like tasting local drinks, hearing colorful stories, or simply soaking in the scenery. Plus, with options ranging from budget-friendly pub crawls to luxurious private charters, there’s something for almost every traveler. Ready to explore? Below is a carefully curated list of the top drinking tours in Key West, each with its own style and twist.
1. Key West Schooner Sunset Sail with Bar & Hors d’oeuvres
At number 1, the Key West Schooner Sunset Sail with Bar & Hors d’oeuvres offers an elegant way to unwind as the day ends. This 2-hour cruise aboard a replica of the 1851 Schooner America takes you past key sights like Fort Zachary and Sand Key Lighthouse, giving a water-level perspective you won’t forget.
Your experience includes complimentary hors d’oeuvres and an assortment of beer, wine, and champagne. The crew’s professionalism earns rave reviews, with many mentioning the “exceptional staff” and “beautiful sunset views.” The trip’s blend of scenic sailing and a relaxed bar atmosphere makes it perfect for couples or anyone looking to combine sightseeing with a mellow drink. The main downside? It’s assigned seating, so arriving early helps secure a good spot for sunset.
Bottom line: This cruise is best for those who appreciate a scenic, laid-back experience with quality drinks and tasty snacks, all wrapped in elegant sailing.
2. Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt
Step into Key West’s spooky side with the Haunted Pub Crawl and Ghost Tour. This 2-hour tour combines haunted stories with visits to some of the oldest, most eerie bars in Old Town, including haunted mansions and even a former morgue.
Led by a lively guide, you’ll hear stories of paranormal activity in places like Captain Tony’s and the Porter Mansion, making it both fun and a little creepy. The tour also offers a souvenir T-shirt, which doubles as a reminder of your spooky night. The experience is perfect for those interested in local legends and history, with reviews praising the guide’s humor and storytelling.
Bottom line: If you love ghost stories and a good drink, this tour delivers a memorable mix of history, spirits (both paranormal and alcoholic), and fun.
3. Classic Key West Schooner Sunset Sail with Full Open Bar
For around $109, the Classic Key West Schooner Sunset Sail with Full Open Bar offers an authentic sailing experience paired with a limitless selection of cocktails, wine, and spirits. This 2-hour voyage glides past iconic spots like Mallory Square and Sunset Key, capturing those postcard-perfect moments.
Guests frequently mention the attentive crew, the “beautiful sunset,” and the unlimited drinks that add a celebratory feel to the cruise. It’s an excellent choice for anyone wanting to enjoy the sunset in style, with some reviews noting how the crew actively makes the experience special. The only potential drawback is that some guests felt it lacked historical commentary, focusing more on the scenery and drinks.
Bottom line: Ideal for travelers seeking a relaxing, all-you-can-drink sunset experience with a touch of elegance and stunning scenery.
4. Key West: Sunset Sailing Trip with Open Bar, Food and Music
At number 4, this Sunset Sailing Trip with Open Bar, Food, and Music combines lively entertainment with scenic sailing. It’s a 2-hour journey on a catamaran with a full open bar and a tasty selection of appetizers, plus live music to dance under the stars.
Reviewers rave about the “beautiful cruise,” “great food,” and “fantastic music,” making it perfect for celebrating a special evening or just enjoying a lively night out. The cruise also tends to be well-paced, with friendly staff and a relaxed atmosphere. One consideration is that weather can impact the sunset view, but even without perfect weather, many still report a memorable experience.
Bottom line: Suited for those who want a fun, upbeat evening with drinks, music, and stunning sunset views, ideal for groups or couples seeking a lively atmosphere.
5. Schooner Appledore Day Sail with Full Bar in Key West
For an immersive sailing experience, the Schooner Appledore Day Sail is a standout. This 2-hour cruise on a 2-masted schooner emphasizes hands-on participation — helping raise sails, steering, and enjoying the expansive decks.
The trip includes a full bar and often receives praise for the “peaceful sailing” and “beautiful scenery.” Captain Josh and his crew bring a genuine enthusiasm that enhances the whole adventure. It’s perfect for travelers who want more than just a scenic ride—they want a taste of traditional sailing combined with a laid-back bar experience.
Bottom line: Best suited for those interested in classic sailing with active involvement, excellent scenery, and a friendly crew.
6. Key West: Sunset Dinner Cruise with Open Bar & Live Music
Offering a blend of dinner and drinks, the Sunset Dinner Cruise with Open Bar & Live Music is a 2-hour event on the Gulf of Mexico. Guests enjoy panoramic views, a tropical buffet, and live music on the upper deck, creating a true dinner-and-a-show experience.
Reviewers mention the “delicious food” and “friendly staff,” with many noting it as a romantic way to end a day. The unlimited drinks, including rum punch and tropical cocktails, make it a lively, social experience, though some suggest arriving early to get the best seats. It’s especially good for celebrating anniversaries or special occasions.
Bottom line: Perfect for travelers seeking a relaxed dinner cruise with drinks and live music in a stunning setting.
7. Key West: Afternoon Reef Snorkel Tour with Open Bar
For those who balance water activity with a drink in hand, the Afternoon Reef Snorkel Tour combines a 3-hour snorkeling adventure with an open bar on the boat. You’ll explore the North America’s only living coral barrier reef, spotting fish, sea turtles, and even sharks.
The crew is known for being “great with kids,” and the reef is colorful, making it a family-friendly option. After snorkeling, guests enjoy cocktails, beer, wine, and soda while cruising back. Many reviewers highlight the “friendly, entertaining staff” and “beautiful reef experience.”
Bottom line: A good pick for families or those who want to combine snorkeling with casual drinks in a comfortable, relaxed setting.
8. Key West: 2 Reef Snorkel With Sunset Cruise, Includes Drinks
This tour offers the chance to snorkel at two reefs and then relax with unlimited drinks on the way back, all aboard a modern catamaran. The Sunset Snorkel & Drinks Cruise combines underwater views with a sunset sail.
Guests love the “dolphins swimming alongside” and the “unlimited draft beer and wine.” The reef sites are described as “beautiful and lively,” making it suitable for beginners and experienced snorkelers alike. The cruise tends to be intimate, with fewer reviews, but those who go love the combination of adventure and relaxation.
Bottom line: Great for snorkelers who want a laid-back cruise with endless drinks and the chance to see dolphins.
9. Key West Haunted Pub Crawl Walking Tour
At number 9, the Haunted Pub Crawl Walking Tour mixes history, ghost stories, and pub-hopping. Over about 2 hours, you visit historic pubs like Capt. Tony’s and Shots and Giggles, hearing tales of paranormal activity and murder.
The tour is well-rated for its entertaining guide and interesting stories, making it appealing to those who enjoy a spooky narrative while sampling local drinks. Some reviews indicate that it’s more focused on storytelling than just drinking, which adds a different flavor compared to typical pub crawls.
Bottom line: This tour suits visitors interested in the haunted side of Key West, paired with some good local drinks.
10. 2-Hour Private Sunset Cruise on a Tiki Bar Boat in Key West
For those seeking complete privacy, the Private Sunset Cruise on a Tiki Bar Boat offers an intimate 2-hour experience for up to six people. You bring your own drinks and snacks, and the boat features a Bluetooth stereo, private restroom, and cozy seating.
It’s perfect for celebrating a special occasion or enjoying a quiet evening with friends. The captain points out landmarks like Sunset Pier and Mallory Square, making it a customized, relaxing experience. The reviews highlight the “personable captain” and “beautiful sunset views.”
Bottom line: Best suited for small groups or couples wanting a private, flexible cruise with personalized touches.
11. Key West: 2.5-Hour Duval Street Pub Crawl
If you’re in the mood for a classic pub crawl, the Duval Street Pub Crawl features five pubs with a scheduled cocktail at each stop, plus a souvenir T-shirt. It’s a 2.5-hour journey through the most famous street in Key West, with a lively guide leading the way.
Reviews highlight the fun guide and the chance to meet new people while trying different drinks. It’s a good option for those wanting a social outing and a taste of local bar culture. Some mention that it’s more about the experience than the drinking itself.
Bottom line: Perfect for social travelers looking for a lively, energetic way to experience Duval Street’s bar scene.
12. Private Boat Tour to Sand Bar Snorkel Dolphins and Sunset
This private 3.5-hour tour offers a personal touch, with a local captain taking you to dolphin sightings, snorkeling, and sunset viewing. The boat is your own space, with options like paddleboarding and light tackle fishing.
Reviews praise Vaughn’s “comfortable boat” and “attention to detail,” with many guests saying they extended their trip because of the relaxing environment and wildlife sightings. It’s ideal for those who want an all-in-one water experience with drinks and nature.
Bottom line: Suited for travelers wanting a tailored, intimate water day including snorkeling, dolphin watching, and sunset views.
13. Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat
The 4-hour Private Sandbar Cruise offers exclusive privacy for groups of up to six. You’ll explore the turquoise waters, visit a sandy island, and relax on a floating lily pad.
Guests rave about the captain Patricia’s attentiveness and the “gorgeous” sandbar. The experience emphasizes private, social distancing-friendly fun with plenty of space for your crew to swim, sunbathe, or just chat over drinks brought onboard.
Bottom line: Ideal for groups seeking private, flexible water fun with plenty of time to relax and enjoy the scenery.
14. Key West: Schooner Day Sail with Onboard Bar
This 1.5-hour Schooner Day Sail combines elegance with ease. It’s a shorter trip but offers sights like Fort Zachary, Sunset Pier, and the chance to see dolphins and sea turtles. Plus, it includes a beverage package with two drinks for those over 21.
Guests mention how “beautiful and graceful” the boat is, and the crew’s professionalism. Kids under 12 sail free, making it family-friendly. Its shorter duration makes it perfect for those with limited time or wanting a quick escape.
Bottom line: Best for travelers wanting a brief but beautiful sailing experience with a couple of included drinks.
15. Key West: Bone Island Haunted Pub Crawl
The Bone Island Haunted Pub Crawl explores three haunted pubs over 2 hours, combining history and ghost stories with drinks. Led by the lively guide Gene, you’ll visit legendary spots like Captain Tony’s and learn about paranormal tales tied to the island.
Reviewers enjoy the entertaining storytelling and the mix of spooky legends with pub stops. It suits those interested in a haunted twist on their night out but still want to sample local beers and cocktails.
Bottom line: Ideal for ghost story lovers who want a fun, social way to explore Key West’s haunted watering holes.
16. Key West: Private Tiki Bar Party Boat & Mini Sandbar
Lastly, the Private Tiki Bar Party Boat provides an exclusive 2-hour cruise with your own crew. Featuring a floating tiki bar, the trip includes access to a 6 x 18 floating mat and the chance to swim at a nearby sandbar.
Reviews highlight the “fun time” and “excellent captain,” with plenty of space for relaxing, swimming, and drinking. It’s perfect for those wanting a private, customizable water day with a tropical twist.
Bottom line: Best suited for small groups seeking private, flexible fun with plenty of opportunities to relax, swim, and enjoy drinks.
How to Choose Your Perfect Drinking Tour in Key West
When selecting your ideal experience, consider your budget, time, and what kind of atmosphere you prefer. For romantic sunset moments, the Key West Schooner Sunset Sail with Bar & Hors d’oeuvres or the Full Open Bar Schooner Sail are excellent choices. Looking for a spooky twist? The Haunted Pub Crawl and Bone Island Haunted Pub Crawl blend ghost stories with drinks. For private celebrations, the Private Tiki Bar Boat or the Sandbar Private Cruise offers intimate, customizable options.
Budget-conscious travelers may prefer shorter tours like the Duval Street Pub Crawl or the Sunset Dinner Cruise. Think about your activity level, too — if you want to actively participate, opt for the Schooner Appledore Day Sail.
Booking early is wise, especially for popular sunset cruises and private charters during peak season. Check availability and read recent reviews to ensure your experience matches your expectations.
To sum it up, whether you’re after a romantic sunset cruise, a ghostly pub crawl, or a private water party, Key West offers a rich selection of drinking tours that highlight its water-based charm and lively drinking culture. For a relaxed, scenic experience, the schooner cruises shine. For a touch of the supernatural, the haunted pub tours deliver. And for complete privacy and luxury, the tiki boat options are tough to beat. Explore your options, book early, and get ready for a memorable sip of Key West’s spirited side.