Key West is a lively place, and its small size makes it perfect for exploring what makes its drinking scene so special. Whether it’s sipping cocktails during a sunset sail or hopping from bar to bar along Duval Street, there’s a tour for every taste. We love how many options combine stunning scenery with a chance to enjoy local libations — like the Key West Schooner Sunset Sail with Bar & Hors d’oeuvres or the Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar. These provide not just drinks, but a memorable experience with great views.
Key West’s charm lies in its small, approachable size and its warm, welcoming drinking spots. The tours here range from relaxed sunset sails to lively pub crawls, perfect for different moods and budgets. Some tours, like the Dinghy Drinking Tour, offer an intimate way to explore waterfront bars, while others, such as the Sunset Sip and Sail, combine music, drinks, and breathtaking scenery. Keep reading to find the best fit for your trip.
1. Key West Schooner Sunset Sail with Bar & Hors d’oeuvres
At number 1, this cruise offers an elegant way to unwind at sunset. Set sail on a replica of the 1851 Schooner America, which is a real beauty, and enjoy complimentary hors d’oeuvres and drinks including beer, wine, and champagne. The two-hour tour passes by iconic sights like Fort Zachary and Sand Key Lighthouse, with gorgeous views as the sun dips into the Atlantic.
What makes this trip stand out is the timeless sailing experience combined with top-notch hospitality. Reviewers repeatedly mention the crew’s professionalism and the relaxing atmosphere. For around $116, you get a peaceful, scenic ride plus excellent snacks and drinks. Perfect if you’re seeking a romantic sunset or a quiet escape on the water. A typical comment: “A very relaxing and well-run cruise with an exceptional crew.”
Bottom Line: Elegant, scenic, and relaxing — ideal for couples or anyone wanting a classic sailing experience with good food and drinks.
2. Key West Cocktail Cruise Adults Only Sunset Cruise with Open Bar
For around $65, this adults-only cruise delivers a lively and intimate vibe. Climb aboard the 47-foot catamaran to enjoy unlimited South Florida craft beer, California wine, and handcrafted cocktails as the sun sets. The tour lasts about two hours, and the focus is on relaxed socializing with friends or fellow travelers.
What makes this cruise special is the informal open bar combined with scenic views — no need to worry about extra costs, and the boat’s size makes for a cozy, friendly atmosphere. Reviewers love the friendly crew and spectacular sunset views, with one describing it as “a fun, relaxing experience with great drinks and a friendly crew.” It’s best suited for those who want a casual, fun night with plenty of beverages and good company.
Bottom Line: Perfect for adults seeking a social, booze-filled sunset adventure without the crowds.
3. Key West Tiki Bar Sunset Cruise (by the seat)
This small-group cruise is a hidden gem, limited to just six people, making it an intimate and personalized experience. The custom tiki boat is equipped with bluetooth stereo, ice, cups, and a captain, but you bring your own adult beverages and snacks.
During the cruise, the captain points out local landmarks and wildlife, cruising past Sigsbee Key, Sunset Key, and Sunset Pier. The real highlight is the personalized attention and the chance to toast the sunset in a quiet, uncrowded setting. Reviewers highlight the captain’s knowledge and the small size as reasons why this trip feels more like a private boat trip. The chance to take photos of the elusive “Green Flash” is a bonus.
Bottom Line: Best suited for small groups or couples wanting a private, relaxed sunset with a personal touch.
4. Key West Haunted Pub Crawl and Ghost Tour with Free T-Shirt
For those interested in a mix of spooky stories and drinks, this 2-hour haunted pub crawl offers a different twist. Stop at haunted bars, former mansions, and even a former morgue, all while hearing ghost stories from your entertaining guide. Costumed guides and eerie locations make it a lively, spooky experience.
Guests rave about the fun storytelling and the dive into Key West’s darker side, with one reviewer noting how it “made us see ‘Bone Island’ in a different light.” The tour includes visits to some of the most haunted spots in Old Town and a souvenir T-shirt for a keepsake. It’s perfect for history buffs or those who enjoy a good scare with their drinks.
Bottom Line: An entertaining and spooky way to explore Key West’s haunted past, combining history, humor, and a little ghostly fright.
5. Key West Tiki Bar Boat Cruise to Popular Sand Bar
This private, four-hour tour costs about $565 for up to six people, making it a luxury experience. You’ll cruise aboard a Tiki bar boat to a secluded sandbar, with ample time for swimming, sunbathing, or snorkeling. Along the way, you might spot dolphins and turtles, adding to the adventure.
What sets this tour apart is the customized, uncrowded environment — ideal if you’re celebrating a special occasion or want privacy. The captain is knowledgeable about local wildlife and points out sights, making it both fun and educational. Reviewers appreciate the relaxing pace and personal feel, with many saying it’s a perfect way to end a trip.
Bottom Line: Best suited for private groups or couples looking for a luxurious, personalized day on the water.
6. Dinghy Drinking Tour through Key West Waters
For $85 per person, this 3-hour small-group tour takes you through mangrove tunnels to waterfront bars and restaurants. The small dinghy can go into narrow tunnels larger boats can’t reach, offering a unique perspective of Key West’s waterways.
Along the way, you’ll see fish, sea turtles, and seabirds, making it a scenic adventure with plenty of opportunities for swimming. The tour includes stops at 2 to 3 waterfront bars, where you can enjoy drinks and the relaxed atmosphere. Reviewers love the personalized service and the chance to explore hidden spots.
Bottom Line: Great for those looking for a fun, interactive, and scenic water tour with a focus on local watering holes.
7. Key West Signature Sunset Cruise with Open Bar, Food & Music
This popular sunset cruise offers a two-hour sail on a catamaran, complete with an open bar, appetizers, and live music. It’s a lively choice for those who want a festive atmosphere while enjoying the sunset over the Gulf of Mexico.
Guests mention the great vibe, friendly crew, and scenic views. The combination of music and drinks makes it a good choice for celebrating a special occasion or just relaxing with friends. The price of $80 offers good value considering the included food and entertainment.
Bottom Line: Ideal for travelers seeking a fun, musical sunset experience with plenty of drinks and good company.
8. Classic Key West Schooner Sunset Sail with Full Open Bar
This classic schooner experience provides an authentic sailing trip with a full open bar. The two-hour cruise departs from the vibrant Key West Historic Seaport, passing by Mallory Square and Sunset Key, with the chance to catch the famous sunset.
Guests love the timeless charm of the schooner, along with the friendly crew and well-stocked bar. The voyage combines scenic views with the relaxed elegance of traditional sailing. It’s particularly suited for those interested in a more scenic, tranquil experience.
Bottom Line: Best for travelers wanting a traditional sailing vibe combined with the beauty of a Key West sunset.
9. Key West Afternoon Reef Snorkeling with Open Bar
While primarily a snorkeling trip, this tour also features a refreshing open bar. For about $60, you’ll sail out to see coral reefs teeming with tropical fish, then relax with beer, water, and soft drinks after your swim.
The highlight is the combination of underwater adventure and water-based relaxation. Reviewers mention the beautiful reef and smooth ride. It’s well-suited for those who want a mix of activity and leisure, especially if you enjoy snorkeling and drinks.
Bottom Line: A good choice for active travelers who want to combine reef exploration with a chilled waterside experience.
10. Original Key West Pub Crawl: The Best Bars with Free T-Shirt
This lively 2.5-hour guided pub crawl hits several top bars, including Rick’s, Flying Monkeys, and Durty Harry’s. With a free souvenir T-shirt and drinks at each stop, it’s a fun way to sample Key West’s famous bar scene.
Guests enjoy the fun, energetic guides and the chance to see multiple spots in a short time. It’s a great choice for travelers who want to party and socialize. The tour is especially popular among first-time visitors wanting a taste of Duval Street’s nightlife.
Bottom Line: Perfect for those wanting a lively, social experience with a good mix of drinks and bar-hopping.
11. Key West: All-Inclusive Watersports Adventure with Lunch & Beer
This full-day water sports tour is about six hours of fun, including jet skiing, parasailing, and snorkeling. For $179, it offers lunch and draft beer, making it a great value for active travelers who want variety.
Guests often praise the friendly staff and ample time for each activity. It’s ideal for adventure seekers who want to stay busy and enjoy the sea. Keep in mind, it’s a longer tour, so it’s best suited for those with full days available.
Bottom Line: For thrill-seekers wanting an all-day, multi-activity experience with food and drinks included.
12. Sunset Sip and Sail Key West with Open Bar and Live Music
This two-hour sunset cruise combines open bar, live music, and beautiful scenery. The large catamaran offers a comfortable ride, and the music adds a festive touch.
Reviewers mention the friendly crew and the relaxing atmosphere. It’s a good option for those who want a laid-back, fun evening with drinks, music, and a sunset. The mix of entertainment and scenic views makes it a top pick.
Bottom Line: A lively but relaxed option for travelers who want music, drinks, and sunset views in one trip.
13. Schooner Appledore Day Sail with Full Bar in Key West
This daytime schooner sail offers a peaceful, scenic experience aboard a historic two-masted vessel. The trip includes a full bar, and participants can help hoist sails, making it interactive.
The timeless charm of the schooner combined with the beautiful scenery and a well-stocked bar makes this a popular choice. Guests comment on the professional crew and the relaxing vibe. It’s suited for those wanting a scenic, authentic sailing experience with drinks.
Bottom Line: Perfect for history lovers and those seeking a slow, scenic day at sea.
How to Choose Your Drinking Tour in Key West
When selecting a tour, think about your budget, time constraints, and what kind of experience you’re after. For romantic sunsets, the Sunset Sail with Hors d’oeuvres or the Classic Schooner Sunset Sail offer timeless scenery. If you prefer a more lively atmosphere, the Pub Crawl and the Signature Sunset Cruise with music are excellent choices.
Beach lovers and adventure seekers should consider the Sand Bar Tiki Boat or the Water Sports Adventure, which combine activities and drinks. For small groups or privacy, the Tiki boat or the Dinghy Tour are ideal.
Booking early is advised, especially for popular sunset cruises and private tours during peak season. Consider the duration—half-day trips work well if you want a mix of activity and relaxation, while full-day adventures suit those craving variety.
In summary, Key West offers a wide range of drinking experiences, from serene sunset sails to lively pub crawls and private boat trips. For a romantic evening, the Schooner Sunset Cruise or the Appledore Schooner Day Sail stand out. For socializers and groups, the Pub Crawl and the Sunset Sip with Live Music deliver lively atmospheres.
No matter your style, booking your favorite tour early guarantees a memorable, fun-filled time in this vibrant island paradise.