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Key West Pub crawls & bar tours

Our most recommended Key West Pub crawls & bar tours

Key West: 2.5-Hour Duval Street Pub Crawl

1. Key West: 2.5-Hour Duval Street Pub Crawl

Come along and do the pub crawl down Duval Street, Key West. This street is famous for its party scene, with the bars always rocking day and night on this small island. Throughout your pub crawl you will experience some of the most famous and entertaining drinking establishments in the Florida Keys. This 2.5-hour event happens on the world famous Duval Street. Everyone will have a choice of a domestic beer or mixed drink at all five bars visited, and you will also receive a free souvenir t-shirt to commemorate the event. Experience all the sites and bars of Key West with your "professional enablers" as you embark on your party in paradise. Whether it's the casual Keys atmosphere, live music, or Caribbean drinks you are after, your crawl is sure to be an adventure to remember.

Orlando: Mango's Tropical Cafe Dinner and Show

2. Orlando: Mango's Tropical Cafe Dinner and Show

Experience authentic flavor, dynamic performances, and much more at Orlando's hottest destination in nightlife and entertainment: Mango's Tropical Café.  Dine and dance in an energy that's unmatched and electric, all in the heart of the city's famous International Drive. Enjoy a family-friendly dinner and show, featuring paramount live entertainment including a Michael Jackson tribute, a Brazilian Samba, Cuban Conga, and other Latin-inspired numbers throughout the entire breathtaking venue. Mango's live band promises to get you on your feet with lively and passionate authentic Latin music featuring congas, bongos, horns, 80's, 90's, today's hits, and more.  Savor a three-course gourmet menu of fresh "Floribbean" cuisine. Specializing in Latin and Caribbean comfort foods, as well as American favorites, Mango's serves up a one-of-a-kind dining experience for every person at your table. Menu: Starter choice of: • Caesar salad • Tomato bisque Entree choice of: • Mango's Churrasco Steak ($15 upcharge) • Roasted Margarita Chicken • Braised short ribs • Salmon al Limon • Plant-based penne bolognese All entrees, except the plant-based penne, are served with yellow rice, Cuban-style black beans, and plantains. Dessert choice of: • Mango coconut bread pudding • Chocolate Ecstasy

Key West: Windjammer Sunset Cruise with Full Open Bar

3. Key West: Windjammer Sunset Cruise with Full Open Bar

Set off in search of the perfect sunset aboard the Appledore II, a 2-masted wooden schooner. Sip on your favorite drink and enjoy this scenic sunset tour that also takes you past some of Key West’s famous sights. With the painted sky as the backdrop, your sunset sail takes you past Key West’s historic seaport, Mallory Square’s sunset celebration, the navy mole where the big ships dock, and the civil war era Fort Zachary Taylor. Take in the sights while enjoying a glass of champagne or boutique wine, home-made sangria, an ice-cold beer, soft drinks, or something from the full cocktail bar. Feel a sense of adventure as the crew hoists the sails and participate in this tradition by helping to raise the sails. When the sun begins its descent, your captain will take the boat to the perfect spot to maximize the setting sun views.

Key West: Hemingway's Life and Local Food Walking Tour

4. Key West: Hemingway's Life and Local Food Walking Tour

Discover the life of Ernest Hemingway while he lived in Key West on this guided walking tour. Uncover where the author lived, worked, and played. Stop to try three different samples of Key West cuisine as you walk.  Meet your guide at the front gate of the elegant residence where the author lived during the 1930s, Hemingway House. Make your way to get some local treats to help energize you for your walking tour. Try some delectable food like grilled chicken street tacos, conch fritters, and key lime pie. Find out where he watched and refereed boxing matches. See where he kept his boat the Pilar. Capture pictures of the bookstore where his books were sold. Stroll by his first apartment in Key West where he finished writing “A Farewell to Arms.” Make another stop to for some food before visiting where the author used to catch the train. Observe where he used to fish and charter boats. Finally, head to Sloppy Joes which was a favorite watering hole for the writer. 

Key West: Bone Island Haunted Pub Crawl

5. Key West: Bone Island Haunted Pub Crawl

Join us for a ghostly guided walking tour into the heart of old town Key West's most haunted bars. On this haunted pub crawl you will experience why Key West is consistently ranked as one of the top five most-haunted cities in America. Crawl along as you delve into some of the more spirited pubs of Old Town. You'll discover Key West's history of cursed treasure, voodoo, murder, suicide, haunted mansions, unexplained deaths, and more. Your professional "ghost host" will introduce you to the darkest side of "Bone Island" with unbelievable stories of Key West's sinister past. You will receive our signature T-shirt to commemorate the event and cocktails are available for purchase along the way. The crawl ends in the heart of downtown Key West where you will be free to explore more.

Key West: Private Tiki Bar Party Boat

6. Key West: Private Tiki Bar Party Boat

Party with up to five friends on a boat with a Tiki bar in beautiful Key West. Let your captain take you to an excellent swimming hole for a 2-hour afternoon party. Bring your favorite cocktail, a couple of snacks and some fun-loving friends. Keep your drinks cool with the cooler with ice. Crank-up your favorite tunes on the Bluetooth Stereo. Enjoy some drinks and leave the driving to your captain. Stay in the shade with a Tiki thatched roof. Keep afloat and soak in the sun with the 6' x 18' floating mat. Have use of a walk-in bathroom.

Key West: Off-Duval Cocktail Crawl

7. Key West: Off-Duval Cocktail Crawl

This craft cocktail crawl leads you through the side streets of Key West visiting a fun variety of locally-loved watering holes. Sample fun craft cocktails and tasty gourmet bites on this 3-hour upscale pub crawl. Visit over 5 establishments, ranging from a sleek bar within a historic hospital, a microbrewery inside the birthplace of PanAm, a tiki bar, and more. This tour veers vacationing drinkers off the infamous Duval Street into some of the city’s best and most locally-loved bars to sample fresh spins on old classics. Discover the iconic stories behind Key West’s signature drinks, like the Hemingway Daiquiri, and explore the sights, sounds, and “intoxicating” flavors of the tiki era. This bar hop is about getting off the touristy Duval Street and into more local lounges. Between tastings, you will stroll the charming side streets alongside Duval with protected, wild chickens. Your fun and friendly local guides will share bits of the town's colorful past and historical landmarks. Explore Old Town with recommendations on restaurants, attractions, and entertainment. Return home with exclusive recipes, ensuring that you can enjoy memories from this tour for many years to come.

Key West: Haunted Pub Crawl Walking Tour

8. Key West: Haunted Pub Crawl Walking Tour

Take a look at the Key West's dark past on a haunted pub crawl walking tour. From the island’s demonic dolls to one infamous case of necrophilia, not everything is glamorous in paradise. Hear all these stories with a drink in your hand as you make your way from bar to bar over an evening. First, head to Captain Tony’s Saloon — Key West’s most eccentric bar with bras on the ceiling and fake bodies beneath the floors. The peculiar tree in the middle of the bar has stained the ground it sits on, its victims still roaming the stools and bottles. Then make your way to Wine-O Bar & Lounge — a staple of Key West’s largest building, La Cocha Hotel. But with great praise comes great tragedy, as being the tallest building makes you a prime candidate for suicide. And with tragic suicides come tragic hauntings. Next, head over to The Roost, which serves some of the best cocktails in Key West. It's also neighbor to one of America’s most haunted city blocks. There, see Key West Theater, a place that houses many shows but used to house children’s screams, and the Artist House, which used to be the home to a cursed doll. Learn about how the Dean-Lopez Funeral Home was once home to a lover’s obsession gone wrong and the lengths he took to bring back the dead. Finally, stroll over to the old-fashioned Old Town Tavern & Beer Garden. You might find the spirit of Ernest Hemingway frequenting it, since his Key West home is right down the street. Hear stories about each haunted location, one drink at a time.

Homestead: Sunset Cruise, Buffet Dinner, and Drinks

9. Homestead: Sunset Cruise, Buffet Dinner, and Drinks

Expereince a top Key West attraction with this sunset cruise day trip. Travel from your accommodation in Homestead to the comfortable boat by air-conditioned bus and savor a delicious buffet with unlimited well drinks, draft beer, wine, and soft drinks. Be picked up from the comfort of your accommodation in Homestead and relax on the transfer in a climate-controlled bus. Hop aboard a spacious ship and partake in the fresh flavors of a tropical-themed buffet. Sip margaritas, rum runners, wine, or beer. Relax with someone you love as you watch the sun dip below the horizon over the stunning landscapes of Key West. Take in views of the sea, the waterfront, and the sky's warm glow. Live music provides a festive atmosphere. Treat yourself to a premium drink at the cash bar. Return to the bus and transfer back to your hotel at the end of your sunset experience.

Other Sightseeing Options in Key West

Want to discover all there is to do in Key West? Click here for a full list.

What people are saying about Key West

My girlfriend and I would 100% recommend the "pub crawl"!! It was fun, you get to meet people and our guide did a great job. She was in a great mood, motivated, funny and was able to bring us closer to the history of keywest!!! Great experience for us!!!

It was all good everyone was friendly and helpfull in every way. The show was wonderful and the music was great !

Excellent service the girl served us was soooo nice Amazing shows, food was so Good

Great pub crawl through Key West's prettiest bars. Tasty drinks included

JD was friendly; stories believable. Entertaining and informative.