Key West
Nightlife & Bars

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Our most recommended Key West Nightlife & Bars

Key West: Sunset Cruise with Buffet Dinner and Open Bar

1. Key West: Sunset Cruise with Buffet Dinner and Open Bar

Climb aboard "The Party Cat" for a wonderful 2-hour cruise around the harbor.   Enjoy a freshly prepared tropical food buffet in an enclosed air-conditioned dining room. Choose from dinner options such as roast pulled pork in mojo sauce, deep fried sweet plantains, black beans and rice, marinated grilled chicken, fried fish, mixed vegetables, mashed potatoes, pasta with mini shrimp and Cuban bread and butter. Sip on your choice of tipple — margaritas, rum runners, champagne, beer, wine or spirits. After dinner, stroll upstairs to the upper deck for live music. Dance the night away or simply listen to the beat as you watch the sun set over the horizon into the Gulf of Mexico. Witness the beautiful display of colors across the night sky.

Key West: Sunset Sailing Trip with Open Bar, Food and Music

2. Key West: Sunset Sailing Trip with Open Bar, Food and Music

Join a sailing experience to get you closer to the sunset than ever before. Set sail from the historic sea port of Key West and head straight out to sea for a cruise with unobstructed views of the sunset on the horizon. During the cruise, enjoy an unlimited open bar, with a wide variety of drinks on offer including rum runners, Champagne, margaritas, and draft beer. Taste a selection of finger foods, ranging from Swedish meatballs, veggie treats, cheese and crackers, pita and hummus, and meat and veggie platters. You will be sailing on one of Key West's newest sailing catamarans, the Sandie Cat. This vessel has capacity for up to 149 passengers across 3 decks, so there will always be plenty of room onboard. Grab a drink, head to the upper deck, and dance to live music as you watch the sun go down. The captain and crew will even let you help raise the sails and you can ask to have a picture taken driving the boat.

Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat

3. Key West: 4-Hour Private Sandbar Cruise on a Tiki Bar Boat

Explore the turquoise waters of Key West and the Florida Keys on a sandbar cruise on a floating tiki bar boat for a fun and private day out on the water with friends and family. Bring your own food and drinks and party like a local. Escape the crowds and explore the gorgeous waters of the Florida Keys as you make your way to the pristine sandbars that lie offshore. There’s a good chance you'll spot rays, turtles, fish, and even dolphins. For an unforgettable day out, bring your swimsuit, towel, sunscreen, snacks, and drinks (alcohol welcomed). Enjoy a floating mat, foam noodles, and a Bluetooth stereo for even more fun.

Key West: 2.5-Hour Duval Street Pub Crawl

4. 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.

Key West: Haunted Pub Crawl Walking Tour

5. 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 neighbors to one of America’s most haunted city blocks. There is Key West Theater, a place that houses many shows but used to house children’s screams. And there is 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 Hemmingway frequenting it, since his Key West home is right down the street. Hear stories about each haunted location, one drink at a time.

Key West: Drag Queen Guided Pub Crawl with Sing-a-Longs

6. Key West: Drag Queen Guided Pub Crawl with Sing-a-Longs

Meet your guide for the night, a world-class drag queen, at the award-winning lounge, Aqua Bar and Nightclub at 711 Duval St. in Key West. Grab a cocktail and mingle with your fellow crawlers as you await the ring of the ‘bitch bell’ to announce the kick-off of the tour. First, follow your guide through the vibrant streets of Key West and prepare to sing and dance your way through the city as you learn how to party like a true queen. Now you know how to behave like a queen it's time to be treated like one too — skip to the front of the line at every bar and pub along the crawl. Then, spend the night at a number of Key West's best bars and clubs, drink delicious and reasonably priced cocktails, laugh with your fellow crawlers, dance like a queen, and experience how the other half lives. Enjoy a fun-filled tour that's perfect for bachelorette parties, birthdays, and other memorable events.

Key West: Bone Island Haunted Pub Crawl

7. Key West: Bone Island Haunted Pub Crawl

"Cayo Hueso" in Key West, as it was originally named, translates to "Bone Key" or "Bone Island". 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, and after 3 haunted pubs you will be issued a souvenir t-shirt before being released into the night.

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

8. 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: Private Tiki Bar Party Boat

9. 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.

Miami/Fort Lauderdale: Sightseeing Pass for 35+ Attractions

10. Miami/Fort Lauderdale: Sightseeing Pass for 35+ Attractions

Enjoy Miami and Fort Lauderdale with access to over 35 attractions, tours, and wild adventures all over the coastal heart of South Florida, including the best outdoor beach activities, downtown outings, and wildlife experiences in Miami, Fort Lauderdale, and Key West. With the option to select 2, 3, 4, 5, or 6 attractions, take advantage of full admission to attractions, saving you up to 55% of total visitation costs and no fixed start date. Recommended for visitors with limited time for sightseeing who want to visit only a few of the most popular attractions. Visit South Beach for some well-deserved time to recline and tan, then dive into your choice of watersports, like kayaking, paddle-boarding, parasailing, and snorkeling. Travel with ease downtown on a Hop-On, Hop-Off Bus tour to check out Bayfront Park or Morningside Park. Plus, enjoy exclusive access to activities and discounts in luxurious Key West. With centuries of Spanish and Caribbean influences, the tropical delights of Latin America and Cuba are everywhere in Miami. Grab a Café Cubano, Cortadito, or a Mojito at authentic restaurants, then dance the night away at salsa clubs and beachside bars. Plus save with discounts to restaurants, bars, and retail stores. Don't let the NFL’s Miami Dolphins be your only exposure to Miami's vibrant wildlife! See Florida’s natural icons, like the opulent and pink residents of the Flamingo Gardens and meet the diverse marine specimens at the Miami Seaquarium. Step deep into the wild of the Everglades on the hunt for alligators, with one of many Air Boat tours. Attractions: • Miami Seaquarium • Everglades Holiday Park - Airboat Tour • Flamingo Gardens • Wild Florida • Key West Yoga Train • Sunrise PaddleBoards • Sunset Watersports • Federico Empire Boutique Cigar Factory Tour • FunDimension - Family Entertainment Center • Ripley's Believe It or Not! • Coral Springs Museum of Art • Fort Lauderdale Historical Society - Three Museum Tour • Zoo Miami • The Museum of Illusions Bus Tours + Boat Cruises: • Big Bus Classic Hop-on Hop-off Miami Tour Ticket - Beach and City Routes • Big Bus Panoramic Night Tour • Key West Day Trip - Amadeo Travel • Fiesta Cruises • Jungle Queen Sightseeing • Thriller Speedboat Ride Walking and Wheeled Tours: • Florida Revealed - Fort Lauderdale • Fort Lauderdale Historical Society • Little Havana Adventure • Picture Perfect Photo Tour • The Art Experience - Little Haiti Adventure • Wynwood Art Walk Tour • Bike and Roll - Hybrid Bike Rental • Segway Fort Lauderdale • Sobe Rides Art Deco Pedicab Tour • Sunset Watersports Bike Rental • Scavenger Hunts - Miami

Frequently asked questions about Key West Nightlife & Bars

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Other Sightseeing Options in Key West

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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!!!

The sunset cruise and dinner was amazing. We saw a beautiful sunset along with some great music and dance. The entire crew including the band was great. Thank you for the experience

Food was good, drinks as excepted but entertainment was great which kept the party going!

Puddingtane was amazing! She was hysterical and kept me laughing the whole time.

The food was very good, captain and staff were fun. Entertainment was the best