The Florida Keys
We’ve compiled the best of the best in The Florida Keys - browse our top choices for the top things to see or do during your stay.
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1. C&C Wood Fired Eats
While it's only open till 10, it's still the place to see and be seen. It's dark and a little mysterious, and the wine, wood-fired...
While it's only open till 10, it's still the place to see and be seen. It's dark and a little mysterious, and the wine, wood-fired pizzas, cheese pairings, meats, and fondues are five-star worthy. Sit at the bar, on a couch, or at a high-top, and be transported to somewhere other than a typical, tropical Keys venue. The daily happy hour offers a "pizza and pitcher" special that's a hit with locals.
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2. Aqua
Old TownKey West's largest gay bar, Aqua hosts karaoke contests, dancing, and live entertainment at three bars, including one outside on the patio. For an evening...
Key West's largest gay bar, Aqua hosts karaoke contests, dancing, and live entertainment at three bars, including one outside on the patio. For an evening like no other, come see the Aquanettes at their "Reality Is a Drag" show.
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3. Bourbon Street Complex
Old TownPick your entertainment at the Bourbon Street Complex, a club within an all-male guesthouse. There are 10 video screens along with dancers grooving to the...
Pick your entertainment at the Bourbon Street Complex, a club within an all-male guesthouse. There are 10 video screens along with dancers grooving to the latest music spun by DJs at the Bourbon Street Pub.
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4. Breezers Tiki Bar and Grille
Mingle with locals over cocktails and catch amazing sunsets from the comfort of an enclosed, air-conditioned bar. Floor-to-ceiling doors can be opened on cool days...
Mingle with locals over cocktails and catch amazing sunsets from the comfort of an enclosed, air-conditioned bar. Floor-to-ceiling doors can be opened on cool days and closed on hot days. It's located at the Key Largo Bay Marriott Beach Resort.
103800 Overseas Hwy., Key Largo, Florida, 33037, USA305-453–0000 -
5. Capt. Tony's Saloon
Old TownWhen it was the original Sloppy Joe's in the mid-1930s, Hemingway was a regular. Later, a young Jimmy Buffett sang here and made this watering...
When it was the original Sloppy Joe's in the mid-1930s, Hemingway was a regular. Later, a young Jimmy Buffett sang here and made this watering hole famous in his song "Last Mango in Paris." Captain Tony was even voted mayor of Key West. Yes, this place is a beloved landmark. Stop in and take a look at the "hanging tree" that grows through the roof, listen to live music seven nights a week, and play some pool.
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6. Caribbean Club
Walls plastered with Bogart memorabilia remind customers that the classic 1948 Bogart-Bacall flick Key Largo has a connection with this worn watering hole. Although no...
Walls plastered with Bogart memorabilia remind customers that the classic 1948 Bogart-Bacall flick Key Largo has a connection with this worn watering hole. Although no food is served and the floors are bare concrete, this landmark draws boaters, curious visitors, and local barflies to its humble barstools and pool tables. But the real magic is around back, where you can grab a seat on the deck and catch a postcard-perfect sunset. Live music draws revelers Thursday through Sunday.
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7. Durty Harry's
Old TownThis megasize entertainment complex is home to eight different bars and clubs, both indoor and outdoor. Their motto is "Eight Famous Bars, One Awesome Night,"...
This megasize entertainment complex is home to eight different bars and clubs, both indoor and outdoor. Their motto is "Eight Famous Bars, One Awesome Night," and they're right. You'll find pizza, dancing, live music, Rick's Key West, and the infamous Red Garter strip club.
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8. Green Parrot Bar
Old TownPause for a libation in the open air and breathe in the spirit of Key West. Built in 1890 as a grocery store, this property...
Pause for a libation in the open air and breathe in the spirit of Key West. Built in 1890 as a grocery store, this property has been many things to many people over the years. It's touted as the oldest bar in Key West and the sometimes-rowdy saloon has locals outnumbering out-of-towners, especially on nights when bands play.
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9. Hog Heaven
Windley KeyCome by boat or car to this oceanfront restaurant and sports bar where you can soak in the views dockside or relax in the air-conditioning....
Come by boat or car to this oceanfront restaurant and sports bar where you can soak in the views dockside or relax in the air-conditioning. Munch on fresh fish sandwiches or barbecue dishes while you shoot pool, catch the big game on large flat-screens, or dance to a live band or DJ. Late night can get a bit wild and loud.
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10. Hog's Breath Saloon
Old TownBelly up to the bar for a cold mug of the signature Hog's Breath Lager at this infamous joint, a must-stop on the Key West...
Belly up to the bar for a cold mug of the signature Hog's Breath Lager at this infamous joint, a must-stop on the Key West bar crawl. Live bands play daily 1 pm–2 am (except when the game's on TV). You never know who'll stop by and perhaps even jump on stage for an impromptu concert (can you say Kenny Chesney?).
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11. Island House Café + Bar
Old TownPart of a men's resort, Island House Café + Bar serves frozen and other cocktails along with creative cuisine in tropical gardens with a pool...
Part of a men's resort, Island House Café + Bar serves frozen and other cocktails along with creative cuisine in tropical gardens with a pool where clothing is optional. It is open 24 hours.
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12. LaTeDa Hotel and Bar
Old TownThis venue hosts female impersonators (catch Christopher Peterson when he's on stage) and riotously funny cabaret shows nightly in the Crystal Room Cabaret Lounge ($)....
This venue hosts female impersonators (catch Christopher Peterson when he's on stage) and riotously funny cabaret shows nightly in the Crystal Room Cabaret Lounge ($). There is also live entertainment nightly, featuring a variety of local stars including the ever-popular Debra in the ultracool piano bar.
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13. Lorelei Restaurant and Cabana Bar
Upper Matecumbe KeyA larger-than-life mermaid guides you to the kind of place you fantasize about during those long, cold winters up north. It's all about good drinks,...
A larger-than-life mermaid guides you to the kind of place you fantasize about during those long, cold winters up north. It's all about good drinks, tasty pub grub, and beautiful sunsets set to live bands playing island tunes and light rock nightly. Dining is all outdoors, on a deck or under the trees. Service is slow, sometime even nonexistent.
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14. Mangoes
Old TownOn a busy corner right on bustling Duval Street, it's the perfect spot for people-watching and being part of the action. Find a seat at...
On a busy corner right on bustling Duval Street, it's the perfect spot for people-watching and being part of the action. Find a seat at the bar, especially at happy hour, for half-price appetizers and drink deals.
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15. Margaritaville Café
Old TownA youngish, touristy crowd mixes with aging Parrot Heads. It's owned by former Key West resident and recording star Jimmy Buffett, who has been known...
A youngish, touristy crowd mixes with aging Parrot Heads. It's owned by former Key West resident and recording star Jimmy Buffett, who has been known to perform here. The drink of choice is, of course, a margarita, made with Jimmy's own brand of Margaritaville tequila. There's live music nightly, as well as lunch and dinner.
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16. Pier House
Old TownThe party here begins at the Beach Bar with live entertainment daily to celebrate the sunset on the beach, then moves to the funky Chart...
The party here begins at the Beach Bar with live entertainment daily to celebrate the sunset on the beach, then moves to the funky Chart Room. It's small and odd, but there are free hot dogs and peanuts, and its history is worth learning.
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17. Schooner Wharf Bar
Historic SeaportThis open-air waterfront bar and grill in the Historic Seaport district retains its funky Key West charm and hosts live entertainment daily. Its margaritas rank...
This open-air waterfront bar and grill in the Historic Seaport district retains its funky Key West charm and hosts live entertainment daily. Its margaritas rank among Key West's best, as does the bar itself, voted Best Local's Bar six years in a row. For great views, head up to the second floor and be sure to order up some fresh seafood and fritters and Dark and Stormy cocktails.
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18. Skipper's Dockside
There's a fun place in the heart of Key Largo, and marina views are just one of its many charms. Sit outside under the tiki,...
There's a fun place in the heart of Key Largo, and marina views are just one of its many charms. Sit outside under the tiki, or in a brightly colored Adirondack chair by the fire pits, or inside amid driftwood walls and prize catches. No matter: what you'll remember is the fresh, everything-made-in-house food.
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19. Sloppy Joe's
Old TownThere's history and good times at the successor to a famous 1937 speakeasy named for its founder, Captain Joe Russell. Decorated with Hemingway memorabilia and...
There's history and good times at the successor to a famous 1937 speakeasy named for its founder, Captain Joe Russell. Decorated with Hemingway memorabilia and marine flags, the bar is popular with travelers and is full and noisy all the time. A Sloppy Joe's T-shirt is a de rigueur Key West souvenir, and the gift shop sells them like crazy. Grab a seat (if you can) and be entertained by the bands and by the parade of people in constant motion.
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20. The Garden of Eden
Old TownPerhaps one of Duval's more unusual and intriguing watering holes, the Garden of Eden sits atop the Bull & Whistle saloon and has a clothing-optional...
Perhaps one of Duval's more unusual and intriguing watering holes, the Garden of Eden sits atop the Bull & Whistle saloon and has a clothing-optional policy. Most drinkers are lookie-loos, but some actually bare it all, including the barmaids.
224 Duval St., Key West, Florida, 33040, USA305-396–4565
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