Seven ways to experience Key West like a local

An undeniably warm ambiance lulls you into Santiago’s Bodega, which trades Key West’s typical seafood fare for Mediterranean-style small plates. Swing by for happy hour—happening daily from 3 to 6pm—to throw back half-off wine and fresh sangria with the locals, then stick around for a candle-lit dinner spread that you won’t find on hectic Duval Street. The menu includes more than two dozen tapas. Sure-bets include the seared beef tenderloin that’s drowned in a rich blue cheese butter, and the yellowfin tuna ceviche: big chunks of fish marinated in spicy citrus juice, served chilled with avocado, mango and cilantro.

Part honky-tonk, part dive bar, iconic local hangout Green Parrot Bar proves that the Key West music scene goes deeper than songs about margaritas and cheeseburgers (as infectious as those may be). On any given night, the shed-like venue rocks with live local bands (and a well-worn jukebox) playing everything from New Orleans jazz to indie rock and reggae. Walls adorned with old-school Key West memorabilia round out the island-time vibe and speak to the spot’s nearly 130-year-old history as a beloved local watering hole.

Imbibe in style at First Flight, an off-the-beaten-path charmer housed in the original office of Pan Am Airlines. The microbrewery is seriously Instagram-worthy, with its enchanting courtyard lined with palm trees and lit with strands of twinkling lights. There’s ample wine and locally brewed suds on the menu, but it’s the boozy cocktail list that sets this place apart. Try the Bermuda Triangle, a refreshing mix of gin, St. Germain, lemon and sparkling rosé. Pulling an all-nighter? The Espresso, made with house espresso, vanilla vodka and Kahlua, will have you whirling with the conchs well past closing time.

The Cookie Nookie, Peanut Butter Perversion and Kinky Key Lime Pie are a few of the luscious treats that set the mood at dessert emporium Better Than Sex, which seems to want nothing more than to stuff your face with sweets. The romantic vibe is kicked up a notch with chandeliers, naughty photos on the walls and plush two-seater booths perfect for a Key West date night. Don’t leave without checking out the dessert-forward wine list; including the Yum Yum and Choco-Port, which are served in chocolate- or caramel-rimmed glasses.

If you hit one bar on Duval Street make it Aqua Key West, the neon-hued home of some of the wildest drag shows in town. Intrepid queens pull out all the stops—piling on mounds of hair, donning kooky costumes and lip-synching their hearts out—to remind folks that Key West is nothing without its raucous, proud-as-hell LGBTQ culture. If all the theatrics have you itching to tap into your inner diva, try out some Whitney, Mariah or Cher at karaoke there every Monday through Thursday at 11pm.

Situated in a circa 1829 carriage house, the Red Barn Theater proves that you don’t have to go to the big city to find art that moves you. This 88-seat gem has been ground zero for first-rate theater in Key West for nearly 40 years, whether by spotlighting forward-thinking new works from emerging playwrights or offering fresh takes on classics by folks like Tennessee Williams (who actually graced this stage a few times in the ’40s and ’50s). Check out what’s playing next time you’re in town for an unbeatable shoulder-to-shoulder culture fix with the locals. Shows start back up in October!

Yes, vacation is all about sleeping in, but treat yourself to at least one early morning so you can catch the sun come up over Bight Marina, located in the Historic District. Light fills the sky to reveal deep aquamarine waters at their stillest, yachts of every size parked along the docks and local fisherman prepping their vessels before heading out to sea for that day’s catch. It’s the kind of experience that’ll have you dreaming of Key West long after you leave—and perhaps the number one reason that‘ll have you itching to get back.