Popular, arty wine bar with 20+ wines by the glass & 200+ bottles, plus cheeses & charcuterie.

Creative New American fare & a broad wine list served in a Victorian mansion with a garden & porch.

Lively joint offers island-inspired fare & margaritas plus a gift shop & live music most nights.

Neighborhood cocktail bar and liquor store offering classic craft cocktails, fine wine, and small bites.

Cozy, laid-back cocktail bar offering classic & updated tiki drinks amid retro South Seas decor.

Coffeehouse offering pastries, bagels, and breakfast dishes, plus wine and beer.

Second floor of the Bull & Whistle Bar featuring a large squared bar, pool tables, games, and a balcony.

Quaint counter-serve doling out salads & housemade pastas, plus cocktails & wood-fired pizzas.

Happening watering hole with a classic-rock playlist, roadhouse decor & a buzzy late-night scene.

Craft cocktails, beer, and live music are on offer in this historic Old Town lounge.

A toast to Old Key West, with a twist of cowboy charm serving mouth-watering BBQ, Southern-inspired favorites, and fresh local seafood.

Easygoing bar offering a diverse menu of cocktails, plus cupcake sushi & familiar snacks.

Funky 2-story debauchery den filled floor-to-ceiling with local paintings, rock n' roll set lists, Key West memorabilia, and a homage to a hunk of Slash's chewed gum

Small upscale hideaway bar with a speakeasy atmosphere and fancy cocktails.

Longtime open-air hangout for seafood complemented by live music & dockside views.

Relaxed garden cottage offering separate menus for breakfast or lunch & dinner, as well as drinks.

Casual bar and grill serving quick bites, cocktails, and music.

Charming tapas bar pairing global small plates with house-specialty sangria in a warm room.