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

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

Dog-friendly bar with live music and an outdoor setting, featuring a full bar and Garbo's food truck.

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

Seafood-focused American eatery set in an 1884 house with wraparound balconies for people-watching.

Offers Argentinian grass-fed steaks, seafood, crafted cocktails, and a list of Argentine wines.

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

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

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

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

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

A great KW staple with attached butcher shop, open to veterans and public alike.

Funky bowling alley-inspired taco & beer establishment with board games, vintage signage, and a ceiling lined with album covers.

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

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

Open-air, beach-style bar and grill serving burgers, seafood, and other pub grub, plus live music.

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

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

Relaxed lounge providing kava, elixirs, and non-alcoholic drinks, plus live music and events.

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

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

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

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

A lively, open‑air spot just off Duval Street, serving up daily live music, Tex‑Mex comfort food & empanadas, plus craft cocktails and happy hour deals until late into the night