Louie's Backyard

Louie's Backyard has been a Key West institution since 1971, and the back deck is the reason. Multi-tiered outdoor seating suspended above the Atlantic, so close to the turquoise water you could theoretically drop a bread roll into the ocean. The restored Victorian house gives it a sense of place that the chain restaurants on Duval will never touch. Executive Chef Doug Shook has maintained the kind of New American-Caribbean menu that rewards both the adventurous and the traditional diner.

Over 100 selections and a by-the-glass program that does not treat casual drinkers as afterthoughts. The Afterdeck Bar offers curated wines with creative cocktails in an alfresco setting that doubles as one of the best pre-dinner spots on the island. The main dining list goes deep enough to reward exploration, with fair pricing on most bottles given the setting. If you are going to spend on wine anywhere in Key West, this is where the glass-to-view ratio pays off.

Snapper ceviche to start. Grilled octopus if they have it. The local catch changes daily and the kitchen handles every protein like it came off the boat that morning. Louie's also does not skimp on the land side: steaks, lamb chops, and a Key lime pie that ends the meal exactly right. Lunch is the more casual option and equally strong. The upstairs dining is more relaxed if you want a lighter touch.

Arrive for a late afternoon drink at the Afterdeck Bar. Watch the sunset. Move to the main dining room for dinner. This two-act experience is one of the best evenings you can have in Key West, and the wine list supports both halves. Open Monday through Sunday, 11:30 AM to 2:30 PM and 5:00 PM to 9:00 PM. Call (305) 294-1061 for reservations.