The Deck, the Sunset, and a Wine List That Backs It Up
Old Town (Waddell Ave) · Key West · New American / Caribbean · Visit Website ↗
Updated February 2026
Reviewed by the RagingWine Tasting Desk · February 8, 2026
RagingWine reviewed Louie's Backyard’s wine list and gave it The Rager — RagingWine’s Vibe-Check rating. How RagingWine reviews wine lists →
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Wingman Metrics
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. The Afterdeck Bar offers curated wines with creative cocktails in an alfresco setting that doubles 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.
The Bottom Line
Louie's Backyard is the rare Key West restaurant that has been famous for decades and still earns it every night. The back deck alone is worth the trip. The wine list and food make it one of our favorites on the island.
Historic Seaport · Key West · American / Seafood
Schooner Wharf is a legitimately great bar — just not a wine bar. Order a beer, get the shrimp, watch the sunset, and if you must have wine, grab the Sterling Sauv Blanc and call it a day.
Grocery Store
Fair
Basic Stemmed
MIA
Set & Forget
Acceptable
Duval Street / Old Town · Key West · Seafood / New American
Bagatelle is doing more with wine than most restaurants in the Keys bother to attempt, and for a tourist-heavy Duval Street address, that matters. The markups are real and the list skews safe-prestige, but if you're in Key West and want a proper bottle with your lobster, this is where you go.
Solid Range
Steep
Basic Stemmed
Rotating Cast
Set & Forget
Acceptable
Fleming Street / Old Town · Key West · Seafood / Raw Bar
Thirsty Mermaid is a Wild Card in the best sense — a no-frills raw bar that somehow sourced a wine list worthy of a much fancier room. The markups on the high-end bottles are steep and there's no wine program energy to speak of, but the Cava-and-oysters combination alone is worth the stop.
Small but Thoughtful
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Stock Island / Oceans Edge Resort · Key West · Seafood / Elevated American
Matt's is the wine list equivalent of a reliable vacation — it won't blow your mind, but it won't ruin your evening either. Order the Albariño, watch the boats, and save the wine exploration for somewhere that's actually trying.
Crowd Pleasers
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
North Roosevelt Boulevard / Waterfront · Key West · Hotel Bar / American
The Roost is a hotel bar doing more than the minimum — there's real range here and a few genuinely good picks if you know where to look. Just go in expecting to pay for the waterfront zip code, and you'll have a fine time.
Solid Range
Steep
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
Simonton Street / Old Town · Key West · Cafe & Bakery
Moondog isn't a wine destination, and it doesn't pretend to be — but it offers a surprisingly considered little list at prices that don't insult your intelligence, which puts it well ahead of the tourist-trap cafes clustered around it. If you're in Old Town and want a glass with your morning or a light lunch, there are worse decisions you'll make in Key West.
Small but Thoughtful
Fair
Basic Stemmed
Willing but Green
Set & Forget
Acceptable
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