Lola's Bistro
The BYOB Secret That Changes Everything
Old Town · Key West · Italian-Eclectic / BYOB
Reviewed February 8, 2026
Wingman Metrics
The Setup
Lola's Bistro sits at 728 Simonton Street, and unless someone tells you about it, you will walk right past. No flashy signage. No Yelp-bait patio. Just a candlelit room with about ten tables, an open kitchen, and Chef Richard working with the kind of focus that makes you lower your voice. This is reservation-only, two seatings per night, and BYOB with no corkage fee. Cash, check, or Venmo. No printed menu. The chef tells you what he's making tonight, and you say yes.
Why Wine Lovers Should Care
Here is the move that makes Lola's a Rager for wine people: Key West has two excellent wine shops on the island. You walk in that afternoon, tell them where you're eating, and they build you a pairing for a fraction of what any restaurant would charge. You show up to dinner with a bottle of Barolo and a crisp Vermentino, and the chef brings an opener. No $25 corkage. No markup. No judgment. For a wine lover in Key West, this is the perfect situation. You get a world-class meal with exactly the wine you want at retail price. That combination does not exist anywhere else on this island.
The Food
The menu changes daily but always features four starters and four entrees. Scallops seared with precision. Duck that pulls apart with no resistance. Lobster ravioli that makes you forget you're in the Keys. Hog fish so fresh it probably swam past Mallory Square that morning. Every plate comes out of that open kitchen like it matters personally to the person who made it. Because it does.
The Details
Starters run $12 to $18, entrees $28 to $38. Book at least two weeks out, especially in season. Call (305) 204-4457 or DM on Instagram @lolasbistro_keywest. Bring your wine. Bring cash. Bring someone you want to have a real conversation with. This is not the kind of place where you check your phone.
🔥 The Bottom Line
Lola's Bistro is the best-kept BYOB secret in Key West. Bring your own bottle, let the chef cook, and have the kind of meal that makes you rethink what dining out can be. This is our number one.
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