🔥The Rager

The Little Pearl

The Quiet Corner of Key West That Gets It Right Every Time

Old Town (Olivia Street) · Key West · Coastal Fine Dining

Prix FixeWine ProgramDate NightTop Pick

Reviewed February 8, 2026

Wingman Metrics

List VarietyDeep & Eclectic
MarkupFair
GlasswareVarietal Specific
StaffKnowledgeable & Friendly
Specials & DealsActive Program
Storage & TempProper

The Setup

The Little Pearl sits at the corner of Olivia and Elizabeth, a deliberate distance from the Duval Street chaos. That placement tells you everything. This restaurant is not trying to grab walk-in traffic. It is trying to feed people who care. The format is a four-course prix fixe tasting menu that changes monthly, built around whatever the local boats bring in and whatever is at peak season. We first came here in 2019. We confirmed it in 2020. Confirmed again in 2024. And again in 2025. It has not missed once.

The Wine List

About fifteen wines by the glass and six half-bottle selections, which is exactly the right size for a tasting-menu restaurant. The list favors coastal whites and lighter reds that work with the seafood-forward menu. Bottles under $50 are available without feeling like afterthoughts, and the premium selections (Burgundy around $95, Oregon Pinot Noir at $98) are priced fairly for the quality. This is a wine program that was built by someone who eats here, not just someone who orders for here.

The Food

Each course builds on the last. You might start with a chilled crab presentation or a tuna crudo that barely needs the sauce underneath it. The mains rotate but often feature local grouper, swordfish, or the signature lobster, shrimp, and crab pot pie that has become a quiet legend on this island. Desserts do not mail it in. The kitchen treats the last course like it matters as much as the first.

The Details

Open seven nights a week, 5 PM to 9 PM. Reservations highly recommended and required for five or more. Same owners as The Thirsty Mermaid, which tells you they understand hospitality at every price point. A 4.9 on OpenTable from over 3,000 diners does not happen by accident.

🔥 The Bottom Line

The Little Pearl is the restaurant that makes you realize Key West has a real food scene, not just a tourist one. Excellent wine list, flawless tasting menu, and the kind of quiet confidence that only comes from doing it right for years. This is our number two, and some nights it fights for number one.

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