Savannah’s secret wine window is tucked inside this chic courtyard

Lester's in Savannah

If strolling Savannah’s historic oak-lined streets and peeking through wrought-iron gates at secret gardens isn’t charming enough, the city has a courtyard with a hidden way to have a drink in style. It’s not a bar — it’s a wine window. And it’s drawing locals and visitors in the know.

In the architectural spirit of Florence, Italy’s famed small portals that serve wine by the glass (also known as “buchette del vino”), this petite-and-playful feature can be found in the courtyard of Lester’s at The Douglas, a luxe boutique hotel housed in a circa-1800s townhouse on Oglethorpe Avenue.

Lester’s, which offers tinned fish, a raw bar and a caviar menu, debuted earlier this summer and is helmed by Jacques Larson, the Charleston-based chef behind Lowcountry favorites The Obstinate Daughter on Sullivan’s Island and Wild Olive on John’s Island.

On the menu, expect a tight list of red, white, bubbles, rosé, and orange wines around $14 to $19 per glass, and bottles ranging from the 2024 Vinhos Fitapreta Touriga Vai Nua Alentejo for $58 to the NV Marie Courtin “Resonance” Blanc De Noirs Extra Brut Champagne for $190.

Beyond wine, the bar window offers several martini variations, including one topped with a seasonal mignonette, along with creative cocktails and non-alcoholic options. (Tip: to-go cups are available thanks to Savannah’s open-container policy.)

The courtyard opens daily at 5 p.m., with reservations available via Resy. 

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