Checkmate & ChillEvents

Every Thursday
Whether you’re a seasoned strategist or simply looking for a fun night out, gather at Little James for chess, board games, cocktails, and great conversation. Come challenge a friend, meet someone new, or simply settle in for an evening in Savannah’s neighborhood living room.

Tall frosted glass filled with crushed ice and a yellow-purple flower garnish on a colorful game-board surface (Monopoly-like).

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Savannah Girl Group

Meet new people, share ideas, and become part of Savannah's growing community through Savannah Girl Group at Little James.

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People socialize around tables in a bright cafe-like room with large hanging lamps and green-framed windows behind them.

Monday Pour

A monthly wine ritual beginning with a complimentary tasting on the first Monday, with featured bottles offered at half-off every Monday after.

6pm-7pm

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Guests toasting glasses of rosé at The Ann Savannah

Tacos & Tequila

Celebrate National Tequila Day with Mediterranean-inspired tacos, specialty tequila cocktails, and live music at Little James.

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A lime margarita with a salted rim and lime slice in the foreground, tacos blurred in the background on a wooden board.

Live Music: Earthtones

Spend your Friday evening with Earthtones, bringing soulful modern R&B, jazz, and neo-soul to Little James from 6–9 PM.

July 18, 2026 6pm-9pm

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Three friends lying on pine needles in a circle, smiling and laughing outdoors in autumn.