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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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.

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.

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

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.