The Bootlegger Savannah Speakeasy

The Bootlegger Savannah Speakeasy captures the mystique and charm of a bygone era, blending a rich Prohibition-style atmosphere with a sophisticated culinary and cocktail experience along Savannah’s picturesque River Street. This bar and restaurant isn’t just a place to eat and drink—it’s a journey into the Jazz Age, made all the more thrilling by the warm, inviting spirit of its staff and the whispers of history their stories evoke.

Step inside The Bootlegger, and you’re instantly transported to a dimly lit, vintage speakeasy, where crackling jazz melodies and the flicker of old black-and-white TVs create an immersive ambiance that feels both intimate and alive with secrets. The lighting is perfectly moody, and the décor is thoughtfully retro, allowing guests to feel like they’ve slipped beneath the radar into a hidden haven of flavor and story.

The culinary offerings here are a highlight worth savoring. While The Bootlegger doesn’t boast an extensive dinner menu, its curated selection of small plates—lovingly referred to as “Bootleg Bites”—are packed with bold flavors and crafted to satisfy. The Capone’s Crab Cakes arrive golden, tender, and generously packed with fresh crabmeat, perfectly accented by a zesty remoulade and a squeeze of lemon that awakens the palate. For a taste of coastal luxury, the Oysters on the Half Shell deliver pristine briny freshness, chilled to perfection and complemented by house cocktail sauce and a classic mignonette. For something richer, the Oysters Rockefeller are a decadent choice, baked with creamy spinach, garlic, and a crispy Parmesan topping that offers a comforting yet elegant bite.

For those seeking a little crunch and southern flair, the Speakeasy Fried Green Tomatoes offer a crisp, tangy sensation that beautifully contrasts with the smoky and savory small plates. The flavor-packed Mob Boss Meatballs and flatbreads like the Scampi Street Flatbread, adorned with garlic shrimp and melted mozzarella, or the timeless Garden District Margherita, layered with ripe tomatoes and fresh basil, round out a menu designed to share, savor, and enjoy with friends.

When it comes to cocktails, The Bootlegger truly shines. This is a haven for enthusiasts of expertly crafted drinks born from the Prohibition era and beyond. Signature cocktails like the Sidecar, Roosevelt’s Smoked Old Fashioned, and the intriguing 1933 Prohibition Punch are all meticulously balanced and beautifully presented. Customers often rave about the bartenders—nicknamed Mickey, Bugsy, and Lucky—who are as much historians and entertainers as they are mixologists, offering stories and insights that enrich every sip. The classic Bloody Mary and a perfectly made Manhattan round out a lineup that honors tradition while embracing craft creativity.

Finish your evening with a nod to the sweet side of the Jazz Age. The Pineapple Upside Down Cake is a nostalgic showstopper, boasting caramelized pineapple atop moist vanilla cake that truly tastes like a delicious slice of history. Or, if you’re craving something richer, the Chocolate Temptation Cake delivers decadent layers of chocolate indulgence, while the warm Georgia Peach Cobbler, served with vanilla bean ice cream, offers a comforting, sweet southern finale.

What truly sets The Bootlegger Savannah Speakeasy apart is its soul. The genuine connection between staff and guests creates an atmosphere that feels like you’ve been let in on a secret, a place where the stories flow as richly as the bourbon. Guests consistently praise the welcoming bartenders, the uniquely curated music, and the captivating vintage ambiance. Whether you’re unwinding solo or sharing a special night with friends or loved ones, The Bootlegger delivers a sensory experience that resonates emotionally—where every sip, bite, and whispered story invites you deeper into Savannah’s spirited past.

If you’re searching for an authentic and intimate taste of Savannah’s historic charm, paired with cocktails and small plates that delight every sense, The Bootlegger Savannah Speakeasy is a must-visit destination that feels like your own secret hideaway. Just remember to ask the bartenders for their signature bites and the legendary Gangster’s Paradise cocktail for an unforgettable experience.