Hipster Prague in Winter: 3 Days of Speakeasies, Craft Cocktails & Late-Night Vinyl Bars

The day starts with stone and silence. Old Town Square is still shaking off sleep, the Astronomical Clock ticking over while a few delivery vans hiss across wet cobbles. You stand under the dark ribs of the Old Town Bridge Tower, the Vltava below moving slow and metallic, and it feels like the city’s medieval machinery is quietly spinning up for you alone. By late morning you’re in a different Prague: neon halos and optical illusions at Signal Space, a reminder that this is a capital as obsessed with light installations as with Baroque facades. Lunch is warm and precise at Czech Slovak Restaurant, where steam rises from Kulajda soup and roast duck, and the clink of cutlery mixes with soft Czech chatter. The afternoon drifts into POP ART STUDIO PRAGUE—Warhol colors, sharp lines, the slick feel of gallery floors under your boots—before you cross the river’s invisible border into Vinohrady. Dinner is a slow, candlelit affair at Restaurant Mlýnec with jazz threading through the room, then the night blooms properly in Savage Bar, where cocktails arrive smoking, glowing, or otherwise showing off. You head back through the cold with a faint sugar burn on your lips and the sense that tomorrow you’ll push further out, into the neighborhoods locals actually argue about over beers.

You wake to a quieter Prague, last night’s jazz replaced by the soft scrape of snowplows and the rattle of trams heading toward Žižkov. Morning belongs to HIDDEN gallery, where the walls sweat with contemporary work and the clink of Bráník bottles reminds you art here is meant to be lived with, not whispered around. From there, the day loosens: a short hop to Karlín, the neighborhood every local guide now frames as “the one to watch”—all converted factories, design offices, and wine bars with more MacBooks than menus at lunchtime. Lunch at WineList feels slightly decadent: the hiss of automatic dispensers, the snap of crisp bread, the velvety slide of Moravian reds in your glass before it’s even 2pm. The afternoon stretches along the river at Revír Karlín, where office workers and creatives blend over long drinks, the Vltava moving slow and grey just beyond the windows. By evening you’re back on the Old Town side, ducking into Beyond The Bar, where the line between cocktail program and performance art blurs under strobes and bass. Tomorrow will bring high walls and higher altars up at Prague Castle, but tonight is all about that slightly feral, mid‑week city energy that never makes it into tourist brochures.

This morning is all about altitude and quiet. Vyšehrad rises above the river, its thick walls rimed with frost, the city’s spires puncturing the low cloud line in the distance. As you walk the ramparts, boots crunching on gravel, Prague feels less like a fairy tale and more like a fortress that learned how to party. By late morning you’re trading stone for stained glass at St. Vitus Cathedral and the wider Prague Castle complex, where footsteps echo off centuries of power and incense still hangs in the air around side chapels. Lunch takes you back down into the city’s everyday rhythm at The Street Burgers, all sizzling fat, soft buns, and the low hiss of a busy grill. The afternoon slows at DOX Centre for Contemporary Art in Holešovice, a district the neighborhood guides always single out as Prague’s hip, warehouse‑turned‑gallery quarter; here, concrete, glass, and a full‑scale airship on the roof replace Gothic arches. After dark, you slide into Vinohrady proper for a last circuit: Bar GINGER’s intimate glow, Americká 32’s game‑night energy, and a final late‑night glass at BOHO wine & bar. It’s the kind of night that leaves you with ink‑black tram windows, record‑store playlists in your head, and the feeling that you’ve only just started to decode this city.