Skyline Sips & Urban Vines: A 6-Day Wine, Rooftop Bar & Urban Vineyard Trail in Singapore

The day begins in cool, manufactured cloud. You step into Cloud Forest and the air hits you — mist on your skin, the roar of the indoor waterfall echoing off glass, orchids beading with droplets like they’ve just exhaled. Morning here feels almost alpine despite the equatorial heat outside, a quiet reset before the city’s sharp edges appear. By lunchtime, you’re in a minimalist shophouse on North Canal Road, Restaurant Ibid’s pale walls and clean lines framing plates that play with Chinese heritage and natural wine in equal measure. The afternoon slows further at Praelum Wine Bistro on Duxton Hill, where the soundscape shifts to low conversation, corks easing out of bottles, and cutlery on small plates. Wood, brick, and the faint smell of grilled squid make it feel like a European side street, except the humidity outside reminds you you’re in Singapore. As the light softens, you ride an elevator up to VUE, where floor-to-ceiling windows turn the skyline into theatre and the tablecloths feel almost too crisp to touch. Later, Deviate Wine Bar in Dempsey wraps the night in darker tones: soft jazz, cool concrete floors, and a sense that you’re already moving off the obvious path. Tomorrow, the city tightens its focus as you sink into the shophouse maze of Club Street and Keong Saik.

The day opens slowly in Keong Saik, where the shophouses are still yawning awake and the air smells of espresso and warm bread. Acqua e Farina’s tiled floor is cool underfoot, and the morning light slides across plates of eggs and Italian pastries in a way that makes you linger over coffee. By late morning you drift toward Ann Siang Hill, shophouse shutters thrown open, the sound of delivery trucks and the distant hiss of woks in back alleys. Lunch at THE COUP Bar on Ann Siang Hill blurs the line between bar and kitchen — plates with just enough edge to match their natural-leaning wines, set against an eclectic interior that feels like someone’s stylish living room. The afternoon belongs to The Otherside on Erskine Road, where craft beer fridges hum softly and the rooftop terrace catches whatever breeze there is. As the sun sinks, you climb to 23 Ann Siang, where trivia nights and off-duty creatives turn the bar into a kind of clubhouse. Later, Madame on Tras Street wraps the night in velvet tones and Parisian-boudoir lighting, a last drink in a room that feels like a secret. Tomorrow, the focus sharpens on Keong Saik’s wine haunts and a tasting-menu crescendo.

The city feels a touch slower this morning, so you lean into it. My Awesome Cafe on Telok Ayer Street occupies a former Chinese medical hall, and the bones of the space show: high ceilings, old signage, and the clatter of cutlery against mismatched plates. The smell of coffee, toasted bread, and something slightly herbal hangs in the air as sunlight slants through tall windows. It’s an easy place to sit longer than intended, watching office workers filter in and out. Lunch shifts into high gear at Restaurant Born, where the room is all polished concrete, curated art, and the soft thrum of a serious kitchen. Plates are intricate without feeling fussy, each course a small story that pairs beautifully with a considered wine list. Afternoon at Vinflow Wine Bar & Bistro keeps you in a wine haze but in a looser way — free-flow machines humming softly, friends debating favorites over snacks. As dusk settles on Duxton Hill, SG Taps introduces a different kind of pour, Japanese-Singaporean plates under warm lighting and the soft hiss of beer taps. Later, Side Door on Neil Road pulls you into a hybrid space of cafe-turned-bar, where cocktails and small bites carry the night. Tomorrow, you step away from the inner core and let Champagne and Marina Bay’s cultural side take over.

Morning light bounces off the glass skin of Marina Bay Sands as you ride the elevator up to the Roof Garden. Up here, the city feels strangely quiet: just the soft whirr of pool filters, the rustle of plants in the breeze, and the distant hum of traffic far below. The garden paths are smooth underfoot, and the air smells faintly chlorinated and green, like a sky-high park. It’s a calm, elevated way to reset your sense of scale before you head back to ground level. Lunch pulls you toward the Esplanade, where BayBay — Yunnan Cuisine Bistro — sits with its own rhythm, plates scented with chili, herbs, and the deep, earthy notes of Yunnan cooking. Afternoon is for Convivial Champagne Bar on North Canal Road, where the owner talks about grower Champagne with the fervor of a true believer and the air feels almost electrically charged with tiny bubbles. As the sky darkens, The BOILER @ Esplanade turns things louder: seafood, spice, and bar chatter bouncing off the waterfront mall’s curves. You finish on Circular Road at Anthology, where cocktails and spirits take center stage in a narrow, atmospheric bar. Tomorrow, you trade glass towers for Joo Chiat’s pastel facades and rice wine stories.

Today the city shifts from glass towers to human scale. Morning begins at Holiday Inn Express Singapore Katong’s surrounds — think bright, efficient, and steps from local kopitiams if you’re staying there — but your real focus is the East Coast corridor. By late morning you’re in Joo Chiat, which travel writers keep circling back to as one of Singapore’s most characterful neighborhoods: pastel shophouses, Peranakan tiles underfoot, and the sound of scooters and schoolkids instead of office traffic. Ye Traditions Rice Wine in Ang Mo Kio pulls you deeper into local drinking culture, where handcrafted rice wines feel more like family heirlooms than products. The space smells faintly sweet and ferment-y, with bottles lined like a tiny gallery. Afternoon leads you to BoundbyWine in Joo Chiat and then Wine Mouth, both warehouse-style and shophouse bottle shops where shelves of labels tell a different story of “terroir” — global but curated for this humid island. As the light fades, The Sundowner Nature Experience Centre on East Coast Road takes you up to a rooftop micro-farm, where the air smells of soil and herbs and the city hums below. Salud on Keong Saik pulls you back into the inner core later, a gin-forward bar with the kind of aesthetic that makes you forget what time it is. Tomorrow, your final day loops back to the city’s wine education side and a last sweep through Gardens by the Bay.

Your final day leans into education and spectacle. Morning at Fine Wines Pte Ltd on Lavender Street feels like sneaking into the back-of-house of Singapore’s wine world: warehouse corridors, cool air, and racks of bottles that read like a roll call of serious producers. The space smells of cardboard, wood pallets, and the faintest hint of cork — a working cellar where classes and tastings happen among the stock. It’s a fitting nod to the infrastructure that makes all those bar lists possible. Lunch at Club Street Laundry Modern Australian Eatery pulls you back into the social front-of-house, where the clatter of cutlery and the smell of charred edges and espresso mingle in a bright, modern room. Afternoon at ewineasia’s warehouse shop in Pasir Panjang extends the cellar theme, another chance to run your fingers over labels and talk to people who live and breathe distribution. As the sun softens, Gardens by the Bay and Supertree Grove take over: metallic trunks lit from within, paths that smell of damp earth and tropical blooms, and the sound of the Garden Rhapsody light-and-sound show echoing through the air. You close the loop at Last Word on Purvis Street, a classic bar where the lighting is low, the cocktails are precise, and the city outside finally feels like it’s exhaling with you. You leave with the taste of a well-made drink and the memory of a skyline that now feels familiar.