Urban Vines & Sky-High Wines: A 2-Day Singapore Itinerary for Wine Lovers

The day opens on Duxton Road, where the light is still soft and the shophouses wear their pastel paint like pressed linen. You slip into Dill, the cool of the interior a relief from the already-thick air, and the smell of coffee and buttered bread mingles with the faint spice drifting in from the street. By late morning, you’re only a few steps away at Praelum Wine Bistro, where the clink of glassware and low conversation turn the quiet lane into a classroom for your palate, each pour a small, precise lesson. Lunch carries you to Keong Saik at Vinflow, where the texture of the wooden bar under your forearms and the hum of an easy playlist make those free-flow wines feel dangerously effortless. Afternoon stretches into the CBD at Artemis Grill & Sky Bar, forty floors up, where the city looks like a circuit board and the breeze feels almost cool against your skin; vines might be thousands of kilometres away, but the wine list reads like a global map. As the sky dims, you’re back on Tras Street at Madame, all moody lighting and velvet tones, where plates and pairings feel as composed as a gallery show. You close the night at Bar A Vin in Raffles Place, the city outside reduced to a soft roar as you sit beneath warm lights, tracing the day’s arc through each glass. Tomorrow, the scene shifts – same city, different tempo, trading CBD glass for Katong pastels and Sentosa sea air.

Morning breaks softer in Katong, the sound of traffic muted under birdsong and the clink of cups in neighborhood cafés. You wake your palate at Holiday Inn Express Singapore Katong’s surrounds, stepping out into East Coast Road where the air smells faintly of pandan, coffee, and exhaust, then wander towards BoundbyWine and the candy-store rows of bottles that feel more like a friend’s curated shelf than a faceless retailer. By late morning, you’re deeper into this side of town at Wine Mouth on Joo Chiat Road, running your fingers along cool glass and tracing labels from regions you’ve never heard pronounced out loud. Lunch pulls you back toward the river at Restaurant Ibid, where the space feels calm and almost monastic, an ideal backdrop for wines that thread through modern Chinese-inflected plates. Afternoon drifts into the green hush of Gardens by the Bay, Cloud Forest and Flower Dome offering a kind of tropical terroir tour under glass – orchids, cool mist, and the distant chatter of families echoing off steel and glass. As the light fades, you cross to Sentosa, where Fiamma and Bob’s Bar share the same hillside: dinner in a room scented with wood-fired Italian warmth, then a final glass at a bar that smells of sea air and cigar smoke, the night closing with the rustle of palm fronds instead of city horns.