A five to six-hour flight, direct connections from 16 Indian metros, and a city designed for efficiency make it one of the rare destinations where a short trip feels complete rather than compromised. Here, you can move from temples to cocktails, forests to galleries, without ever feeling rushed. Compact in scale but generous in variety, Singapore continually offers new ways to discover the city beyond the expected.
Layer in a year-round calendar, from Singapore Art Week to the Singapore Food Festival and the Singapore Grand Prix, festive Deepavali streets and a spectacularly choreographed year-end fireworks display over Marina Bay, and the decision makes itself.
If a long weekend is all you’ve got, this is how to do Singapore well.
Day 1: Kampong Gelam to Chinatown
Changi Airport to city centre: 25–30 minutes by taxi or MRT
Check into a centrally located hotel. The Mondrian Singapore Duxton brings art-forward energy, Ann Siang House offers boutique charm in a restored heritage building in Chinatown, while The Capitol Kempinski keeps things classy in the civic district.
Start in Kampong Gelam
Travel time: 10–15 minutes from most central hotels
One of Singapore’s oldest neighbourhoods, Kampong Gelam blends layered history with a quietly contemporary energy. Visit Sultan Mosque, the city’s oldest mosque with stunning Indo-Islamic architecture, crowned with a glittering golden dome. Then duck into Aliwal Arts Centre for contemporary exhibitions, followed by a sensory stop at Jamal Kazura Aromatics for a custom-blended scent, an unexpectedly personal souvenir. Walk Arab Street for textiles, from the encyclopaedic shelves at Gim Joo Textile Company to the Malay prints at Basharahil Bros Batik. Lunch is at Zam Zam Restaurant to experience the neighbourhood’s Indo-Malay roots. Get your caffeine fix at Twenty Grammes before you venture further.
Head to Chinatown
Travel time: 15 minutes by taxi or MRT
As evening approaches, shift gears to Chinatown, where temples and heritage shophouses sit alongside vibrant street food stalls and low-key bars. Walk Bukit Pasoh Road and Club Street slowly, noticing former clan houses and restored façades. Step into the Buddha Tooth Relic Temple for a moment of calm and rooftop views.
For dinner, keep it casual at one of the hawker stalls at Maxwell Food Centre (first-timers can try Tian Tian's Bourdain-approved Hainanese Chicken Rice), or up the ante with a reservation at Restaurant Fiz, awarded a Michelin Green Star for sustainable fine dining in Singapore, where Malay staples get a fine-dine makeover. End with a nightcap at the four-seater Hup San Social Club, where a savoury cocktail inspired by Korean chilled cucumber soup has become something of a cult favourite, or head to the high-energy speakeasy Employees Only for drinks and feels in equal measure.
Day 2: Design Blocks, Tree Canopies and the East Coast
Begin in Tiong Bahru
Travel time: 15 minutes from city centre
Admire the Art Deco blocks that make Tiong Bahru one of Singapore’s most characterful neighbourhoods. Built in the 1930s as the city’s first public housing estate, it has since evolved into a quietly cool area of cafés, bookshops and design stores. Wander through the Tiong Bahru Market to watch daily Singapore unfold, from aunties shopping for vegetables to long queues forming at cult hawker stalls.
Then head to Gillman Barracks, about 20 minutes away, for contemporary gallery-hopping inside a former British military enclave. Don’t miss Richard Koh Fine Art, one of Singapore's most respected galleries, or Sundaram Tagore Gallery for museum-grade exhibitions that regularly feature major international and Asian artists.
Escape the heat at the Southern Ridges
Travel time: 15 minutes
When the city heat starts to press in, swap concrete for canopy at the Southern Ridges. The Henderson Waves walk is short, elevated and cooling, with stunning treetop views that more than justify the detour.
Evening in Katong–Joo Chiat
Travel time: 25 minutes
Catch golden hour on Koon Seng Road, where highly Instagrammable Peranakan shophouses glow like a film set, then head into Katong Shopping Centre for a Bazi (eight-character divination) destiny reading at Ghostbusters, one of Singapore’s most quirky cultural detours. Dinner at Baba Chews delivers updated Peranakan and international flavours—think Chilli Crab Cake with Mantou Chips, slow-braised Beef Cheek Rendang, and Nikkei inspired Grilled Assam Halibut Risotto. End with a Smoked Sazerac or a Negroni at 60ml located within restaurant Asador, or Spanish-inspired cocktails at the Gaudí-themed hidden bar at Carlitos.
Day 3: Creative Districts and a Waterfront Goodbye
Morning at New Bahru
Travel time: 10–15 minutes from city centre
Singapore’s creative scene comes together under one roof at New Bahru, a former girls’ school reimagined as a vibrant lifestyle hub. Browse homegrown labels from Sea Apple Create Store’s thoughtfully designed kidswear to Peiper’s floral paper sculptures and Studio Yono’s eclectic art and home décor, founded by a former journalist. When hunger calls, head to The Coconut Club for a proper nasi lemak: fragrant coconut rice, crispy chicken and fiery sambal that hits the spot after a morning well spent.
Walk through Telok Ayer
Travel time: 15 minutes
Visit Thian Hock Keng Temple, then stroll Amoy Street where street art, restored shophouses and office towers together speak eloquently of Singapore’s rich historical tapestry. Cut uphill to Ann Siang Hill Park. After a coffee at Maxi Coffee Bar on Club Street, saunter around the neighborhood, admiring its larger-than-life colourful murals and pop in to Arkive Store for curated vintage buys.
Sunset at CHIJMES and then the Waterfront
Travel time: 10–15 minutes
Wander through CHIJMES, a historic convent-turned-lifestyle district and home to two National Monuments (CHIJMES Hall and Caldwell House). Stop for an iced matcha latte at the glass-walled biophilic Glasshouse or a handcrafted gelato at Petals & Peak before heading to the roof terrace at Esplanade – Theatres on the Bay’s for sweeping skyline views. Walk the Helix Bridge as the lotus-shaped ArtScience Museum lights up. Round off the evening with dinner and drinks at Spago Bar & Lounge or Le Noir at Marina Bay Sands.
Three days, full experiences and memories that linger. Singapore doesn’t ask for more time, only a willingness to wander off-script.
