After arrival, drop bags at your hotel and ease into Singapore with a leisurely breakfast at Tiong Bahru Bakery (Raffles City) before strolling the waterfront. Explore the historic Fullerton Hotel façade and cross the iconic Helix Bridge to enjoy panoramic views of the skyline, then pop into Esplanade - Theatres on the Bay for a quick photo stop and boutique cafes before a light lunch nearby.
Wander the lush promenades of Gardens by the Bay starting with the cooled wonder of the Flower Dome and the towering, futuristic Supertree Grove, then linger over innovative floral displays at the Cloud Forest conservatory. After botanical bliss, take a relaxed bumboat ride from Clarke Quay upriver to enjoy riverside shophouse views, then sip a refreshing mocktail on the terrace of The Fullerton Bay Hotel as the skyline transitions toward evening.
As twilight falls, head to Marina Bay Sands SkyPark for golden-hour views and a panoramic toast over the city, then descend to wander the illuminated waterfront promenade toward Merlion Park for iconic photos with the statue against the sparkling skyline. Afterward, enjoy upscale casual dining and cocktails at Cé La Vi's terrace-or for something more intimate, reserve a table at Lavo Italian Restaurant & Rooftop Bar-before capping the night with a leisurely riverside stroll past the lit-up facades of The Fullerton Hotel Singapore and a gelato stop at a nearby café.
Start the day with a fragrant breakfast at Pollen in the Flower Dome's neighboring Flower Field Hall before exploring the serene themed gardens like the Heritage Gardens and the reflective pools at Dragonfly & Kingfisher Lakes. Continue with a hands-on experience at the Ginger Garden and a breezy bike ride from the Gardens by the Bay Visitor Centre, then hop a short taxi to Dempsey Hill for boutique shopping and a coffee break at PS.Cafe Dempsey to set a relaxed tone for an afternoon of Orchard Road retail therapy.
After a leisurely morning, take a short taxi to Orchard Road and dive into stylish retail therapy starting at ION Orchard for luxury labels and its rooftop viewpoint, then hop over to Tangs for Singaporean designer finds and unique souvenirs. Pause for a late-afternoon pick-me-up at the whimsical Wild Honey (Orchard) or the peaceful courtyard café at [email protected] before discovering offbeat boutiques and local beauty brands inside Ngee Ann City and the indie concept stores along Scotts Road, finishing with a sunset cocktail at the breezy terrace of The Heeren's rooftop bar to transition into evening plans back toward Marina Bay.
As night falls, head to Clarke Quay for lively riverside dining-reserve a table at Riverside Point or try modern Asian tapas at Jumbo Seafood (Clarke Quay) while watching bumboats glide by. After dinner, stroll to The Live Turtle and Tortoise Museum for a quirky late-evening stop, then finish with cocktails and skyline views at Loof, a rooftop bar with playful vibes and inventive drinks, before catching a short taxi back to your hotel for a relaxed nightcap.
Begin with fragrant kopi and kaya toast at Ya Kun Kaya Toast before wandering the colorful lanes of Chinatown Street Market, hunting for vintage trinkets and artisanal snacks; stop at Buddha Tooth Relic Temple to admire its ornate interiors and rooftop view. Continue with a guided heritage walk through Ann Siang Hill and Telok Ayer, popping into independent galleries and boutique cafes like The Summerhouse's bakery pop-up for a mid-morning pastry and to soak up the neighborhood's blend of old shophouse charm and contemporary art.
After your heritage stroll, wander into Little India's Tekka Centre to sample vibrant street foods like masala dosa and teh tarik at the hawker stalls, then browse colorful textiles and spice shops along Serangoon Road for sarees and henna supplies. Continue to Kampong Glam to explore boutique stores on Haji Lane, sip specialty kopi at a hidden café such as The Sultan Café, and visit the striking Sultan Mosque exterior before an early evening perfume- and batik-shopping session at artisan shops around Arab Street.
As twilight settles, wander into the atmospheric shophouse-lined streets of Ann Siang Hill's dining enclave for small plates at Esquina or modern Peranakan creations at Candlenut Annex, then sip handcrafted cocktails at the intimate speakeasy Operation Dagger tucked down an alley. For a relaxed finish, stroll to the nearby Singapore River Promenade for riverside views and stop at Chijmes to admire the restored chapel and enjoy live music with dessert or a nightcap on the courtyard terrace.
Kick off the day with a sunrise yoga session on Tanjong Beach followed by fresh tropical smoothies at the laid-back Coastes beachfront café, then rent stand-up paddleboards from SupaBoard for a gentle paddle along Sentosa's calm shoreline. After water time, stroll to the nearby Fort Siloso Skywalk for panoramic views and a quick history stop at the coastal fortress exhibits before riding the scenic Sentosa Express or a short cable car hop to continue your island adventures.
Stroll from the morning's calm shore to the lively heart of Sentosa with a beachside lunch at Tanjong Beach Club or the vibrant seafood plates at Coastes' sister venue (beachfront options), then catch the island fun at Adventure Cove Waterpark for thrilling slides, a lazy river float and snorkelling in the Rainbow Reef. After drying off, take the scenic Sentosa Cable Car toward Mount Faber for panoramic photo ops, then descend to explore the nostalgic carnival vibes and street food stalls at Imbiah Lookout, topping the afternoon with a shared local dessert like pandan kaya chendol from a hawker cart before evening plans.
As the sun dips, wander to Siloso Point for sunset cocktails at Tanjong Beach Club's sister bar or the chilled-out terrace of Madame Fan (reserve ahead) while watching beach volleyball games and fire dancers; the vibe is perfect for relaxed group photos and a shared platter. After drinks, head to Wings of Time for an atmospheric night show of light, water and pyrotechnics on the bay, then cap the night with late-night bites and boardwalk stargazing at Quayside Isle (Sentosa Cove) or a cozy dessert at Snack Shack before returning to your hotel.
Ease into the day with a leisurely brunch at The Lokal near the Civic District, savoring Aussie-style dishes and strong coffee before a cultured stroll to the nearby National Gallery Singapore to admire Southeast Asian masterpieces and rooftop views from the gallery café. Continue with a focused museum hop to the contemporary exhibitions at the ArtScience Museum (check rotating exhibits) and a reflective walk through the colonial-era lawn and sculptures around Padang, pausing for photos beside the stately Old Parliament House before lunch.
After a cultured morning, take a leisurely riverside walk toward Clarke Quay Central and hop on a guided heritage cruise from Singapore River Cruises to learn local stories while passing colorful shophouses. Disembark near Asian Civilisations Museum for a late-afternoon tea at the museum café, then browse its galleries focused on regional art before ascending to The Clifford Pier Bar for pre-dinner cocktails with river views as you transition into the evening.
As twilight arrives, wander to The Fullerton Rooftop for sunset aperitifs and sweeping river-and-padang views, then descend to sample inventive small plates at Humble Jon's for a relaxed, flavor-forward dinner. Afterwards, hop across the river to Mr Stork for elevated cocktails with panoramic cityscapes and finish the night with live jazz and late-night bites at the cozy speakeasy Blu Jaz Cafe in nearby Arab Street for a lively end to the day.
Squeeze in one last taste of Singapore with breakfast and souvenir hunting at Tiong Bahru Market & Food Centre, where kopi and freshly steamed kaya buns pair perfectly with a browse of artisan stalls and local snacks to take home. Next, head to Jewel Changi's Canopy Park for a relaxed walk across the HSBC Rain Vortex and final gift-shopping at specialty boutiques like Changi Transit Duty Free and indie shops in Shilla Duty Free, then allow time to check luggage at the terminal lounges before a calm transit to your departure gate.
Head back into the city for a relaxed last-afternoon pit stop at Chinatown Complex Market & Food Centre to grab any final edible souvenirs and a comforting plate of char kway teow or bak kut teh before shopping. Then stroll through Ann Siang Hill's boutique lanes to pick up stylish local jewelry and beauty finds at independent shops, finishing with a restorative tea or iced matcha at Tea Chapter before returning to the airport with plenty of time to spare.
For a relaxed final evening, wander through the atmospheric shophouse-lined Tanjong Pagar district and enjoy a casual seafood feast at Tippling Club's more accessible bar menu or sample hawker-style crudo at Chinatown Food Street's nearby late stalls. After dinner, take a short taxi to Marina Barrage for a peaceful skyline picnic as the city lights come alive-perfect for group photos-and finish with dessert and cocktails at the breezy rooftop bar Level33 for one last panoramic toast before heading to the airport.