Skyline Strolls, Street Food, and Sophistication

Singapore is one of those places that seems to live slightly in the future—gleaming towers, pristine streets, and an airport so luxurious it’s practically a destination on its own. But behind the modern gloss lies a fascinating history, a fiercely multicultural society, and a spirit of precision and pride that sets it apart from anywhere else in Southeast Asia.

When you ask any local what the best things are to do in their town, you’ll mostly get a list of restaurants and cocktail bars. And for good reason! The city is incredibly diverse and known for its dazzling array of restaurants… including no fewer than 51 Michelin starred establishments. This puts it in the top tier of great restaurants per capita (7th in the world). Interestingly, it even has the world’s cheapest Michelin star restaurants. Included on the prestigious list are at least 2 street food stalls.

Originally a British trading post founded in 1819 by Sir Stamford Raffles, Singapore quickly grew into a thriving colonial outpost and later a major port city. It gained independence in 1965 and has since transformed itself into a global financial powerhouse. The city-state is governed as a parliamentary republic with a strong central government. Singapore is known for its low crime, high efficiency, and remarkable ability to blend order with vibrant culture.

I’ve been to Singapore more than a half dozen times for work. And each time this small metropolis reveals something new. When I think I’ve seen everything there is to see, I find something new and totally amazing.

Here’s an itinerary for you to spend three incredible days soaking in the city’s contrast of nature and neon, elegance and street food, tradition and innovation. Here’s what you should know and do.

A Food Lover’s Paradise

First off, you should know that each night in Singapore is a feast. The city’s culinary scene is one of the best in the world, balancing high-end innovation with street-level authenticity. There are several high density restaurant areas to explore, including Haji Lane and Boat Quay.

You can be indulgent and go for a multi-course meal at Odette. This is a modern French restaurant that’s consistently ranked among Asia’s best. Save this for a special night.

And you should try one of the Hawker centers like the Newton Food Centre, the most popular, or Old Airport Road, where locals go. Highlight here is definitely tearing into Singapore’s famous chili crab. But you can also get other amazing local specialties such as Prata, indian rojak, chinese rojak, nasi lemak, mee goreng, epok-epok, chendol, asam pedas, mee soto, or chee cheong fun.

And then, of course, you must try some carrot cake (chai tow kway), the National dish of Singapore —which is neither made of carrots nor a cake in the traditional sense. It’s a savory dish made from fried radish cake, scrambled with eggs, garlic, and preserved radish. It comes in a “black” version (with sweet soy sauce) and a “white” version (without), and it’s a national obsession for a reason.

Day 1: The Marina Bay Waterfront and Gardens by the Bay

First head to the city’s most iconic district: Marina Bay. Start by exploring the Esplanade, and then head over to the waterfront promenade. Along the way you’ll get a sense of the city’s careful urban planning. Everything has its place. The skyline is sleek, yet softened by water and greenery.

Walk to Gardens by the Bay, a futuristic green space that looks like something from a science fiction novel. The Supertree Grove is breathtaking—towering vertical gardens that light up with music at night. This truly is a magical sight. But the real highlight is the OCBC Skyway. This is a suspended walkway high among the trees offering stunning views.

By mid-day, when the weather starts warming up, head inside the Flower Dome and Cloud Forest. Here you can explore climate-controlled biomes filled with exotic plants, waterfalls, and mist-covered paths. It is tranquil and surreal—nature reimagined through architecture and innovation.

That evening, catch the sun set at Marina Bay Sands. Head up to the top for the views (it is about $40 per person to go to the top deck). Then you can eat at Spago by Wolfgang Puck, perched on the 57th floor with views that seem to stretch forever.

Day 2: Sentosa Island Adventures and Sunset Cocktails

Day two: head south to Sentosa Island, Singapore’s resort playground. Ride the Sentosa Express air tram across the water, gliding above ships in the harbor and rows of palm trees below. It’s a short ride, but it immediately makes the city feel like a vacation.

Once on the island, there are a number of activities, including Universal Studios amusement park, the S.E.A. Aquarium and the Adventure Cove Waterpark. For something more unique and local, head for the Skyline Luge—a gravity-powered thrill ride down winding jungle tracks. Race down the hill in you personal go-cart, and then you can take the chairlift back up for another go. It’s just the right amount of adrenaline.

You can take a cable car from Sentosa up to the peak of Mount Faber, and from there hike about 10 minutes to the scenic Henderson Waves Pedestrian Bridge, high above the city.

At the bottom you can wander along the beaches and boardwalks. My favorite is the Bikini Bar, a breezy beachfront spot with cold beer and great music. With your feet in the sand and a cocktail in hand, the city feels a world away.

Have dinner that night at the award-winning Burnt Ends, a modern grill known for its bold flavors and Singaporean edge. Every bite is smoky, rich, and unforgettable.

Or head to Boat Quay for cocktails and get a more relaxed meal along the edge of the Singapore River. There are many restaurants and lounges here or further down at Clark Quay.

Day 3: Botanic Gardens and a Taste of Tradition

If you are ready for a slower pace and you love gardens like I do, head to the Singapore Botanic Gardens, a UNESCO World Heritage site and one of the oldest (and best) gardens of its kind in the world. The lush grounds are expansive, filled with winding paths, serene lakes, and a stunning National Orchid Garden. You can wander for hours, breathing in the scent of frangipani and listening to birdsong, marveling at how quiet it can be in the middle of a metropolis.

In the afternoon, make your pilgrimage to Raffles Hotel, the colonial-era grand dame of Singaporean hospitality. Sitting in the Long Bar with ceiling fans spinning lazily above you, you can order two Singapore Slings—the famously fruity gin-based cocktail that was invented here over a century ago. Sure, this may be totally touristy, but you wanted to see it, didn’t you? Check out the Sling Shaker; a cocktail shaking machine built specifically for the Raffles.

After your lunch and afternoon cocktail, head over to Haw Par Villa. This is one of Singapore’s most unusual and fascinating attractions—a theme park unlike any other. Built in the 1930s by the creators of Tiger Balm, this sprawling garden is filled with more than a thousand colorful statues and dioramas that bring Chinese folklore, mythology, and moral lessons vividly to life. The most famous (and perhaps most chilling) section is the “Ten Courts of Hell,” which graphically depicts traditional beliefs about the afterlife, but there are also whimsical scenes of legendary heroes, animals, and folk tales scattered throughout the park. It’s quirky, educational, and a little surreal all at once, making it a must-visit for travelers who want to experience a truly unique slice of Singaporean culture and history.

Where to Shop

Singapore also happens to be one of Asia’s best shopping destinations. For high fashion and luxury, Orchard Road is the place to go—lined with gleaming malls and flagship stores. For something a little more local, we love wandering the boutiques of Haji Lane, a hip street in the Kampong Glam district full of indie fashion, design shops, and cool murals.

And if you’re looking for deals, the Bugis Street Market is very hip and packed with affordable clothes, souvenirs, and a few unexpected treasures. A few other good unique/boutique shopping areas include Ann Siang Hill and Tiong Bahru.

The Final Stop: Changi Airport – A Destination in Itself

It’s not often that an airport becomes one of the highlights of a trip—but Changi Airport is no ordinary airport. Widely regarded as the best in the world, Changi feels more like a luxury resort or futuristic garden complex than a transit hub. Give yourself a few hours and arrive early to take full advantage.

The centerpiece, of course, is Jewel Changi—a multi-level shopping, dining, and entertainment complex that wraps around the Rain Vortex, the world’s tallest indoor waterfall. You’ll stand beneath it in awe, watching the water cascade from a circular oculus in the glass ceiling seven stories above. It is hypnotic and strangely calming, especially when the light show begins. As day turns to night, the waterfall comes alive with shifting colors, music, and mist—a last burst of magic before boarding your flight.

Just as memorable is the food and cocktail scene surrounding the vortex. Grab your last meal in Singapore at any one of dozens of restaurants – try Tonkatsu by Ma Maison. For drinks, there are biergardens and sleek cocktail lounges with direct views of the Rain Vortex. We like Cloud9 Piazza where you can linger over beautifully crafted cocktails as the lights shimmer behind the falling water. There is a peaceful, celebratory feel to it—like the city is giving us a soft, stylish sendoff.

Even saying goodbye in Singapore is an experience. At Changi, the journey doesn’t end until you’re airborne.

Final Thoughts

Singapore is often described as a “gateway” city or a stopover. And indeed it is the layover you’ll need to make to get to most places in southeast Asia. But maybe Singapore should be a destination in its own right. It is vibrant and expanding constantly. It’s a place where cultures intersect with grace, where the future meets tradition, and where every meal is a memory. Whether you’re admiring orchids in a colonial garden or flying down a luge track by the sea, Singapore finds a way to surprise you—in the most delicious, refined, and quietly thrilling ways.

If it’s not already on your list, move it up. Singapore isn’t just a clean, efficient city. It’s a world all its own.