Singapore—a city where towering skyscrapers meet lush green spaces, where hawker stalls serve world-class food, and where every street corner tells a story. It’s a place that feels both futuristic and deeply rooted in history, all at once. And the best part? You don’t need a huge budget to explore it like a pro.
This is a guide for the DIY traveler—the one who loves to wander, discover hidden gems, and experience a city beyond the tourist brochures. And fall is the perfect time to do it.
Welcome to the Lion City: A Perfect Fall Destination
October is one of the best months to visit Singapore. The summer heat has eased up (slightly), the crowds have thinned, and there’s an energy in the air that makes you want to explore. With a well-rated, affordable hotel near downtown, you’re already set up for success. Now, it’s time to hit the streets and dive into the heart of this incredible city.
Wandering Through Singapore’s Must-See Attractions
If there’s one thing about Singapore—it’s that this city knows how to impress.
Gardens by the Bay is a no-brainer. Those towering SuperTrees? Even more mesmerizing in person. Walk the OCBC Skyway at sunset for an unforgettable view, then stick around for the free Garden Rhapsody light show.
Just a short stroll away is Marina Bay Sands. Whether you splurge on a rooftop cocktail or just admire the infinity pool from afar, the view from the observation deck is breathtaking.
For a taste of old Singapore, take a wander through Chinatown, Kampong Glam, and Little India. These neighborhoods burst with character—colorful shophouses, temples, markets, and some of the best street food in the world. In Chinatown, visit the Buddha Tooth Relic Temple, then lose yourself in the alleyways filled with quirky shops and cafés.
And let’s not forget Sentosa Island. If you’re feeling adventurous, take the cable car for a scenic ride across the island, visit Siloso Beach, or check out the S.E.A. Aquarium—one of the largest in the world.
Eating Like a Local – A Wanderer’s Dream
Singaporeans take their food very seriously, and once you try it, you’ll understand why.
The best part? Some of the city’s most famous dishes cost less than $10.
- Maxwell Food Centre – Home to the legendary Tian Tian Hainanese Chicken Rice (Anthony Bourdain swore by it).
- Lau Pa Sat – A stunning 19th-century hawker center where you can feast on satay skewers fresh off the grill.
- Tiong Bahru Market – A local favorite with top-notch laksa, roti prata, and kopi (Singaporean coffee).
- Chomp Chomp Food Centre – If you want to dive deep into Singapore’s hawker culture, this is the place. Try the Hokkien Mee and sugarcane juice.
Want something fancier? Head to Newton Food Centre, famous from Crazy Rich Asians, or explore the vibrant restaurants along Clarke Quay.
Singapore After Dark – The Nightlife & Hidden Bars
When the sun goes down, Singapore turns into an entirely different city. The skyline lights up, the streets come alive, and the bars are some of the coolest in the world.
- Atlas Bar – A stunning 1920s-style bar with one of the largest gin collections on the planet.
- Manhattan – Consistently ranked among the world’s best bars, this place serves next-level cocktails.
- Clarke Quay – If you want buzzing nightlife, live music, and riverfront drinks, this is the spot.
- Ce La Vi – Perched on top of Marina Bay Sands, this rooftop bar gives you insane views over the city.
And if you’re feeling adventurous? Try finding one of Singapore’s hidden speakeasies, like Operation Dagger or 28 HongKong Street. They’re tucked away in unmarked buildings, but trust me—it’s worth the hunt.
The Joy of Renting a Car & Exploring Beyond the Cit
Most people don’t think about renting a car in Singapore, but if you’re a true wanderer, it’s an absolute game-changer.
Why? Because once you get out of the city, Singapore has some seriously underrated spots:
- Pulau Ubin – A short ferry ride from the mainland, this island is a throwback to old Singapore. Rent a bike and explore rustic trails, mangroves, and kampong (village) houses.
- Changi Beach – A quiet stretch of sand where you can watch planes land while sipping a fresh coconut.
- Southern Ridges – A stunning hiking route that takes you through lush greenery, futuristic bridges, and breathtaking skyline views.
- Johor Bahru (Malaysia) – If you’re feeling adventurous, drive across the border into Malaysia! JB is just a short trip away, and the street food here? Unbelievable.
Having a car gives you total freedom—no waiting for buses, no crowded MRT, just you and the open road (well, as open as Singaporean roads get).
The Budget – How Much Will You Spend Per Day?
Singapore has a reputation for being pricey, but a wanderer on a budget can get by comfortably for about CAD $60–$80 per day (excluding flight & hotel).
Here’s a rough breakdown:
- Food: $15–$25 (hawker food is super affordable)
- Transport: $5–$10 (MRT and buses are cheap, taxis are pricier)
- Attractions: $20–$30 (Gardens by the Bay, museums, etc.)
- Nightlife & Drinks: $10–$20 (depends how fancy you get)
If you splurge on fancy cocktails or shopping, obviously, the budget jumps, but if you stick to hawker food and free attractions, you can experience Singapore without burning a hole in your wallet.
Final Thoughts – Why Singapore is a DIY Wanderer’s Paradise
Singapore is more than just a stopover city. It’s a place where old meets new, luxury meets tradition, and adventure is around every corner. Whether you’re standing on top of Marina Bay Sands, wandering through Chinatown, eating your way through hawker stalls, or escaping to Pulau Ubin, this city never stops surprising you.
And with an affordable hotel near downtown, incredible food, and epic sights, all you need is a backpack, a good pair of shoes, and a hunger for adventure.
So, what are you waiting for? Singapore is calling!
