International Men’s Day: Make Singapore the ultimate boys’ trip with this 48-hour guide

Experience Singapore's nightlife with a vintage sidecar ride through vibrant neighborhoods, enjoying sights like Geylang and Chinatown.

Sometimes the boys’ night needs more than another bar, another plan, or the same place as last time. A 48-hour escape to Singapore flips the script: close enough to be easy, packed enough to feel new and fresh, and the right mix of food, rhythm and adventure that always lands differently with the right crew.

Experience a vintage sidecar ride through vibrant neighborhoods, passing iconic spots like Geylang and Chinatown.

You feel it in the quiet hum of Joo Chiat in the morning, pastel shophouses catching the light while you grab kopi and kaya toast before anyone’s awake. You feel it again in the hawker-centre rush with steam, chatter and plates you learn to pronounce only after trying them. And later, in a Chinatown backroom bar where the lights are low, the music slow, and the bartender slides over something you didn’t know you liked.

It all fits together in a way that feels unhurried yet full of character, the kind of getaway where the city meets you exactly where you are. So if you’re ready to let Singapore set the pace, here’s your guide to making those 48 hours count with the boys.

DAY 1

Parkour in the wild at MacRitchie Reservoir

Start your morning with a high-energy hike at MacRitchie Reservoir, inside the Central Catchment Nature Reserve’s 2,000 hectares of forest. With challenging trails, climbs, steps and a canopy bridge, your body will be moving in different ways, almost like parkour in nature. Choose an easy start along the Prunus and Petai boardwalks, push harder on the Chemperai Loop or aim for the TreeTop Walk, a 250-metre suspension bridge hanging 25 metres above the forest floor. Expect birdsong, green light, rustles in the undergrowth and occasional macaque sightings.

Timings:

Prunus, Petai and Chemparai Loop Trails: Monday to Sunday, 7:00 am to 7:00 pm

TreeTop Walk: Tuesday to Friday, 9:00 am to 5:00 pm | Saturday and Sunday, 8:30 am to 5:00 pm

Location: MacRitchie Natural Trail, Singapore

Pro Tip: End your hike with a well-earned breakfast at Roti Prata House on Upper Thomson Road.

Taste Singapore’s culture at Old Bibik’s Peranakan Kitchen

Slow the afternoon down at Old Bibik’s Peranakan Kitchen, a Joo Chiat classic built on generations of Nyonya heritage. The food is bold and handmade, with sambals, pastes and spices carrying lemongrass, galangal, tamarind and belacan. Try Ayam Buah Keluak with its rich, almost chocolatey depth, or Nyonya Laksa, a coconut-based noodle soup filled with spice, prawns and herbs. For something easy, the Nyonya Bento Rice Set covers all bases.

Timings: Monday to Sunday, 11:30 am to 9:30 pm

Location: 328 Joo Chiat Rd, #01-02, Singapore

Pro Tip: Walk to CATA Coffee after your meal for curated weekly brews.

Slow the afternoon down at Old Bibik’s Peranakan Kitchen.

Explore the city’s after-hours DNA with Singapore Sidecars

Kick off the early evening with a vintage sidecar ride through glowing hawker streets, quiet heritage lanes and neighbourhoods that come alive at night. Depending on the route, you may pass Geylang’s neon signs, Chinatown’s late-night eats, Little India’s colours or Kampong Glam’s lantern-lit corners.

Timings: 6:00 pm to 10:00 pm (in 1-, 2- or 3-hour slots)

Location: Shared after booking

Pro Tip: Choose the You Drink, We Drive tour and catch the sunset on a 6:00 pm or 6:30 pm slot.

Close the night with smoke, sizzle and satay at Lau Pa Sat

Once the satay stalls fire up, the whole street transforms. Grab smoky satay sticks from Captain Satay, chicken rice or wonton noodles from Hua Dee Hong Kong Roasted Delight, or dumplings from Lion City Dumpling. The energy is bright, loud and perfect for refuelling at the end of the night.

Timings: 24 hours, Monday to Sunday (individual stall timings vary)

Location: 18 Raffles Quay, Singapore

Pro Tip: One person secures the table while the rest pick the food to keep things moving.

DAY 2

Get your dose of adrenaline at Sentosa

Begin at SkyPark by AJ Hackett above Siloso Beach. Step off the Bungy platform for a clean drop, then try the Giant Swing at 120 km/h. The Skybridge steadies nerves with its transparent floor.

Move to Mega Adventure for MegaZip’s 450-metre ride from canopy to shore, MegaClimb’s treetop ropes and the quick MegaJump free-fall.

Then switch to HyperDrive’s three-storey electric go-kart arena with boosts, power-ups and sharp overtakes. Refuel at HyperDrive Café between races.

Timings:

SkyPark by AJ Hackett: Monday to Sunday, 11:30 am to 7:30 pm

Mega Adventure Park: Monday to Sunday, 11:00 am to 6:30 pm

HyperDrive: Monday to Friday, 12:30 pm to 9:00 pm | Saturday and Sunday, 10:00 am to 9:30 pm

Locations:

SkyPark by AJ Hackett: 30 Siloso Beach Walk, Sentosa Island

Mega Adventure Park: 10A Siloso Beach Walk, Sentosa Island

HyperDrive: 54 Palawan Beach Walk, The Palawan @ Sentosa

Pro Tip: Book in advance and plan activities by zone to maximise time.

Settle in for lunch at Trapizza Singapore

Cool off at Trapizza on Siloso Beach with thin-crust pizzas, pastas and chilled drinks. It’s the perfect reset after a high-energy morning.

Timings: Monday to Thursday, 12:00 pm to 9:00 pm | Friday to Sunday, 11:00 am to 10:00 pm

Location: Level 1, 101 Siloso Road, Sentosa

Pro Tip: Head to Ola Beach Club after lunch for jetblading, paddleboarding, kayaking or a quiet poolside drink.

When the sun sets, dive into a speakeasy bar crawl

Start at Taylor Adam, a tailor shop in front and speakeasy inside. Try Oh My Ducky.

Next is The Secret Mermaid, hidden behind an unmarked basement entrance. Try Dracola.

Move to Employees Only, the Singapore outpost of the New York icon with a tarot reader at the entrance. Try Swizzle Express.

End at Sago House, a raw loft with weekly rotating cocktails and vinyl vibes.

Timings:

Taylor Adam: Monday to Saturday, 5:00 pm to 12:00 am

Secret Mermaid: Monday to Friday, 5:00 pm to 11:00 pm

Employees Only: Monday to Friday and Sunday, 5:00 pm to 1:00 am | Saturday, 5:00 pm to 2:00 am

Sago House: Sunday to Friday, 6:00 pm to 1:00 am | Saturday, 6:00 pm to 2:00 am

Locations:

Taylor Adam: 1 Raffles Pl, #01-03

Secret Mermaid: 10 Collyer Quay, B1-09 Ocean Financial Centre

Employees Only: 112 Amoy St

Sago House: 37 Duxton Hill

Pro Tip: Maxwell Hawker Centre is a short stop for quick bites like satay, oyster omelette or chicken rice between bars.