Adventurous Long Weekend Exploring Singapore

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Advisor - Dan Cogan
Curated By

Dan Cogan

  • Singapore

  • Arts & Culture

  • Couples Travel

  • City Travel

  • Food & Wine

  • Wellness Travel

  • Bucket-List

  • Sightseeing

  • Shopping

aerial view of gardens and large white structure
Curator’s statement

This was one of the wildest weekends that my wife and I have pulled off. After many years of proving we love taking long weekends in Europe, without major jetlag or setbacks, we decided to up the ante and see if we were strong enough for 43 hours of flying in five days. Spoiler: we were and you are too! Singapore is a fantastic city with amazing food and culture and is a great place to spend a three-day weekend. We loved the vibrant markets, the warm climate and the lush gardens.

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Days 1 & 2: Travel to Singapore

aerial view of buildings during sunset

Day 1

It's Wednesday, you are about to embark on an epic journey. We live in Chicago but this is accessible from anywhere in the United States pretty much the same way. We built in a six-hour layover in San Francisco so we could have dinner with some friends. This is your adventure so you can do it your way and leave after work on Wednesday. You just have to get to SFO in time to make the connection to Singapore at 10:45pm.

Day 2

You're going to spend pretty much this entire day in flight. It's 17 hours from SFO to SIN. Bring lots of work to do, it's actually a great time to clean up that email inbox and get lots of work done. There's plenty of time for sleep too...and movies...and three meals...don't forget to get up and take some walks around the plane. We specifically chose this route because United flies the Boeing 787 on it and it is much better on your body.

Day 3: A day at the spa

ferris wheel next to buildings at nighttime

You've made it! It's 8:00 am Friday morning in Singapore and you only have a carry-on so head directly to customs. You just spent 24 hours in travel, so go check in to the hotel (they're expecting you), and then it's time to head to the spa! This is an absolute must: you should make a reservation at the Tempat Senang Spa Resort. It's a ferry ride from Singapore but you're ready for the fresh air.

Once there, indulge the rest of the morning in three spa treatments. They also have a wonderful restaurant to have lunch at before heading back to Singapore.

It's late in the afternoon by the time you return from the spa. If you're up for it, you should hop on the Singapore Flyer, the views are incredible. Then rest up and get ready for dinner. We chose to take it easy this night and had a wonderful dinner at a restaurant called Southbridge, which had amazing oysters and maybe an even more amazing view! Then it was back to the hotel for a good night's sleep.

Day 4: Visit Gardens by the Bay & explore Chinatown

purple lights standing on tall structures in the night sky

You have two full days left and there is no shortage of activities to enjoy in Singapore. After breakfast, start your day strategically by visiting the Gardens By the Bay, this place is absolutely stunning, there are over a million plants there and it features the Supertree Grove.

You have some time to explore the bayfront, go check out the Louis Vuitton there, it's a must-see-to-believe store on the water! Now head off to Chinatown for some lunch, and graze your way through Chinatown. There is no shortage of delicious options to try here. Don't be afraid to step out of your comfort zone. Kug Pao Frog legs? YES!

Fellas, if you're ever here, buy a suit or blazer or more! There is no shortage of awesome tailors with amazing fabrics at reasonable prices. I bought a blazer from the guys at Raffles. Definitely check out the Sri Mariamman Temple while there.

Back to the hotel for a little rest and relaxation if you need it before dinner. You may be sweaty and a little tired at this point, head back to the hotel for pool or spa time. Then head back out for dinner at Hawker food centers in Singapore; Newton Food Center is my favorite but you should definitely follow your gut (pun intended). The food centers are a dizzying array of sights, smells and sounds and we sampled no less than 20 different dishes while catching up with some ex-pat friends over many cold Tiger Beers. I think my favorite was the chili crab but the oyster omelet was shockingly delicious. Don't be scared, just go for it! We then went back to Chinatown to walk off dinner and do a little night shopping before bed.

Day 5: Full day of sightseeing

people in pool overlooking the city

Last day in Singapore, make it count! Start your day with a good breakfast at your hotel before heading out for a walk down Orchard Road for some shopping. The world's top brands all have shops here, so window shopping is the way to save but there is no shortage of splurge-worthiness options on this road. Gucci, LV, Hermes, Chanel, you name the brand and they have a flag planted on this road.

I highly recommend a trip to the Singapore Botanic Gardens to see the orchids, it's a once-in-a-lifetime experience. Light lunch only on this day so we can explore Little India and have dinner there.

Start with a visit to the Sri Veeramakaliamman Temple, it's so colorful and unique and at the same time serene. Then shop your way down Serangoon Road for souvenirs, spices and maybe even some jewelry (don't be afraid to haggle). You will want to just wander, do it, but don't skip the Abdul Gaffor Mosque, it's spectacular! There are several other temples to visit in Little India while you wander and work up that appetite! If you don't like Indian Food then hop in an uber/cab and head to Burnt Ends for some of the world's best BBQ.

If you like Indian Food then you are in for a treat! We absolutely loved the Banana Leaf Apolo, the curries were out of this world! This day has been so fun but it's back to the hotel (they've saved you a day room) to shower and freshen up for the flight home. Here's the weird part, you're going to live this day twice, the second time on a plane! You depart Singapore at 9pm on Sunday and land in San Francisco at 9:10pm Sunday night, congratulations on becoming a time traveler! Time for a redeye back to your home airport and you'll be back at work Monday morning.

Need to Know

If you're not staying at the Marina Bay Sands then you have to at least go visit the bar that's on the pool level so you can see it. If you are staying there then I know you already swam in it and took a thousand pictures for insta (that's what we did).

Advisor - Dan Cogan

Travel Advisor

Dan Cogan

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