Passports and Eyerolls

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As Far As You Can Go Before Coming Back

A strategic port for centuries, home to pirates and typhoons.
Now a gleaming metropolis, still strategic, still a port, home to a massive service economy, more than a few tycoons…and typhoons.

From the U.S. East Coast, getting to Singapore is a long, seemingly infinite day. First, a flight to San Francisco. Then a 17-hour haul across the Pacific and the International Date Line. It’s about as far as you can go before you start coming back.

Dan, the boys, and I landed at 5:45 a.m. in the sparkly efficient machine that is Singapore Changi Airport. For a massive global hub, it is astonishingly streamlined especially if you’re traveling carry-on only (ahem….IAD…side-eyeing you). If we hadn’t gone hunting for the Rain Vortex, we could have been from plane to curb in about ten minutes.

(Maybe Don’t Go…) Chasing Waterfalls at 5:45AM

Changi’s Jewel Rain Vortex is a tourist attraction in its own right, and since it was so early, I assumed it would be worth a quick look before heading to the hotel. Had I bothered to check the clearly posted hours, I would have known it doesn’t officially open until 10 a.m. The resulting eyerolls and grumbles were, this time, fully justified.

Disappointment managed, we paused to get the teen and me set up with our Saily eSIM (full review coming) and I downloaded Grab—Southeast Asia’s answer to Uber. (Aside: After nearly three weeks of using it across multiple countries, I can confidently say it might actually be better.) While Singapore’s MRT is fast, clean, and incredibly efficient, exhaustion won this round; public transit exploration would have to wait.

The Fullerton: A Splurge and a Splash

Soon enough, we were on our way to The Fullerton Hotel. This was another assist from the incredible Geraldine Hastings of Virtuoso Travels (more on why having an expert in your corner matters here). Dan would be joining us in Singapore to ring in the New Year and send us off on our longer journey. New Year’s Eve fireworks were also the tween’s number-one wish. Combined, this pushed Singapore firmly into the “splurge” category.

Aside from Marina Bay Sands, which requires a seven-night minimum around the holidays, I was at a loss for where to stay in order to tick off everyone’s wish lists. Enter Geraldine. I gave her my parameters: fireworks views and a great pool.

She delivered. The Fullerton Hotel was the perfect choice. Built on the site of Fort Fullerton, the heritage property was completed in 1928 and once housed the General Post Office along with several key government offices (yes, I read the plaque….it’s a thing). Fully renovated, modern yet respectful of its history, and centrally located, The Fullerton was an ideal launching point for the trip.

Dazed, Confused and Chawanmushi

Because we arrived so early, our rooms weren’t ready, but the staff, clearly accustomed to glassy-eyed travelers, pointed us toward breakfast and graciously offered access to the gym and spa facilities so we could freshen up.

Breakfast was a true smorgasbord, with options spanning Western and Asian cuisines. The boys, always adventurous eaters (a major asset on this trip), quickly embraced rice and noodles for breakfast. Yes, please! I even indulged in my favorite chawanmushi most mornings, followed by strong coffee and a pain au chocolat—because why not?

Welcome to the Jungle (Only With Skyscrapers)

Fortified, if not fully recovered, I herded everyone out of The Fullerton’s cool, climate-controlled calm and into the sweltering embrace of Singapore’s streets. Singapore sits closer to the equator than anywhere else on our itinerary, and even for a family from the USA’s mid-Atlantic, the humidity was intense. December through early March is monsoon season, followed by a second monsoon from June through September. Even the “dry” months feature frequent afternoon downpours. Translation: pack an umbrella. You can pave over the jungle, but you can’t quite remove it from the city – I’ll workshop that line.

Most sane trip planners might opt for a gentle riverside stroll on day one. Not me! I know my people. If I didn’t keep them moving, jet lag would win. So, in an act of true maternal love, I booked a four-hour culture and food tasting tour. On foot.

I adore starting trips with walking tours. Many cities offer free ones (tip your guides, please), and they’re a great way to orient yourself while absorbing history and culture. In this case, I was also eager to dive into Singapore’s food scene.

Kampong Glam

We met our guide, Marcus, in Kampong Glam. History time! The district was granted to Sultan Hussein Shah and his followers by the British East India Company in 1819 and became an enclave for the Malay Muslim community (sarcasm alert..how generous of the colonizers). The neighborhood centers on Sultan Mosque and Haji Street.

Fun fact (cue the eyerolls) the current Sultan Mosque was built over the original 1826 structure and funded largely through community donations. The green band beneath the golden dome is made of bottle ends. Officially, they’re soy sauce bottles. Local lore suggests… maybe not.

Our first tasting focused on Malay cuisine and was a halal establishment. It’s important to note that many establishments in both Singapore and Malaysia are halal; the food is delicious but be aware that haram substances (including alcohol) will not be available. Speaking of beverages, this is also where the boys were introduced to the Southeast Asian staple drink, 100+. It tastes like a cross between Sprite and Ting and is more refreshing than water in the heat and it is marketed as a “health” drink so, since it’s now their go-to, that’s the narrative we are sticking with.

We zipped through Haji Street known for its dramatic street art (Singapore’s only legal graffiti zone), boutiques, and trendy vibes. Definitely a place to revisit at a slower pace. Next stop: Little India, via the MRT.

Riding the Rules

While that might not sound thrilling, having a local guide walk us through the MRT system was invaluable. It’s massive, spotless, and inexpensive. Even the boys commented that it far surpassed any public transit system back home (looking at you, DC Metro and NYC subway).

This was also when they started noticing Singapore’s many rules. Marcus pointed out where to stand, where to sit, and how to behave. He gestured to the cameras, the “hidden eyes” and explained that violations lead quickly to fines, and some crimes to caning. As the trip went on, the boys began connecting the pristine cityscape, no trash, no graffiti, no visible homelessness, with the trade-offs in personal freedom and started asking whether the results were worth the cost.

Little India

Stepping off the MRT into Little India felt like entering another world. While Singapore emphasizes harmonious multiculturalism, it’s clear each group fiercely preserves its identity. Little India sounded, and in some ways looked, like the India of my childhood, just cleaner and minus the roaming cows.

Little India was also our first hawker center – a Singapore staple also arising for the need for cleanliness and order. Prior to the organization of hawker centers most of the local vendors could be found on the streets. A sight common everywhere else in Asia but not in keeping with Singapore’s image of itself.   Marcus taught us hawker center etiquette: tables are claimed with tissues, napkins, or umbrellas. He returned with a spread of Indian dishes and instantly earned the teen’s loyalty by adding mango lassis. He also pointed out the washing stations for cleaning hands before and after meals as well as where and how to return the trays, plates and utensils. Reminding us that the “gamen” was always watching and, once again, not following the rules could result in fines.

Once we finished our meal and put away our trays (properly!), we dodged the vestiges of rain by hopping back on the MRT and heading to our final stop: Chinatown.

Chinatown

Another entirely distinct enclave, with its own look and energy. Marcus explained the difference between the Peranakan Chinese, early settlers who arrived between the 1400s and 1500s and intermarried with the local Malay population, and the later waves of Chinese laborers in the 1800s. Both shaped Singapore profoundly yet retain distinct cultural identities.

Our final hawker center featured two Michelin-recognized stalls: one for satay, the other for spring rolls. We were skeptical. “It’s meat on a stick,” the teen shrugged. “How good can it be?”
Very. Very good. And those spring rolls alone may have justified the entire never-ending day.

Wild Horses Couldn’t Keep Us Up Anymore

By late afternoon the tour had ended. We bid Marcus adieu and I deemed it safe to return to the hotel. I forced (never thought I’d say that) the boys into The Fullerton’s gorgeous pool. Dan promptly snuck off and fell asleep, a decision he would regret for the rest of the trip, though, to be fair, he was also battling a cold.

By 6 p.m., the boys surrendered completely and begged for bed. We kept them upright just long enough to eat, and then, suddenly, the long seemingly unending day was done.