So last November, we brought all the kids over to the US for 4 weeks. After one relatively easy trip with 5 babies under our belt in March, we were feeling pretty confident about doing something ambitious. While discussing which...

So last November, we brought all the kids over to the US for 4 weeks. After one relatively easy trip with 5 babies under our belt in March, we were feeling pretty confident about doing something ambitious.

While discussing which parts of the US to visit, it went something like this:

“Babe what do you think about doing the west coast this time – it’s a little more laid back and easy on the kids.”

“But then Disney!!”

“Is it crazy to do both? We go California then Orlando. We’re saving 5 hours flying into SF anyway, we can definitely handle a 7-hour domestic flight. From there we can wrap up the trip in New York.”

“Yeah, that’s totally doable. Might as well throw in Yosemite and Lake Tahoe.”

“Let’s do it. Go big or go home.”

The itinerary would be San Francisco -> Yosemite -> Lake Tahoe -> Orlando -> New York.

5 kids, 4 weeks, 2 domestic flights, and a road trip – we were either going to lose our minds or it would be the best trip ever.

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First, logistics. There were a lot of moving parts to consider and planning this trip was like fitting them all into a massive puzzle. I’ve done a lot of research so maybe this helps if you’re putting together a similar trip.

Step 1: flights

When you’re flying 2 adults and 5 kids, airline miles are your best friend. I’m obsessive about maximising rewards points on credit card spend and there are tons of blogs covering how to do this. In general, develop a credit card strategy where you’re using cards that earn 4 miles per dollar and then find good redemption options to make the most of those miles.

From Singapore to San Francisco, we managed to snag a redemption for 7 seats on SQ using Krisflyer Spontaneous Escapes for a 30% discount. We then flew back from New York on regular redemption rates. Earning Krisflyer miles are straightforward – all the banks in Singapore partner with Singapore Airlines.

Domestic flight redemption is where you want to be more strategic. You can redeem Krisflyer miles for Star Alliance partner airlines like United but they all price out at 12,500 miles regardless of flight distance, so they’re good for transcontinental flights. For short segments like Orlando to New York, United’s MileagePlus program comes in very handy because it costs just 6,500 miles. Unfortunately, only Standard Chartered transfers to MileagePlus for now so there’s that.

Step 2: road trip

We normally don’t drive in San Francisco (walk/cable car/uber/lyft) but 5 kids put us 1 over the 6-pax rider limit for XL car sharing services, which meant we would need 2 ubers or lyfts to get from point to point. We also weren’t optimistic about walking around too much with 5 jet-lagged kids, so we decided to get a car for the entire California + Nevada segment of the trip. We picked up a car from SFO and dropped it off at Reno airport when we left Nevada.

For car rentals, elite status comes in very handy and you can status match your way to several car rental programs like National Emerald Club, Sixt Platinum and Hertz Gold using hotel status or credit cards. The Citi Prestige card gives you GHA Black, or several Visa Infinite cards sometimes start you out with National status / Hilton fast track.

Alternatively, book via sites like Economy Car Rentals for very decent prices. Remember to check back from time to time as the price fluctuates and you’re allowed to cancel/rebook at the lower price.

I really like road trips – there’s a sense of adventure and you have the benefit of stopping anytime you like to explore hidden gems along the way. We would stop for coffee and sandwiches and snacks and ice cream at little nondescript places in small towns and they were almost always delicious. But the best part was getting to chat with people about what life looks like in a town like Groveland or Oakdale. While getting coffee one time, I met this lady who just had a newborn and we shared a moment exchanging trauma stories about having babies. It was nice to discover that while life can look vastly different sometimes, some experiences are still very much the same.

The other great thing about road trips is that you get to spend long stretches together in a very confined space, which provides unique opportunities for interaction. We would do carpool karaoke or play games or trade jokes or spot animals or just have time to talk.

On the way to Lake Tahoe, we came across the prettiest rainbow and chased it till we got to the end, to determine once and for all if there is indeed a pot of gold at the end of a rainbow. There is not. But the kids had the best time chasing a rainbow, so maybe in a way, there is.

Step 3: packing

I started out determined to pack light but with 5 kids and different climates (we needed clothes ranging from swimwear to ski gear), it was down to finding that sweet spot between sufficient clothing and the amount of luggage we could physically carry, which in this case was 3 suitcases and 2 strollers. And the only way we made this work was to find hotels that had self-service laundry on site every alternate stop – I basically had 4 days worth of clothes for everyone.

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Okay, now for the fun bit.

San Francisco is the perfect spot for the first stop after a transpacific flight. When your brain is still functioning on SG time, you need an itinerary that’s relaxing and easy. To that end, the bay area is gorgeous enough for you to not need constant activity. We spent afternoons walking around the piers watching sea lions, then stopping for hot chocolate and clam chowder.

For the first few days, Finn, Theo and Hayley would rotate nap times on the 2 strollers while Tru and Kirsten powered through the jet lag with us. I love watching the kids try to overcome jet lag because it’s like watching an out of body experience happen in real time. Their eyes would glaze over and I can see their brains checking out of their bodies, like “okay I’m done here, goodnight y’all!”

Every time we sat down for a mid afternoon drink, the kids would slowly fall apart and die a little inside from mind-numbing exhaustion.

We visited the usual attractions like the Golden Gate Bridge, Sausalito, Pier 39, Union Square, Ferry Building, Ghiradelli Square and Land’s End. It was raining intermittently while we were there so we ducked in and out of buildings till the rain stopped.

If you ask the kids, their 2 favourite spots were the Bay Area Discovery Museum and the SF Zoo, both of which happened to be our first visits.

There’s enough stuff at the Bay Area Discovery Museum to keep kids entertained for a whole day, making it the best place to spend a rainy afternoon. It’s got 7.5 acres of indoor + outdoor hands-on, research-backed activities for the kids – it’s fun! and learning! at the same time!

Like this art studio to work on crafty projects.

Theo came running up to show me his mask and I was like “how is this being held to your face so securely?” and he was like “SO EASY…GLUE!!” and it turns out that he glued the mask to his face with SO MUCH GLUE and I was like “NOOOOOOOOOO!!!”

Guess who had to wash off all that glue? Yeah, me.

And this area with puzzles of varying difficulty.

And this area with soft foam building things.

And this indoor skating area.

And this area where they learnt about science.

And this outdoor play area when the rain stopped.

And the most fun area of all, the costume dance party hall.

Thanks to the slight drizzle, the SF Zoo was almost completely empty when we visited so we pretty much had the entire place to ourselves. I think we saw like 3 other families the whole time we were there.

Wide open space to run + no one else around + adorable animals made for a very lovely afternoon indeed.

San Francisco is always a good time and this one was particularly nice because we were all there together. Sure, we had tired babies and occasional squabbles and we had to spend every moment of every day together for 28 days but on the bright side, we got to spend every moment of every day together for 28 days. :)

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