One of the funniest parts of rereading children’s books as an adult is how adults can relate to them in new ways. When Mr. Brown said to Paddington Bear, “I appreciate that bears really know how to get a bargain,” I laughed for a completely different reason than I did when I was a kid.
I may not like marmalade, but I also like a bargain, and that’s why I contacted The Point | Rachel Lipson. I’m still very new to the world of points and miles—honestly driven by my partner’s business travel—but if you feel like travel is out of reach, there are ways to optimize a great experience. Like extreme coupon points Work but the reward was quite sweet, like someone who had just stayed there Ritz-Carleton Turks and Caicos 100% on point as beautiful as you would expect from a luxury property.
Rachel Lipson on Traveling with Toddlers
Rachel Lipson of The Bottom Line.
I appreciate that there are many points and miles experts out there. But I think there’s something important about something else parent helps you with points and miles. I don’t just want to know how to use points better; I’d like to know a kid-friendly place to use my points.
Rachel lives in Park Slope, Brooklyn, with her husband, sons ages ten and twelve, and puppy Breeze. He’s not just a point expert—he’s also the founder and CEO of a songwriting school for kids. They are EVERYWHERE and I wish I could use some of these tips myself!
Do you travel often? What was your travel “style” before and after having kids?
We travel a lot. Sometimes I think too much! The kids are at school so we usually travel around their school schedule, but often we take a few days at the end of each break to get more out of each trip. I value education above all else, but I also believe there are many ways for children to learn — and travel is one of the best ways.
Before having kids, I worked 15+ hours a day and didn’t have enough time (or money!) to travel much. Most of our trips are visiting family. Now we take several international trips a year and we also visit family in between.
OK, let’s talk points! How do you get points, or enough to make it worthwhile?
It’s never too late to start with points! Whether you use points for one trip or for many trips throughout the year, what’s most important is that they open up something for you that you might not otherwise be able to do. It could be a free trip, or a more luxurious experience, or perhaps a destination you’ve never considered before. There’s no one way to use points—the best way to use them is the way that works for you.
The easiest and fastest way to earn points is through a welcome bonus on a new credit card. If you spend $5K on a card you already have, you’ll get 5,000 points(ish). If you put that same $5,000 into a new card over a few months, you could earn 75,000+ points. The card I recommend everyone get if they don’t already have it is this one.
How do points impact your travel planning? Do you explore travel differently, and what impact does this have on traveling with young children in particular?
Points have opened up a lot of possibilities for us. We’ve traveled to places we hadn’t considered because we discovered so much, booked stops in cities like Paris and Amsterdam so we could return again and again, and done more traveling in a year than we ever imagined.
When it comes to traveling with kids, points and miles are what make it possible. We often fly business class at prices cheaper than economy. We stayed at five-star hotels with beautiful pools and spas and often booked two rooms so everyone had a bed—usually everything was on points. (Editor’s Note: The dream!!)
What is your biggest piece of advice when traveling with a baby?
I hired a sleep coach when my oldest was a baby and had trouble sleeping. We took him to bed with us on trips after working tirelessly (literally) to get him to sleep alone. When I told him, he said what happens on holiday remains on holiday. Reset and return to your normal routine when you return home. I have carried this advice through all phases of my children’s childhood.
Also, remember that if your baby cries, it is worse for you, as the person who has to take action, than it is for anyone else.
What about when they get older? How do you set two under two?
My kids are two years apart, so when they were little (and honestly even now), I would put them next to each other or myself between them in one row on the plane and found it easier to stay busy without having to worry about disturbing the neighbors. My husband will sit across the aisle rather than do two and two. This worked for us and I recommend trying it, and ideally swapping who sits with the kids. Also, take turns sleeping on long-haul flights if you have a partner. Each of you will have more patience if you rest.
The best destinations for traveling with children are…
The easiest and most comfortable city we have visited is Amsterdam. When it comes to beach trips, we love Papagayo in Costa Rica! There are lots of things to do without leaving the peninsula! For unique experiences that are more culturally oriented, we like Cartagena and Marrakech. There’s nothing like seeing the world through your children’s eyes.
And if we’re just getting down to the bullet points, The Ambassador suite at Park Hyatt Paris on. Our room combination was $0 because it was fully booked on points but would have been over $7,000 per night.
And the best kid-friendly hotels are…
Udvar Parisi Budapest (Hyatt hotel) upgraded us from a basic room to a two bedroom two bathroom suite. There’s nothing like having space when you’re traveling with kids! Grand Hyatt in Berlin gave the children an assortment of robes, slippers, toys, and all kinds of small toys and cakes. Park Hyatt Milan have candy waiting for the kids. These little details made the trip really fun for the kids and made us feel welcome.
Tell us about your biggest failure while traveling with kids, and how you recovered.
There’s always something wrong! There was the time we checked out of the hotel just in time to catch the high-speed train from Venice to Milan and managed to get to the wrong train station. Recently, I thought I booked a stay at a hotel but realized I accidentally canceled it weeks before and then had to think of other plans a few days into the trip.
However, by far the worst experience we had while traveling was when our son was diagnosed with a staph infection an hour before leaving on a month-long trip to Italy. Luckily, points really saved us (as did our annual travel insurance plan!) and after he was released from the hospital a week later, we were able to turn things around and make the most of the trip still happen. Points create a lot of flexibility.
Rachel’s best gear is never leaving the house without…
The number one item I don’t want to travel without is an extra cell phone charger! We love taking photos, wandering around, and being out all day while traveling. It’s life changing without having to worry about the battery running out. I also like to carry collapsible duffel bags of various sizes. I use it for laundry, bringing back groceries, and even just making packing easier when we move from one place to another.
What are your favorite memories of traveling with your kids?
Here we are in Stockholm! We try to book a photographer once a year on our travels. It’s amazing to have photos of the four of us and I love seeing photos of us all in different cities over the years.
We didn’t travel much when the kids were little. COVID-19 hit when they were four and six years old, and once restrictions lifted, that’s when our travel schedule really took off. But when I think back to those early baby/toddler days, the best feeling was traveling with all the gear, stress, and worries—but getting off the plane on the other side with family, knowing we weren’t alone. ✈️
Thank you so much, Rachel! I’m the JetBlue, Marriott sun is rising and I’m definitely going to take a deeper look at some of our cards and how we spend money to further optimize our points.
Thank you for being here.
The view from our balcony at RC.
I got the total point conversion thanks to spring break in Ritz-Carleton Turks and Caicos a few years ago with my toddler. It was our first big trip in terms of points and I wasn’t sure what to expect, even though I had heard great things about Grace Bay.
Points got us a balcony room we would never normally have, which was lovely with the enforced 6.30pm bedtime. I was worried that luxury resorts would not be toddler friendly, but the opposite was true. There’s nothing better after waking up at dawn with a toddler than someone seeing how tired you are and asking if you’d like breakfast and coffee brought to your lounge chair, just because “I might need it.” Yes sir, thank you very much! That’s what makes travel feel like a vacation, not just babysitting somewhere else. It’s worth every point and mile to cash in, in my book.
For pina coladas and getting caught in the rain,
Kayla
If you liked this post, please consider supporting my work. I’m just a mom in the toddler years trying to create core memories for our entire family while minimizing the meltdowns—I really hope this helps you do the same.
This post was originally published on Traveling with Toddlers. Subscribe for more real-life travel advice, toddler-friendly itineraries, and tried-and-true gear recommendations.
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