One of the funniest parts of re-reading children’s books as an adult is how relatable the adults are in a very new way. When Mr. Brown says to Paddington Bear, “I appreciate that bear really knows how to find a bargain,” I’m laughing for an entirely different reason than as a kid.
I may not love marmalade but I, too, love a bargain, and that’s why I reached out to The Point | Rachel Lipson. I’m still very new to the world of points and miles—quite honestly fueled by my partner’s business travel—but if you’re feeling like travel is out of reach, there are ways to optimize into some incredible experiences. Like extreme couponing points is work but the payoff is pretty sweet, as someone who recently stayed at the Ritz-Carleton Turks and Caicos 100% on points which was as lovely as you would expect a luxury property to be.
Rachel Lipson on Travel with Toddlers
Rachel Lipson from The Point.
I appreciate that there’s lots of points and miles gurus out there. But I think there’s something important about another parent helping you out on points and miles. I don’t just want to know how to use points better; I want to know kid-friendly places to use my points.
Rachel is based in Park Slope, Brooklyn, with her husband, ten and twelve year old boys, and a windsprite pup. She’s not just a points expert—she’s also the founder and CEO of a songwriting school for kids. They’ve been EVERYWHERE and I’m hoping I can use some of these tips myself!
Do you travel often? What’s your travel “style” before and after kids?
We travel so often. Sometimes I think too much! The kids are in school so we typically travel around their school schedules, but often take a few days on either end of a break to get a little more out of each trip. I value education above all but I also believe there are different ways kids learn — and travel is one of the best ways.
Before kids, I worked 15+ hour days and didn’t really have enough time (or money!) to take many trips. Most of our trips were to visit family. Now we take multiple international trips a year and we also go see family in between.
Okay, let’s talk points! How do you get points in the first place, or enough to actually make it worthwhile?
It’s never too late to get started with points! Whether you use points for one trip or for many throughout the year, the most important thing is that they unlock something for you that may not have been possible. That could be a free trip, or it could be a more luxe experience, or maybe it’s a destination you wouldn’t have considered before. There is not 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 earn 5,000 points(ish). If you instead, put that same $5,000 on a new card over the course of a few months, you can 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 search for trips differently, and how does it impact traveling with little ones specifically?
Points have opened up a whole world of possibilities for us. We’ve taken trips to places we hadn’t considered because we found a great deal, booked stopovers in cities like Paris and Amsterdam that we’ve been able to return back to again and again, and taken so many more trips in a year than we ever thought possible.
When it comes to traveling with kids, points and miles are what has made it possible. We often fly business class for less than the price of economy. We stay in five-star hotels with gorgeous pools and spas and often book two rooms so everyone has a bed—typically all on points. (Editor’s note: The dream!!)
What’s your biggest piece of advice when traveling with a baby?
I hired a sleep coach when my oldest was a baby and an impossible sleeper. We brought him to bed with us on a trip after working tirelessly (literally) to get him to sleep alone. When I told her, she said what happens on vacation stays on vacation. Reset and go back to your normal routines when you get back home. I’ve carried this advice with me through all the phases of my kids’ childhood.
Also, remember if your baby is crying it’s way worse for you, the one who has to spring to action, than for anyone else.
What about when they get a little older? How did you manage two under two?
My kids are two years apart so when they were little (and honestly even now) I’d put them next to each other or myself in between them in a row on a plane and found it way easier to keep the occupied without having to worry about bothering a neighbor. My husband would sit across the aisle instead of doing two and two. It worked for us and I recommend trying it, and ideally trading off who sits with the kids. Also, take turns sleeping on long flights if you have a partner. You will each have more patience if you have rest.
The best destination to travel with kids is…
The easiest and most comfortable city we’ve visited is Amsterdam. In terms of a beach trip, we love Papagayo in Costa Rica! There is so much to do without leaving the peninsula! For a unique more culturally oriented experience, we’ve loved Cartagena and Marrakech. There is nothing like seeing the world through your kids’ eyes.
And if we’re talking just on points, The Ambassador suite at the Park Hyatt Paris in the top. Our room combination was $0 since it was fully booked on points but would have been over $7,000 a night.
And the best kid-friendly hotel is…
The Udvar Parisi Budapest (a Hyatt hotel) upgraded us from a basic room to a two bedroom two bathroom suite. There is nothing like having space when you travel with kids! The Grand Hyatt in Berlin gave the kids an assortment of robes, slippers, toys and all kinds of little toys and cookies. The Park Hyatt Milan had a candy bar waiting for the kids. These little details make the trip so much fun for the kids and make us feel like they are welcome.
Tell me your most epic fail while traveling with kids, and how you recovered.
There’s always something that can go wrong! There was the time we checked out of our hotel just in time to catch the high speed train from Venice to Milan and managed to go to the wrong train station. Recently, I thought I booked a hotel stay but realized I accidentally canceled it weeks before and then had to figure out another plan a few days out from the trip.
By far the worst experience, though, we had traveling was when our son was diagnosed with a staph infection one hour before leaving on a one month trip to Italy. Luckily, points actually saved us (as did our travel insurance annual plan!) and after he was discharged from the hospital a week later, we were able to shift things around and make most of the trip still happen. Points create a ton of flexibility.
The top pieces of gear Rachel never leaves home without…
My number one item I would never want to travel without is my extra phone battery charger! We love taking photos, roaming around and staying out all day when we travel. It’s life changing not having to worry about the battery dying. I also love bringing collapsible duffel bags of various sizes. I use them for laundry, bringing back a shopping haul and even just making packing easier when we move around from one place to another.
What’s your favorite memory 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 looking at the photos of us all in various cities over the years.
We didn’t travel as much when the kids were little. COVID-19 hit when they were four and six, and once restrictions lifted, that’s when our travel schedule really took off. But when I think back to those early baby/toddler times, the best feeling was to take a trip with all the gear and stress and worry—but get off the plane on the other side with family, knowing we weren’t alone. ✈️
Thank you so much, Rachel! I’m a JetBlue sun, Marriott rising and I’m definitely going to look deeper into some of our cards and how we’re spending to optimize our points a little more.
Thanks for being here.
The view from our balcony at the R-C.
I’m a total points convert thanks to a spring break stay at The Ritz-Carleton Turks and Caicos a few years ago with my toddler. It was our first big trip on points and I wasn’t sure what to expect, though I’d heard great things about Grace Bay.
Points got us a balcony room that we’d never stay at normally, which was so lovely with an enforced 6:30 PM bedtime. I worried that a luxury resort wouldn’t be toddler-friendly, but the opposite was true. There is nothing nicer 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 down to your lounge chair, just because “I might need it.” Yes, sir, thank you very much! That’s what makes a trip feel like a vacation, not just parenting in another place. That’s worth every point and mile to cash in, in my book.
To 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 thick of the toddler years trying to create core memories for our whole family while minimizing meltdowns—I sincerely hope this helps you do the same.
This post was originally published on Travel with Toddlers. Subscribe for more real-talk travel advice, toddler-friendly itineraries, and tried-and-true gear recommendations.
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