How to Travel with a Toddler Using Points and Miles

One of the most fun aspects of rereading children’s books as an adult is how adults can relate to them in a whole new way. When Mr. Brown says to Paddington Bear, “I like that bear really knows how to find a good deal,” I laugh for a completely different reason than when I was a kid.

I may not like marmalade, but I love a good deal too, and that’s why I contacted The Point | Rachel Lipson. I’m still very new to the world of points and miles—honestly fueled by my partner’s business travel—but if you feel like travel is out of reach, there are ways to maximize incredible experiences. Like extreme couponing points, it’s work but the reward is rather interesting, as someone who recently stayed at the Ritz-Carleton Turks and Caicos 100% on points which was as charming as you would expect in a luxury property.

Rachel Lipson on traveling with toddlers

Rachel Lipson of The Point.

I like that there are a lot of points and miles gurus. But I think there’s something important in another mother help you with points and miles. I don’t just want to know how to use points better; I want to know about kid-friendly places to use my points.

Rachel lives in Park Slope, Brooklyn, with her husband, boys ages ten and twelve, and puppy Windsprite. She’s not only a stitch expert, she’s also the founder and CEO of a children’s songwriting school. They went EVERYWHERE and I hope I can use some of these tips myself!

Do you travel often? What is your travel “style” before and after children?

We travel so often. Sometimes I think too much! The kids are in school, so we usually travel around their school schedules, but we often take a few days off at the end of each vacation to get a little more mileage out of each trip. I value education above all, but I also believe that there are different ways for children to learn – and travel is one of the best.

Before having kids, I worked 15+ hour days and didn’t really have enough time (or money!) to do a lot of traveling. Most of our trips were to visit family. Now we take several international trips a year and we also go see family in between.

Okay, let’s talk about points! How do you get points in the first place, or enough to make it worth it?

It’s never too late to start earning points! Whether you use points for a single trip or multiple ones throughout the year, the most important thing is that they unlock something for you that might not otherwise have been possible. It could be a free trip, or a more luxurious experience, or maybe a destination you wouldn’t have considered before. There is no one way to use points: the best way to use them is the way that works for you.

The easiest and quickest way to earn points is with a welcome bonus on a new credit card. If you spend $5,000 on a card you already own, you’ll earn 5,000(ish) points. If, instead, you put that same $5,000 on a new card over the course of a few months, you can earn more than 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? Are you looking for travel differently and how does that impact traveling with toddlers specifically?

Points opened up a whole world of possibilities for us. We took trips to places we hadn’t thought about because we found so much, booked layovers in cities like Paris and Amsterdam that we could return to again and again, and did way more trips in a year than we ever thought possible.

When it comes to traveling with kids, it’s points and miles that made it possible. We often fly business class at a lower price than economy class. We stay in five-star hotels with great pools and spas and often book two rooms so everyone has a bed, usually on points. (Editor’s note: The dream!!

What’s your biggest tip 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 on his own. When I told her she said what happens on vacation stays on vacation. Reset and resume your normal routines when you return home. I have carried this advice with me through all phases of my children’s childhood.

Also remember that if your baby cries, it’s much worse for you, the one who has to take action, than for anyone else.

And when they’re a little older? How did you manage two less than 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 in a row on a plane and found it much easier to keep them occupied without having to worry about disturbing a neighbor. My husband would sit across the aisle instead of doing two and two. This worked for us and I recommend trying it, and ideally choosing 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 rest.

The best destination to travel with children is…

The easiest and most comfortable city we have visited is Amsterdam. Beach-wise, we love Papagayo in Costa Rica! There are so many things to do without leaving the peninsula! For a unique and more cultural experience, we loved Cartagena and Marrakech. There’s nothing like seeing the world through your children’s eyes.

And if we’re just talking about points, the Ambassador Suite at Park Hyatt Paris up. Our room combination cost $0 because it was fully booked in points, but it would have cost over $7,000 a night.

And the best kid-friendly hotel is…

Udvar Parisi Budapest (a Hyatt hotel) upgraded us from a basic room to a two bedroom, two bathroom suite. There’s nothing like having space when traveling with kids! The Grand Hyatt in Berlin gave the children an assortment of bathrobes, slippers, toys and all kinds of small toys and cookies. The Park Hyatt Milan there was a candy bar waiting for the children. These little details make the trip a lot of fun for the children and make us feel welcome.

Tell me about your most epic failure while traveling with kids and how you recovered from it.

There is always something that can go wrong! There was the time we left our hotel just in time to catch the high-speed train from Venice to Milan and managed to take the wrong station. Recently, I thought I had a hotel stay booked, but realized I had accidentally canceled it weeks before and then had to come up with another plan a few days into the trip.

However, the worst experience we had while traveling was when our son was diagnosed with a staph infection an hour before leaving for a month-long trip to Italy. Luckily, the points saved us money (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 keep most of the trip going. The points create a ton of flexibility.

The best equipment Rachel never leaves the house without…

My number one item I would never want to travel without is my extra phone battery charger! We love taking photos, walking around, and staying outside all day when we travel. It’s life changing without having to worry about the battery dying. I also like to bring collapsible duffel bags in different sizes. I use them for laundry, to bring back groceries, and even just to make packing easier when we’re moving from one place to another.

What is your best travel memory with your children?

Here we are in Stockholm! We try to book a photographer once a year when we travel. It’s amazing to have photos of the four of us and I love looking at the photos of all of us in different 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 days with babies and toddlers, the best feeling was taking a trip with all the gear and stress and worry, but getting off the plane on the other side with family, knowing we weren’t alone. ✈️

Thank you very much, Rachel! I’m a JetBlue Sun, Marriott upwards and I’m definitely going to dig into some of our cards and how we spend to maximize our points a little more.

Thanks for being here.

The view from our balcony at the RC.

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. This was our first big points trip and I wasn’t sure what to expect, even though I had heard great things about Grace Bay.

Points gave us a room with a balcony that we would never normally stay in, which was so lovely with a forced 6:30pm bedtime. I was worried that a luxury resort wouldn’t be toddler-friendly, but the opposite is true. There’s 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 to your lounge chair, just because “maybe I need it.” Yes, sir, thank you very much! It’s what makes a trip feel like a vacation, not just like being a parent in another place. It’s worth every point and every mile to cash in, in my opinion.

To pina coladas and getting caught in the rain,

Kayla

If you liked this article, please consider supporting my work. I’m just a mom at heart trying to create essential memories for our entire family while minimizing meltdowns. I sincerely hope this helps you do the same.

This article was originally published on Traveling with Toddlers. Subscribe for more actionable travel tips, toddler-friendly itineraries, and proven gear recommendations.

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