In the summer of 2016, I packed up my four kids (ages 18 months, 4, 6, and 9) and “moved” to Europe for nearly three months. Without my husband.

Here’s the quick backstory: My husband and I had sold our house in Colorado and were trying to figure out where we wanted to live next. He worked in the oil and gas industry and was regularly gone for months at a time anyway, so I figured if I was going to be on my own with four kids, I might as well do it somewhere interesting. In fact, my motto became: If we’re going to be crazy anyway, we may as well do it somewhere cool.

We spent about six weeks in Pula, Croatia, followed by another month or so in Marseille, France. It was chaotic, parts of it were awful, and it was also one of the best things I’d ever done.

Ten years later, we are still going strong. My kids have been to more than 30 countries. We’ve trekked part of the Inca Trail to Machu Picchu, hiked an active volcano in Guatemala, bungee jumped in Ecuador, ridden camels and glamped in the Sahara, surfed in Costa Rica, and practically skinny-dipped in a hot spring in the mountains of Iceland. Points and miles made a lot of that possible, but my award travel strategy today looks pretty different than it did when my kids were little.

 

I Used To Do Almost Anything To Stretch a Trip

 

You might assume that traveling alone with four little kids made me prioritize convenience. You would be wrong.

I was cheap. Painfully cheap (still am a bit, too). Even though points and miles seemed to grow on trees back then, I guarded mine like they were a scarce natural resource. I searched for the cheapest awards, took terrible routings, stayed at cheap hotels, and tried to squeeze as much travel as possible out of every point. Sometimes, I even saw an objectively terrible itinerary as an opportunity.

In 2019, I was looking for United award flights home from Costa Rica when I found an itinerary with an 18-hour layover in El Salvador. We’d never been there, and I figured we probably weren’t going to plan an entire trip around El Salvador anytime soon, so naturally, I booked it.

It wasn’t until later that I really thought through the logistics. We had to leave our hotel in Costa Rica at 3:30 a.m., and our flight out of El Salvador didn’t leave until around 1 a.m.

Somehow, it worked. We arrived in San Salvador, checked into a hotel ridiculously early, took a much-needed nap, ate pupusas, and spent the day exploring. El Salvador became my kids’ 19th country.

I’m glad we did it. I’m also pretty confident that if I saw that itinerary today, I’d keep scrolling.

 

My Kids Could Handle More Than I Thought

 

Part of the reason I continued traveling this way was that my kids kept proving they could handle whatever ridiculous plan I came up with.

During one trip to Guatemala, I decided somewhat spontaneously that we couldn’t leave without visiting Tikal. Google Maps said it would take about nine hours to drive there from Antigua. Construction and traffic turned that into nearly 12 hours.

We spent the night in Flores, drove another hour the next morning, and then spent the day climbing around the ruins in the heat. I kept expecting the kids to be done, but every time I thought they’d had enough, they wanted to climb another pyramid. Then we got back in the car and eventually did the whole drive in reverse.

There were plenty of trips like that. Early mornings, long travel days, weird accommodations, missed plans, and rental-car mishaps were just part of the deal. We’ve had a horse run off with one of my kids in Ecuador, pushed a woefully underpowered rental car around on the side of Cotopaxi, been extorted at a toll road in Mexico, and spent part of a trip in a French emergency room.

The kids rolled with an astonishing amount of it, and for years, I figured if we could make something work, why not? These days, I still know we could handle most of those things. I’m just less interested in finding out.

 

I Don’t Automatically Book the Cheapest Award Anymore

 

This might be the biggest change in how I use points and miles. Back then, if one flight cost 30,000 miles and another cost 50,000, I wanted the 30,000-mile flight. Never mind that it had two connections, left at an ungodly hour, or cost us most of a day at our destination—I was saving 20,000 miles!

The funny thing is that points felt almost endless back then. Huge welcome bonuses were easier to come by, and another big stash of rewards never seemed very far away. Yet I was far more reluctant to spend them.

They’re harder for me to come by now, but I’m much more willing to pay extra for a nonstop flight, a better departure time, or an itinerary that doesn’t make me tired just looking at it.

That doesn’t mean I don’t care about getting a good deal. I’m still going to search multiple programs, compare my options, and die a little inside when an award costs more than I want it to. But when you’re booking for five people, the inconvenience gets multiplied by five, too. Sometimes spending another 50,000 miles means everyone gets a full night’s sleep and we gain another day at our destination. I’m much better at factoring that into the price now.

 

I Care More About Where We Stay

 

 

My hotel strategy has changed quite a bit, too, although some of that is just the reality of traveling with much bigger humans. When my kids were little, my standards were pretty simple: Could we all fit, and was it cheap? Tiny vacation rentals were often perfect for us, especially on longer trips. Give me a kitchen, a washing machine and enough places for everyone to sleep (or even just a big floor), and I was happy.

Four little kids can also squeeze into spaces that four teenagers and young adults absolutely cannot. But these days, occupancy limits matter more. Bed configurations also matter. And we need at least two rooms, which can quickly turn a hotel that looks like a bargain on points into a very expensive redemption.

Other hotel benefits have become more valuable as the kids have gotten older. Complimentary breakfast is a perfect example. Feeding an 18-month-old at breakfast isn’t exactly a major expense. Feeding several teenagers with endless pits for stomachs every morning on vacation is a completely different situation.

I’m more willing to use extra points or cash for enough space now, and I pay more attention to benefits such as breakfast, lounge access, and suite upgrades when deciding where we’ll stay.

 

I Stopped Letting a Good Redemption Dictate the Trip

 

 

I also used to have a tendency to find a great redemption and then build the trip around it. In 2019, I transferred 100,000 Ultimate Rewards® points to World of Hyatt for five nights at the Andaz Costa Rica Resort at Peninsula Papagayo. At 20,000 points per night, it was a fantastic deal, and the resort itself was beautiful. But it wasn’t necessarily the best fit for us.

We felt somewhat trapped at the resort; food was expensive, and getting around Costa Rica without a rental car was a pain. I ended up spending around $1,000 on transportation during that trip, which still hurts a little to type all these years later.

Then we left the fancy points hotel and went to a little hostel in Tamarindo. Breakfast was included; we met up with friends, and my older boys learned to surf. It was much more our speed.

I still love a great hotel redemption, but I’m better about asking myself whether I actually want to stay at the hotel before getting excited about how many cents per point I’m getting. The same goes for flights. A great sweet spot isn’t particularly useful if it gives us a trip we don’t really want.

 

Traveling Got Easier, but Scheduling It Got Harder

 

 

There are a lot of things I miss about traveling with little kids, but hauling an 18-month-old through an airport isn’t one of them.

My kids know how to travel now. They carry their own bags, know how airport security works, can entertain themselves on long flights, and don’t need me orchestrating every second of a travel day. Ironically, they’re now far better equipped to handle all those terrible itineraries I used to book. The problem nowadays is getting everyone on the trip in the first place.

Little kids may require an enormous amount of physical work, but they don’t have jobs, packed school schedules, sports, activities, or many opinions about when you’d like to leave for Guatemala. That flexibility was incredibly useful for award travel. If the cheapest awards left on a Tuesday, we could leave Tuesday. If staying another few days saved a pile of miles, we’d stay.

That’s much harder now, and it’s another reason I’m more willing to spend extra points for the flight that actually works. When you only have a certain number of days together, burning one of them on a terrible itinerary doesn’t feel like nearly as good of a deal.

 

The Best Parts Usually Had Nothing To Do With Points

For all the stories we tell now about Machu Picchu, volcanoes, bungee jumping, and the Sahara, a lot of those years were surprisingly ordinary. We went grocery shopping. We ate an embarrassing amount of fast food. We had rainy days, lazy days and days when I had absolutely nothing planned. We weren’t always “vacationing” so much as doing our regular family life somewhere else.

On one trip to Guatemala, my kids met another family at our hotel pool. Their five kids were almost exactly the same ages as mine, and they became instant friends. For the next several days, we explored together, visited a chocolate factory, ate pupusas, and put on talent shows when the weather kept us inside.

Those are the things I tend to remember—not whether I got 1.7 or 2.3 cents per point on the hotel nights.

Related: How I’m Planning a Six-Week Europe Trip With Kids Using Points and Miles

 

Bottom Line

I’m still cheap, and I probably always will be. But after 10 years of doing this, I’ve gotten much better at knowing when spending more points is worth it.

I wouldn’t book a lot of the trips today the way I booked them back then, but I’m also not sure we’d have seen half the world if I hadn’t been so determined to stretch every point and make every ridiculous itinerary work. These days, points are harder to come by and getting everyone together is harder, too. I’m happy to spend a little more of one if it helps us use the other better.

 

 

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