From Sea to Shining Sea: How and Why We Traveled All Summer

Aug 13, 2019

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And just like that, summer is over.

I know the season still has some life left in it if you live up north where Labor Day marks the end of summer or if you measure the season solely by the heat index (over 100 degrees here in Texas, in case you’re curious). However, for many in the country, the school buses are already rolling, ending our days of family freedom.

Admittedly, summer with young kids is hard for working parents, and there were days I wished for its anticlimactic end and a return to structure and routine, but I’ve been a parent long enough now to know that summer is fleeting, even when the days feel long.

My approach to a family summer vacation has always been to start early, ride it hard and don’t stop until you absolutely have to. As usual, we left for our first trip the day after school ended. Last night, we flew back into town the night before the first official back-to-school event. I’m totally and utterly exhausted, but we used every shred of the long, warm days that were available to us and here’s why.

Related: Best Credit Cards for Families

You Only Get 18, Less Really

Simple math tells you that the number of summers spent with your kids is finite. You only get 18 summers with your kids while they are kids, but it’s really less than that since summer doesn’t mean the same thing for those who aren’t in school. Then, once your kids creep into the teenage years, their summers are likely not totally free.

She
She’s already growing up fast. (Photo by Summer Hull / The Points Guy)

If I only get 12 to 18 of something — ever — I want to make each one count, which for us means hitting the sky, sea, rails or open road in search of adventure. Do as much as we can, for as long as we can. Yes, we factor in pool time at home too, but I’m not about to burn a whole summer just working on our tans in the neighborhood pool.

Looking Beyond Your Own Backyard

My daughters’ day-to-day community is, in some ways, pretty homogeneous. We live in an East Texas suburb lined with Target, Chick-fil-A, banks, churches, SUVs and pine trees. It’s a fine place to be a kid, ride bikes and go to public school, but I want my girls to see well beyond the streets of their neighborhood. Traveling isn’t the only way to do that, but it’s my way.

At home in Manhattan or suburbia. (Photo by Summer Hull / The Points Guy)

Yes, we had plenty of resort-style fun on our summer trips, but we also saw life beyond East Texas. From the economic extremes of life in California, to small farms on the Big Island of Hawaii, to laid-back life on the North Shore of Kauai and the bustling streets and subways of Manhattan, the people, places, faces, food, sights, sounds and even smells of where we spent much of the summer are noticeably different than at home. That wasn’t an accident.

As I said on a recent Instagram post, the best way (I know of) to teach my children to embrace diversity is to not have just one spot on the planet that feels like home, but to have many places you love and care about. Seeing the ways we are all different, and yet the same, with young, impressionable eyes is worth all of the miles, dollars and missed sleep we cashed in over the last few months.

(Summer Hull / The Points Guy)
(Photo by Summer Hull / The Points Guy)

One-on-One Time

Whether it was on long flights, car rides, walks on the beach or nights in the hotel room together at the end of a busy day, we had a lot of quality together time away from home this summer as a family. Specifically, we had some conversations we normally don’t get to have during the school year. I like to think of it a chance to recalibrate the next chapter of life together as one child is suddenly a legitimate tween and the younger one is officially entering “big kid” territory in pre-K.

Photo by Kim Ebert / The Points Guy
Photo by Kim Ebert / The Points Guy

Family

During the summer months, we had brunch with cousins who live in California, hiked a Hawaiian volcano with my parents, saw the Statue of Liberty with my aunt and her 11-year-old grandson, enjoyed a slumber party in a Times Square hotel with another set of grandparents and cousins (shown below) and got to meet up with friends along the way. We live in a global world, and the people we care about simply aren’t all located in one spot. You can choose to have those who live far away just be photos on Facebook or a FaceTime presence at your table, or you can go take photos together and log some true face time in person.

Family from three states together for 24 hours in NYC. (Photo by Summer Hull / The Points Guy)

Of course, that’s something that you can do year-round, but it’s often easier to get families with kids together in the summer when many people have more flexible schedules at the same time. I won’t lie, it has only gotten harder pulling this off as the kids have grown. Some visits were more brief than in previous years, but we got it done because we’re simply too stubborn not to. Like working out or eating healthy, it’s much harder to restart the tradition of getting family together, once it stops, than it is to keep it going.

How We Got Around

From memory, from June 1 to August 11, my girls flew about 14,000 miles on around 11 different flights on six different domestic airlines (if I’m not forgetting anything). There were some shorter road trips, too, but this was a domestic-focused summer where we explored from sea to shining sea with little preference given to any specific chain or alliance.

The girls’ summer (Image courtesy of the Great Circle Mapper)

It wasn’t all paid for with miles and points, but a lot of it was. On the rest, we earned as many awards as possible to use next time around. Here’s a full play-by-play of how we booked three weeks in Hawaii. In that breakdown you’ll find island-hopper flights for 2,100 Southwest Rapid Rewards flights, the Sheraton Kona using Marriott cash and points, the Grand Hyatt Kauai for 25,000 Hyatt points, a room near the airport in Seattle for 38,000 Radisson Rewards and a cabin on a volcano for about $100.

(Summer Hull / The Points Guy)
(Photo by Summer Hull / The Points Guy)

To make a July Disney “camping” trip a reality, we turned to a Kids Fly Free offer on Frontier Airlines and jumped on heavily discounted rooms at Disney World that brought the price of an entire cabin for up to six people down to just $240 per night (maybe this is why that was possible). When a parent and child can fly from Houston to Orlando for just $26 total each way, the list of reasons to stay home shortens in a hurry.

(Photo by Melissa Ann Photography for The Points Guy)
Horseback riding at Disney World. (Photo by Melissa Ann Photography for The Points Guy)

Rounding off the summer in Manhattan with extended family meant piecing together a few stays from at least three different points programs. Not only did we spend 15,000 Wyndham Rewards points to put all four cousins and grandparents in a family suite for a slumber party in Midtown (now 30k points per night), but we used the heck out of our Marriott 35k award nights from cards such as the Marriott Bonvoy Business™ American Express® Card and Marriott Bonvoy Boundless Credit Card at the Fairfield Inn and Suites Manhattan Times Square and the AC Hotel New York Times Square.

For the record, the AC is a new points-friendly favorite of mine in NYC. (Here are lots of Marriott 35k options in NYC.)

AC Hotel Times Square (Summer Hull / The Points Guy)
AC Hotel Times Square (Photo by Summer Hull / The Points Guy)

Bottom Line

It’s fair to say we all now need a vacation from our summer vacation. That 6:30am alarm that signals the start of school will hurt as it buzzes for the first time in months, but as we shuffle our way into fourth grade and pre-K, we’ll look back on our summer knowing we made the absolute most of it. Living life on the go wasn’t always easy, cheap or necessarily restful, but summer is the time of year that our kids are actually ours to mold for more than just a few days at a time. One of our goals is to mold them into being citizens of the world and not just residents of their own backyard. By that measure, the summer was a resounding A+.

While the sun on this summer is setting, it is the perfect time to start planning for next year by pouncing on welcome bonuses of 100,000 points or more and reading up on some especially magical family-travel destinations. As for us, next summer you’re likely to find us collecting a number of passport stamps, if all goes as planned, so we’re going to need all the miles we can get.

I’d love to hear how your family squeezes as much as possible out of the summer.

Photos by author except as indicated.

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