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A Family Afar: A Parent's Guide to Scrappy Vacation Planning

Four pointers to plan a vacation around your high-schooler's schedule


Illustration by Daniel Zalkus

As our girls have grown into teens with their own tastes and actual opinions, traveling has gotten harder. They don’t always want to leave their friends, or miss the big game, or visit a place that is too hot, too cold, or too boring.

One of the biggest issues is scheduling around the school calendar. When they were little, it was easy for Sophia and Ava to miss elementary school. In fact, their teachers encouraged our travel. They knew the girls would learn a lot from being exposed to real-life history, artifacts, customs, and cultures. They recognized that touring the Roman Colosseum or the Tower of London in real life would be a far richer experience than reading about them in a book. Their teachers sent us off with their blessings and a notebook, alongside a request that each girl bring back a travel diary of their adventures to share with the class.

Later on, in middle school, the lessons became more difficult and so did the teachers. In order to take a trip during the school year, we’d have to sign a contract stating we would ensure the girls did their class assignments while traveling. Now, in high school, missing class is really not a great option. Too much content is covered each day, it has proven very hard for them to catch up, and there’s added pressure not to miss sports practice.

Traveling as a family has now become a catch-as-catch-can situation, constantly shifting along with school and work schedules. Instead of planning our trips far in advance, we wait to see about team competitions, important social events, and project due dates. This last-minute approach requires some scrappy budget management and spontaneity to pull off a vacation for four, but thankfully we’ve found creative ways to work through these challenges and have a few tips to share on that front:

1) It pays to participate in points programs like Hilton Honors or Marriott Rewards. If you’ve reached a certain level, these programs can make it easier to request upgrades or booking changes. As a Hilton Honors Diamond member (which requires 30 stays in a calendar year; fewer for Silver and Gold memberships), we’ve received automatic room upgrades at no extra cost at check-in for any property in the Hilton Hotels family, including most recently in Santa Barbara.

2) Choose one or two airlines you can tolerate, then go all in. Many years ago, I chose to use American Airlines exclusively and it has paid off. Miles add up fast, and we’ve found great deals within a few weeks of flying out—especially if we are okay sitting separately. I also recommend the “credit card roulette” trick (just remember to watch the fine print), because most cards offer a big bonus for signing up—up to 200,000 at certain times of the year!

3) Wait until the bitter end to book, like a few days before you’re traveling. This tactic isn’t for the faint of heart, but it can be successful. Often hotels and airlines will heavily discount unsold inventory as the dates approach, because they lose money on rooms and seats they don’t fill. Sites like The Points Guy, Expedia, and Skyscanner help track these fares. We had good luck in San Francisco doing just that, and paid about 30 percent less on the room rate.

4) Be flexible on the destination, and ready to jump. Bargains pop up all the time, and perhaps you never knew you really wanted to visit Timbuktu. We’ve had the best experiences with this by flying out of Tijuana via the Cross Border Xpress. Fares are much lower than at SAN, to destinations throughout Mexico. We once ended up in Huatulco, a beach resort town off the beaten path in the state of Oaxaca—just another case of Dad’s spontaneity turned into family memories.

Jon Bailey writes the travel blog 2dadswithbaggage.com. 2DadsWBaggage 2dadswithbaggage

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