When my kids were tiny babies, I remember having a conversation with a girlfriend who had two children herself. They were getting ready for their annual Cabo getaway.
I thought it was strange at the time that a family would have vacation time and choose to spend it in a place they had already visited so many times. Weren’t vacations supposed to be about going somewhere new? Seeing something different? Having an adventure?
But when I listened to her story, I understood. Her boys knew the area, the hotels, the restaurants, and what they wanted to do. Most importantly, the whole family looked forward to that trip with immense pleasure.
I remember thinking, What a great idea—to have a place that a family could call their vacation getaway.
As it turns out, we eventually fell into a couple of our own.
We found our first one quite by accident when I had an event in Phoenix, Arizona, the city where I grew up. We took the whole family and stayed at a beautiful resort I remembered from my teenage years: Hilton Phoenix Tapatio Cliffs Resort.
When I was a kid, I remember it as an exclusive resort tucked into the side of North Mountain Park, with beautiful views of the city lights and fabulous Southwest architecture.
We stayed there because another hotel reservation fell through—and I am so glad it did.
What I didn’t know was that this beautiful resort, which I remembered mostly for proms, weddings, and big executive events, was also an amazing water-park resort.
We started going when our kids were just three and four years old. Throughout their childhood, we would return every year for four or five days in the sun.
Growing up in Colorado, this was paradise for my children.
The hotel had a number of pools—I think we counted eight total, although the resort now lists seven—and from our first stay, we affectionately called it our pool hotel.
And the name stuck.
The best part was watching my kids grow up knowing the resort and Phoenix so well that they eventually felt like it was another hometown.
There is something incredibly comforting about pulling under the porte cochère at the entrance to that magnificent lobby. Just arriving felt like exhaling. We were on vacation, everyone knew where we were, and nobody needed a complicated itinerary.
For a parent, that is basically a luxury vacation all by itself.
Our second repeat getaway came a little later when we started heading to Vail, Colorado, every Labor Day.
We stumbled into this tradition quite by accident too.
Over Labor Day weekend, Vail Village used to host a fabulous food and wine festival, where restaurants from Vail, Avon, and the surrounding communities came together for an open-air food and wine fest.
Vail in late summer is pretty magical. The air is crisp and just starting to turn. There’s no skiing, obviously, but the village feels like something plucked straight out of the Swiss Alps.
There’s also the Vail Jazz Festival over Labor Day weekend, and the music is fantastic. The festival is still going strong today, with the 2026 event scheduled for September 4–6.
Because we lived in Colorado Springs, the trip to Vail was only a few hours. After a long, sweltering Colorado summer, that cool mountain air was a welcome relief.
And then there was the real magic of both of these getaways.
Because my kids knew these places so well, they would eagerly leap out of the car when we arrived. Sometimes I barely saw them for the entire weekend. They were off exploring, swimming, playing, and generally doing whatever kids do when they realize their parents aren’t hovering over them every second.
And I was okay with it.
The familiarity gave them a sense of independence while they were still close to their family. They knew where they were. They knew how things worked. They knew where to go.
They weren’t bored by the repetition.
They loved it.
Sometimes we think a family trip will be fun for the kids, but they are actually dreading it. I believe Chevy Chase made a movie or two about this very phenomenon.
You know the drill: Mom and Dad are thrilled about the “family adventure,” while the kids are silently wondering how many more hours they have to spend trapped in a car.
Repetitive vacations can solve some of that.
I highly encourage young parents to find a spot that they can easily and inexpensively commit to for years. Some people choose a timeshare. That can be great if you are a fan of timeshares.
I liked that neither of our getaways was incredibly expensive.
Our pool hotel was exceptionally affordable because Phoenix in the summertime is practically giving away hotel rooms. But when you live in Colorado and spend much of the year dreaming about warmer weather, hot is excellent for a week or so.
There is another benefit to choosing a familiar place: you don’t feel the pressure to see and do everything.
When you visit somewhere for the first time, there can be a slightly frantic feeling that you have to maximize every minute. You need to see this attraction! Try that restaurant! Drive over there! Wait—did we already pass that thing?
With a repeat vacation, you can relax.
You already know where the good stuff is. You know what you like. You know what you can skip. And if you don’t make it to something this year, there is always next year.
That, my friends, is a beautiful thing.
Vacations don’t always have to be exotic or remote. They don’t have to involve a passport, twelve hours of flying, and a spreadsheet that would make a corporate project manager nervous.
Family vacations should be something fun for everyone—and especially something your children love and look forward to.
Sometimes the best vacation tradition isn’t seeing somewhere new.
Sometimes it’s going back to the place where everyone already knows exactly how to have fun.
