The Best Family Vacation I Ever Took

When you're planning a trip with your kids, what you really want to know is: What have other people done that's been awesome? And can I copy it? Four writers share some simple revelations that changed everything.

5 min

We went back to our roots.


Last year, thanks to Zika and several family members trying to get pregnant, the Thanksgiving vacation my extended family had been taking to Mexico for a decade required a new location. We needed warm weather, nonstop flights (for 16 people, from both coasts), and no mosquitoes. Our options were thin. But my mom had an idea: Rent a house in Scottsdale, Arizona, where we four kids grew up. Since my parents abandoned my hometown for San Francisco 12 years ago, I'd been back only once, for a day. Scottsdale held zero interest for me. But a consensus among family is hard to achieve, so while a broker friend found us a five-bedroom with a pool, I packed my hiking boots and kept expectations low.

Oh, I was so wrong. A multigenerational trip with lots of competing goals can actually work pretty well when you're all under one roof in a place you know by heart. We could explore all together, like when we schlepped up to Saguaro Lake to motor through the narrow reservoir—the ideal moment to retell the story of the day I skipped class, stole a boat, and accidentally sank it. We could split up; one day, half of us peeled off to hike some stunningly desolate canyon with my older sister's high school besties. And we could have a Tuesday-night dance party in the huge living room, with my 11-year-old son DJ'ing. Having a kitchen was key; my brother-in-law made huevos rancheros daily for breakfast (and manhattans for grown-ups at 5 p.m.). My mom brilliantly sourced a catering company that grocery-shopped, then came one day and prepared three reheatable dinners, taking some of the pressure off cooking a zillion meals in one week (or arguing about where to go out).

Rather than being bored in the site of their parents' awful suburban youth, our kids were hypnotized by the ancient cacti, the cave-size holes in the rocks of Papago Park, and the vast emptiness of the desert, so dramatically different from anything they'd experienced anywhere—even Mexico. Neighbors I hadn't seen since graduation popped by. Unlikely groups organically formed and ventured out to grab cocktails at the historic Biltmore hotel, climb towering Pinnacle Peak (you go, Dad!), or visit Frank Lloyd Wright's Taliesin West studio. There was no schedule, no required attendance, and, bizarrely, no reverting to our horrible teenage selves—perhaps since very little was asked of us other than to have a good time and be home for dinner.

I have 192 photos from that week on my iPhone, more than from any of our past full-family trips. Viewed together, they reframe the lackluster setting of my childhood as a place filled with adventure and serendipity. Revisiting a town I know so well relieved the urge to cram every attraction into one week. Staying together in a house, rather than scattered across a resort, somehow made me feel like I had the luxury of space and time. To go for a beer run with my brother, to play games with my nephew, or to just read by the pool with my new sister-in-law. Months later, I still have the glowing texts from my dad: "Out now with boys doing nature. No obligation. I love every second."

We embraced the kids' club—guilt-free.


It's a truth universally acknowledged that a mother on vacation with family is just a mother doing her job in a new (lovelier) location. Feeding, bathing, entertaining—the basic needs don't evaporate just because you're in a new time zone. And that's the cruelty of it all. You've traveled to a spot where doing those daily duties feels even more onerous than usual. After all, that hammock has your name on it, and what's the good of bringing a beach read if you never get to the actual reading part?

The answer, of course, lies in two of the most beautiful words in the English language: kids' club. Variation: Kidz Klub. Definition: the entity that turns a trip into a vacation.

Until a few years ago, my husband and I had never stayed anyplace where this was even an option. Either the hotel wasn't full-on resorty enough to have a kids' program or our kids weren't old enough to be dispatched to their own activities. Yet there we were, dropping our daughter off at Skully's Imagineer Club at South Seas Island Resort on Captiva Island, Florida. We'd looked at the club longingly the first time we visited, a few years back, when we had a toddler (read: too young for Skully's) and another baby on the way. We'd heard from other parents: Go kids' club and you'll never go back. But I'll admit I felt a bit like I was pushing my daughter to walk the plank as we waved goodbye. It somehow seemed worse than a typical date night, since we hadn't already logged a full day with her and certainly didn't know these babysitters. What if they were pirates?! But as I sat on a lounge chair later, reading over the activity schedule—it had something to do with wacky sports or mad scientists, I believe—that guilt melted away like a frozen daiquiri in the Florida sun.

And it's not like we were totally free to just hammock it up for the morning. Our younger daughter wasn't old enough to be dropped off. But having even half the load lifted felt intoxicating. (Although maybe that was the daiquiri.)

Each day while my older daughter was off exploring, making art projects, and burning off a ton of energy, my husband and I took turns with the younger one in the kiddie pool or on the resort's free trolley, always a huge hit. We had precious alone time with our second-born—time when she didn't have to race to keep up with her big sister or compete for attention. It also meant that one of us could be completely off-duty without feeling like the other was outnumbered. And let's be honest: Couple time is lovely and all, but those hours by myself were glorious. I actually read that book I packed—at least until I fell asleep 20 pages in. If it was nap time for the toddler, one of us could stay in the hotel room with her while the other went for a leisurely jog. And best of all, when we went back to Skully's to gather up Big Sister, we were refreshed and happy to be a family of four again.

We're going back to South Seas this spring, and for the first time, both kids can skip into Skully's. I expect to get through at least 30 (!) pages of my book before I doze off.

We tacked a vacation onto a family wedding.


When our kids were young, my husband and I took them on plenty of memorable vacations—to northern Michigan, upstate New York, Rocky Mountain National Park, the Badlands, England's Lake District, and Ireland's County Cork. Then we became empty nesters, and the family trips stopped. Our kids were young adults with their own zip codes, lives, commitments, and ideas of fun. Gone were the days when we had control: "OK, kids, hop in the van! Off we go!"

But last June, the six of us—our son and daughter, plus my stepdaughter and her new husband—gathered in Jackson Hole, Wyoming, a result of advanced diplomatic skills, detailed consultations, and a little nudging. I started by nonchalantly making the case that a family vacation kinda made sense, since we were already trekking to Jackson Hole for my cousin's destination wedding. Why not add a "just us" trip? Then my husband and I sweetened the deal by offering to foot much of the bill, especially for our 20-something son and daughter, so everyone could afford to come.

We were careful to get the kids' input, reserving the bossy-parent card for crucial things, like making the final call on a cozy Airbnb cottage with a view of the Tetons. Yes, we had many group e-mails about syncing up flights, but major details (general dates, for example) were already determined by the wedding, which gave us more time to discuss the fun stuff.

And that's where the benefit of traveling with adult children comes in: I could step back from my usual trip planner/tour guide role because the kids stepped up. Cooking breakfast and dinner became a group activity, which is how I found myself learning to make grilled kale. Our son-in-law turned out to be the kind of traveler everyone wants on a group trip. Enthusiastic and curious, he'd done his Jackson Hole homework and suggested what ended up being our favorite hike in Grand Teton National Park. It also produced a new favorite family tale: the one where we set off on a gorgeous trail but left all our water in the car.

Although we came up with a general game plan each morning, we were not overly ambitious, and attendance was optional. We typically wound up together—but not always. And that was fine. The cottage was affordable (paying for everyone's separate hotel rooms would have been less so). And while there was spectacular scenery, wildlife viewing, and cookouts, what I loved most was being able to do something I no longer take for granted: hang out as a family. We had the rare opportunity to catch up and relax in this stage of family life. It was a trip that felt different, almost more special, than the cherished trips we'd taken when our children were little. And on one of our lunches out, the kids even picked up the tab.

We just…went (even with twin toddlers).


Before I got pregnant, whenever I envisioned traveling as a parent, I would picture myself wearing a baby and walking along a hilltop overlooking the Pacific. Or speeding through the Alps on a train while the baby quietly gurgled and my partner and I enjoyed the view. My very first ultrasound put an end to that. Two white blobs in two black sacs. I didn't need the doctor to announce "Twins!" to clearly see that my plans of whiling away a Sunday afternoon in a London gastropub while the baby fell asleep next to me were dust. In that moment, I think I decided subconsciously we were never going anywhere again. And apart from a couple of obligatory flights to see family when the girls were newborns, we really didn't for two years.

But the summer the twins turned 2, one of my best friends invited us to stay with her in Washington, D.C. A car trip from our home in New York—no airfare, no TSA lines—seemed like a doable first family vacation, so we packed up the car with 85 percent of everything we owned and drove down to D.C. Previously a somewhat haphazard packer, I turned into Mama General Eisenhower with D-day–type lists: two Pack "n Plays, sheets for said Pack "n Plays, 32,000 diapers, sippy cups with the hard spout, sippy cups with the soft spout, at least three changes of clothes per day per twin, so much sunscreen. When we pulled up to my friend's house and unloaded everything into her large, finished basement, I felt like the circus had come to town, but I also felt…happy.

It took getting out of my house (and my own head) to realize that the fears that kept us from going anywhere—how they would ever sleep in a strange place or survive without the right kind of mac and cheese—were vastly overblown. Who's completely prepared for a week away with two 2-year-olds anyway? No packing list can prevent nap strikes and public tantrums. It also can't ensure idyllic memories: the joy of swimming in a pool or seeing a horse for the first time. Those happen even without the right mac and cheese. You just have to snap those car seats in and head out.

After a few days at my friend's house, we drove to a resort on the Chesapeake Bay. I wasn't ready to spend an entire week at a hotel (see: sleeping in strange places), but since we were already on the road, I thought two nights at the shore would be a great way to end our trip. We rearranged the furniture in the room to cram in the Pack "n Plays and hired a babysitter so we could go out to dinner. (Lesson: That poor sitter had to sit in the dark all night with two sleeping babies and no TV. We've stayed in one-bedroom suites ever since.) "The key to fun is flexibility!" we reminded each other as we read by the light of our iPhones that night.

That trip made us better parents. We improvised, we laughed, we yelled a little bit, and we needed a lot of help from Disney—"Let It Go" was on repeat for hundreds of miles—but we did it. And we knew we could do it again. Without 87 sippy cups.

A few weeks after that trip, my aunt and uncle invited us down to the Jersey Shore. We didn't hesitate. I cut our packing list in half; at the beach, there were no multiple outfits for each twin. Just a swimsuit plus boxes on their heads while they played robot with their cousin. And, yeah, still so much sunscreen.