12 Lessons We Have Learned About Traveling With the Family in Summer
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We're writing this from somewhere in the middle of our Euro summer. Every year we think we have this figured out. Every year the trip corrects us on something.
So here are twelve. Not rules, because rules imply we follow them consistently. Lessons, because we learned them by getting them wrong first. They run in rough order, from long before you leave to the moment you're standing in it.
1. Start planning next summer during this one
We are currently on this summer's trip and Thomas is already looking at summer 2027. That's not a joke. It's the single biggest reason these trips work.
A year out, you get first pick of everything. The flights are at their sanest, the places you actually want are still available, and you're choosing dates instead of taking what's left. Book the same trip in March and you're paying a premium to compromise.
There's a quieter benefit too. A trip you've been looking forward to for a year gets enjoyed twice, once in the planning and once on the ground. The anticipation is not a side effect. It's part of the product.
2. Three to five nights is the sweet spot
Two nights is a travel day, a real day, and another travel day. You never learn where anything is, and you spend the whole stop packing and unpacking. The only version of it that works is the weekend trip in Ireland, launched from Thomas's parents' house, where nothing needs unpacking in the first place.
Three nights is where a stop starts to work. Four or five and you've found your bakery, the boys know their way around, a place starts to feel a little bit yours, and you leave while you still want more of it. That last part matters. Leaving a place slightly too soon is how you end up loving it. Staying a week past the point of curiosity is how a trip starts to feel like a slog.
Enough nights to belong, few enough to still be a guest. Build the itinerary on that rhythm and most of the other decisions get easier.
3. Let the kids decide some of it
Not all of it. Some of it, and genuinely, while the plan is still being drawn.
The difference between a kid who's being dragged and a kid who's along for it is whether he had a say. Give them a real vote on a few days and the whole tenor changes. They stop being cargo. They're invested, because part of the plan is theirs and they want it to work.
It's also how the trip becomes theirs in memory, not just ours. The days they chose are the days they own, and years from now those are the ones they'll bring up unprompted. They also pick things we would never pick, which has been the source of some of the better afternoons we've had.
4. Book the anchor meals before you leave
We plan our trips around dinner and we're not embarrassed about it. Two or three real ones a week, the kind with a room and a menu and an actual reason to be there.
Those book out. Not the day before, not the week before. If it's a place you've been reading about for a year, it wanted your reservation a month ago.
So we do it from the couch at home, before anything else is decided. The rest of the itinerary can arrange itself around them. It usually does, and it's a better itinerary for having something fixed in it.
5. Split the jobs and stop negotiating them
Thomas does logistics. Flights, cars, bookings, the whole timeline. Scott does wardrobe. Nobody consults, nobody second-guesses, nobody relitigates the decision at the airport.
The admin lives inside the same split. Passports checked well ahead, travel insurance, phone plans sorted, the bank told you're going. One person owns it, does it once, and it's done. Four people half-checking whether the passports are valid is how nobody checks.
The driving is divided the same way. Ireland is Thomas's, because we borrow his parents' car and that's the arrangement. Everywhere else is Scott's. Whatever your version of the split, don't let one person do all of it. The driver isn't on vacation the way everyone else is.
Most travel friction between two adults isn't about the decision. It's about who gets to make it. Assign it once and the argument disappears permanently.
6. Build the lookbook
Which brings us to Scott's job, and the system people ask us about most. Before a trip, every outfit gets planned out. Not the clothes. The combinations. Top, bottom, shoes, what it's for, which day.
The point isn't the clothes. It's that you never have to think. You're jet-lagged in a hotel somewhere at 8am and there's a document that says what you're wearing, and you put it on, and you're out the door twenty minutes earlier than you would have been. Every decision you make in advance is one you don't make while tired.
It also means you actually packed for the trip you're on, because the gaps show up while you're still standing in your own closet. One note from experience: leave a little room in the plan, and in the bag, for the things you pick up along the way. Some of the best pieces in the rotation weren't in any lookbook. They were found on the trip, and the trip should get a say.
7. A suitcase per destination, and a photo of what's inside
When we're doing multiple stops, each place gets its own bag. You take the relevant bag out of the pile, you're dressed, and everything else stays closed. It sounds fussy until you've done it once, and then going back to excavating one big bag for a month feels insane.
And before each bag closes: photograph the inside. This one paid for itself this very summer. One of our bags went missing on the way to Portugal, and the photos meant we knew exactly what we were dealing with, both what needed replacing right away and what we'd be claiming with the airline. It showed up in the end, they usually do, but there's a real difference between working from a photo and working from four people's guesses about what was in there.
On a normal trip it earns its keep in smaller ways. You will not remember what you packed. You'll buy a second charger, or spend twenty minutes convinced you left something at home that's in the outside pocket. Two seconds per bag, and the question is answered every time.
8. Pack a carry-on you could live out of for two days
Learned this one in Athens. Our bags didn't make the transfer and we were flying to Santorini with, between the four of us, zero swimsuits. Going to Santorini. In summer. We ended up splitting the problem, one of us taking the boys to buy the essentials, the other going back to the airport to chase the suitcases, and it all worked out, but we spent the first day of that trip solving a problem instead of being on vacation.
So now: two days of clothes for everyone in the carry-on, plus swimsuits, plus anything that would be a genuine problem to replace. Not a token change of shirt. Two functional days.
And within that, a fresh change of clothes reachable on the travel day itself. Drinks get spilled on planes. On children, near children, by children. It has been known to happen. The difference between a ruined travel day and a funny story is one clean t-shirt in the right bag.
9. One cultural thing a day. That's the whole quota.
If we could only hand over one of these twelve, it's this one.
One museum. One castle. One church you climb the tower of. Then you're done, and the rest of the day is for the place itself. The instinct is to pack it in, because you're here and it's expensive and who knows when you'll be back. But six things in a day means you saw none of them and everyone is quietly furious by 3pm.
One thing, and the rest of the day belongs to the place itself. And that part isn't filler. Roaming the streets with nowhere to be is how you actually see somewhere: how the locals live, where they shop, what a Tuesday looks like there. You end up in a neighborhood you didn't research, at a table you didn't book, and that's the day you'll describe when you get home. The museum was the excuse. The wandering was the trip.
10. Downtime in the room is part of the plan
Not slack in the schedule. Not what happens when something falls through. Scheduled, protected, on purpose.
An hour or two back at the room in the afternoon. The boys decompress. We review the day's photos, figure out what we're posting, answer the things that need answering, or do absolutely nothing, which is also a legitimate use of the hour. Then everyone goes back out human again.
Four people in close quarters for weeks need a pressure valve, and it's cheaper to build one in than to deal with what happens without it.
11. Devices aren't the enemy. Used badly, they are.
We're not going to pretend the boys are device-free on a long summer trip. They're not, and the families claiming otherwise are on shorter trips than we are.
But there's a right way. Devices for the flight, for the downtime hour, for the train. Not for the table, not for the walk, not instead of the thing we came here for. And the piece people miss: it's how they stay connected to their friends at home. A whole summer is a long time to be a kid away from your people. A boy who got to talk to his friends for twenty minutes is a boy who's happy to be here for the rest of the day.
Used badly, a device takes them out of the trip. Used well, it's part of what makes a long trip work for them. That's a difference worth managing rather than banning.
12. Some photos are for socials. Some are just for us.
We share a lot of our life online, so this distinction matters more in our house than most.
There are the spots we shoot for the feed. Planned, done properly, and done first so it's out of the way. And then there are the photos that will never be posted anywhere. Not because they're bad. Because they're ours.
We say it out loud when we're shooting, to the boys and to each other. "This one's just for us." It keeps the line clear for everyone: some of this is content, and most of it is simply our life. The just-for-us folder is the one we actually sit and go through in December, and it's better for never having had an audience in mind.
If your whole camera roll is for other people, none of it is for you. Decide which is which before you lift the phone, and say so to the people in the frame.
The trip they remember is never the one you planned. Ask the boys about any summer and you won't get the castle. You'll get something small and sideways that we had no part in arranging.
You can't build that. You can only leave room for it, which is what most of the twelve above are really for. Fewer plans, more hours, less packed in. Then get out of the way.
If you've got one we've missed, tell us. We're still learning them!
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