Getting in the Picture
Capturing the entire family at least once a year gives you the best opportunity to reflect on the trip all year long. Print and hang the images when you return.

Scroll back through a year of our trip photos and you'll notice something quickly: one of us is almost always missing. There's Kyle with the boys on a beach. Me with the boys in front of something tall. The kids, the kids, the kids. But all four of us, actually together in the same frame? Almost never, unless you count a cramped selfie with somebody's arm stretched to the edge of the shot and half a landmark behind us.
It's the oldest problem in family travel. Somebody has to hold the camera, which means somebody is always left out of the picture. We don't travel with a tripod, and we've never been the type to hand a good camera or an unlocked phone to a stranger on the street and hope for the best. So by default, whichever parent is taking the photo quietly disappears from the trip's record.
A few years ago we found the fix, and it has become one of our favorite traditions: once a year, we pick a single trip and hire a professional photographer for an hour or two. We did it first in Costa Rica, then Curaçao, then London.
Finding one is easier than it sounds. Most destinations have photographers who do exactly this, a short vacation or family session. A service called Flytographer has been our easiest way in; it matches travelers with vetted local photographers, and it's how we found both our Curaçao and London sessions. A quick search or a hotel recommendation can turn up someone good too. Whichever route we take, we book before we leave, schedule it early in the trip while everyone is still fresh, and pick a spot that actually means something to that trip rather than the most obvious postcard backdrop.
Here's what surprised me about it. The value isn't the posed portraits, though you get a few of those, the everyone-look-here shots the grandparents love. It's the hour itself. Someone trails a few steps behind you while you just, are a family. The boys run, we chase them, everyone forgets the camera is there, and a stranger with a good eye catches the four of us exactly as we are right now, at these ages, in this place. Those are the photos I cannot stop looking at. Not because they are perfect, but because I am finally in them.
It's a splurge, and it doesn't fit every trip's budget, which is exactly why we cap it at one a year. But of everything we spend on to make a trip special, this is the line item I would cut last. The fancy dinner fades from memory by the time we land. The photos don't.
When we get home, they get a place of honor. We have a wall where we frame that year's shoot and hang it, and it stays up for the rest of the year, the whole family in one spot, together, until next year's photos come to take their place. Our boys are growing up walking past a wall of proof that they were here, that we were all here, at the same time.
They may not remember Costa Rica, or Curaçao, or London. But they will never have to wonder whether we were there with them. It is all on the wall.
- pick one trip a year and book a short session (an hour is plenty) with a local photographer, or through a service like Flytographer that matches you with one
- schedule it early in the trip, at a spot that means something, before everyone is sunburned and worn out
- back home, frame the best few and give them a wall of their own for the year

