How We Decide Where to Go Next

My husband reads faster than I do. I've known this for years, and it's never mattered less than the moment it almost ruined the best surprise of our wedding.

We were reviewing our vows a couple of months before the ceremony. Annemarie, our wedding officiant, had sent them over early so we could read through them. He got there first. I watched him stop, look up, and say: "Huh… Annemarie has planned our vacations for the next twenty-five years."

I had no idea what he was talking about. I told him so.

"Keep reading," he said.

A few minutes later, I understood.

Annemarie had a philosophy: every couple she married should leave the ceremony with something tangible, a memento of the commitment they were making. After we filled out her pre-wedding questionnaire (the kind that asks who you actually are as people, not just what flavor of cake you want), she found the right thing for us. She almost always did.

Buried in our vows was a description of a keepsake box containing twenty-five sealed envelopes. Each one held a destination. On every anniversary, we'd draw one - and that would be where we went that year.

I couldn't think of a better way to celebrate our anniversaries every year.

In the weeks before the wedding, we sat down with maps and way too much enthusiasm and built our list. It was supposed to be twenty-five destinations. We ended up with thirty-two. Some negotiations were swift. Others were not. (Greece almost didn't make it - I'd already been. My husband made a compelling case for going back for the history rather than the hiking. He was right. It's in the box.)

At the ceremony, Annemarie presented the box to our thirty-five guests - none of whom knew it was coming - and invited us to draw the first envelope. I reached in. I opened it. I laughed out loud, not a polite laugh, a real one.

We'd both been quietly assuming Europe. The box had other ideas.

Argentina.

The guests gasped. Then they laughed.

We've been going where the box tells us ever since.

Where the box has taken us (so far):

• Argentina (2011) — Our first draw, and it set the bar high. Iguazu Falls was the standout. We could easily go back.

• Australia (2012) — The Great Barrier Reef was, honestly, a little underwhelming - murky water, not many fish. I'm rooting hard for the reef's recovery and hoping to see it at its best someday.

• Caribbean (2013) — A classic cruise. Relaxing, pleasant, nothing that rocked our world. The box gives you what it gives you.

• Belgium (2014) — Beer and chocolate. I mean, really, what else do you need?

• Morocco (2015) — We weren't sure what to expect. We ended up loving it! The immersion of driving around the country with a guide and driver, going places you'd never find on your own, was exactly the kind of travel we love most.

• Indonesia (2016) — This is the trip we talk about the most. The one that felt genuinely different, special, and unlike anything else we'd done. It's hard to explain without sounding like a brochure, so I'll just say: it earned its reputation in our house.

• France (2017) — Food, food, and more food. The best surprise was Carcassonne, where we stayed in a Best Western that was literally part of the castle walls, and had our best meal of the trip at a tiny restaurant right across the street. Sometimes it really is the unexpected ones.

• Panama (2018) — We were both a little skeptical going in. We were wrong. The day cruise along the canal was fantastic, but the real highlight was our guide - a biologist actively working on the new canal expansion - who gave us a level of insight we never would have gotten otherwise.

• South Africa (2019) — My bucket list item was seeing a rhino in the wild. We saw so many rhinos. We stayed in both Kruger National Park and the adjacent private concessions, which gave us completely different ways of experiencing the same wildlife. One of the best decisions we've ever made.

• Czech Republic (2020) / Peru (2021) — Two Covid cancellations. The envelopes went back in the box. We don't talk about it.

• Egypt & Jordan (2022) — My husband couldn't get enough of the history. I couldn't get enough of the food, which I genuinely did not expect to be a highlight. It was.

• New Zealand (2023) — Breathtaking scenery at every turn. Every. Turn.

• Spain (2024) — Rich history everywhere you look. La Sagrada Família in Barcelona was a standout, and the Alhambra gardens in Granada were something else entirely - the scent was beautiful without being overwhelming, like stepping into a different world.

• Chile / Argentina / Falklands / Uruguay (2025) — Our second lap through South America didn't disappoint. The Falklands were a single day, but they lived up to every expectation I'd brought.

• Norway (2026) — Happening next month. The tickets are booked, the bags are half-packed, and I'm already excited.

And in April, we drew our next destination: India, where we'll head in 2027.

Thirty-two envelopes. Fourteen countries visited (with two we'll always count as the ones that got away). Six continents. One box that has quietly shaped our married life more than almost anything else.

We still go by the same rule we've always had: you go where the box tells you. The bar for putting a destination back is high - genuinely high, not just "I'm not feeling it this year" high. The whole point is to let go of the choosing and just go.

It's the best travel philosophy I've ever had, and I can't take any credit for it. That belongs entirely to Annemarie.

Want to start your own Box Trip?

I've put together a set of printable Box Trip starter kits - you can set one up at home for your own anniversaries, family adventures, or any occasion that deserves a little organized spontaneity. They're in my Etsy shop if you want to take a look.

Kits available: US National Parks, Scenic Road Trips, US States, Natural Wonders, World Landmarks, and Islands.