Passports and Eyerolls

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I Had a Plan

To even begin to frame the planning logistics of a trip like this, a little history and context feels necessary.

I always intended to travel as an adult. I earned a Master’s in Global Health Policy with every expectation that I would leverage my shiny new credentials into a globe-trotting career with the WHO, the IMF, or some nonprofit that would allow me to greedily collect stamps on my passport. Marriage? Family? Pffft. I would be the eccentric aunt who breezed home for the holidays bearing gifts children wouldn’t fully appreciate until their twenties.

“That? Oh, my aunt brought that back from Laos one Christmas. Isn’t it lovely? Where is she now? Nepal? Mongolia? Who knows!”

I had a plan.

Then I ran into a problem. A 6’2”, funny guy from Buffalo, New York. And I fell in love.

Dan worked in construction, and when, what we both assumed was a summer fling became something more, I optimistically thought, “Buildings… construction… they build things everywhere. We can make this work.” But as the years passed – marriage, kids, careers – it became clear that Dan was, at his core, a homebody. He enjoyed travel in short bursts, but the idea of leaving the U.S. long-term held no appeal. He loved his job, his company, mowing the lawn, Sunday football, and being close (by American standards) to family. Packing up and living abroad was simply not his dream.

It very much remained mine.

Having children didn’t change that. If anything, it intensified it. I wanted my kids to experience the kind of exposure to the world I had growing up.

When Dreams and Love Collide

So. Impasse.

And what do you do when you hit an impasse in a loving, long-term relationship? You talk. You fight. You talk some more. Eventually, you compromise.

Our compromise: the boys and I would travel round the world for seven months. Dan would stay behind and join us when his job and schedule allowed. Another major part of that compromise was waiting until we’d saved enough money to feel cautiously comfortable that the trip wouldn’t completely decimate our finances.

In case it isn’t obvious: I’m firmly in the “YOLO, we’ll figure it out as we go” camp. Dan lives squarely in the “I would prefer not to bankrupt us in the process” camp. This is why our marriage works.

The Budget: Buzzkill and Best Friend

Creating Parameters (a.k.a. Crushing Dreams…Gently)

If you’re anything like me, you look at a world map and think, “Yep. All of this.” Then your (very real) budget metaphorically smacks you on the nose with a (metaphorical) rolled-up newspaper (still stings though) so you open a spreadsheet, and you get practical.

One of the driving motivations for this trip was to expose my children to the world, so (benevolent mother that I am) I asked where they wanted to go. Mistake. Italy and Japan topped the list, followed closely by France and Dubai. The budget quickly crushed those dreams, though oddly this was somehow blamed on me.

Lesson learned: involvement is great, but parameters are essential.

First: we would avoid cold weather. This decision was driven almost entirely by packing logistics (see the packing post for details).

Second: while Australia and New Zealand were tempting, they were simply too far-flung for the time we had. Some places just weren’t going to make the cut.

“Limited time?” you may ask. “Andrea, you’re traveling for seven months!”

Yes, it’s a longtime but also…not.

Which leads to parameter three: most long-term travelers will tell you the best way to immerse yourself in a place—and save money—is to slow travel. A month or more in one country, really settling in. For us, however, the goal was breadth as well as depth. We wanted to see as much as possible in the time available, which made spending a month in Australia impractical (at least…for this trip).

Finally, time and budget permitting, I wanted a mix of education, immersion, and a few fun, budget-stretching splurges, particularly for the teens. There will be grumbles and eyerolls, this is inevitable with our without trave, but I wanted moments that felt special to them.

Building the Route: Anchors, Requests and Splurges

With those parameters in place, a plan slowly emerged. Since we were starting in January, we’d begin with a long-haul flight to Southeast Asia and then meander west, loosely following warmer weather.

The tween request was to experience New Year’s Eve in Singapore, so that became our first stop. Dan would join us there, and since he is decidedly not the backpacking type, Singapore became one of our splurge moments (which, frankly, Singapore excels at anyway).

The teen requested mountains, so Nepal and Bhutan made the list. I have family in the Netherlands that my kids have never met, so that became another anchor point.

Then came research. While this trip feels big and groundbreaking for us, long-term family travel, RTW trips, gap years, extended travel – call it what you will – is not a new phenomenon. I am deeply grateful to the travelers who documented their experiences and shared tips, tricks, and inspiration. I’ve linked many of them on my research page; their adventures are well worth exploring.

As the outline solidified, I learned another important lesson: it’s okay to ask for help.

I love trip planning and consider myself quite competent at it. I’ve planned countless family trips and helped friends do the same. But India—one country I knew I wanted to include—gave me pause. I lived there as a child, and it’s magical, complex, and endlessly fascinating. It’s also intimidating to plan once you venture beyond the “Golden Triangle.”

So, for the first time ever, I contacted a travel agent. Geraldine Hastings of Virtuoso Travel came highly recommended by my brother and his fiancée, and I’m happy to pass along that recommendation. When I described our plan and budget, she barely blinked (okay, maybe she blinked once) and immediately began crafting an itinerary that balanced history, culture, and experiences that would engage two teens. She recommended places I hadn’t even considered.

It was a good reminder that you don’t have to do everything yourself. If you’re daydreaming about a destination but feel overwhelmed by the planning, there are professionals who can help make it happen.

The Glorious Expanding Spreadsheet Phase

Speaking of spreadsheets: it was time.

I love a good spreadsheet. Watching dates and destinations line up neatly is a very specific dopamine hit. I created tabs for:

• General trip overview
• Detailed itinerary
• Budget and spending tracker
• To-do lists
• Transportation, accommodations, and activity research
• Packing lists

As the workbook ballooned into hundreds of rows, I once again sought help, this time with organization. I discovered Smart Women Society’s Ultimate Travel Planner, which quickly became the trip bible. With intuitive tabs and built-in formulas, it allowed me to track bookings, spending, packing, and logistics all in one place (and it’s pretty!).

Still looming on the to-do list: what to do about the boys’ schooling, and what to do about my own career. Both deserve posts of their own.

The Moment

Finally, it was time to start booking; to turn theory into reality. The first bookings were for Singapore and hitting “confirm” on those flights (while mentally hearing the ka-ching of our savings taking a hit) was one of the most surreal moments of my life.

Something years in the making had officially begun.