We had been talking for days about a move to Europe.

There was a bottle of wine (or two) on the table, and toddler toys were strewn across the floor underneath us and all around. But those had been there for a while, so we poured the wine, finished the last of the homemade pizza, and went on with it: my sister, Hannah, and I were in full-on future-planning, wish-fulfillment mode.

I showed her an Instagram account I’d recently discovered: Cheap Italian Dream Homes (you’re welcome… also, sorry for the rabbit hole you are about to go down).

The feed offers a nonstop stream of dreamy, old-world stone country villas (“to be restored”) with huge old wood doors and arches and views of olive grove-, vineyard-strewn hillsides in places like Umbria and Calabria.

This dream of a cheap Italian villa can be yours for roughly the cost of a down payment on your average single-family home in the suburbs of your average third-tier American city. Well, that and some renovation costs: amount undetermined.

A friendship: Rosa

But I digress. All the talk of Italy got my sister thinking about her friend Rosa.

Rosa is living the dream in Tuscany, in Florence. I knew her as my sister’s friend from various locales, so I know she goes a million miles a minute, a whirlwind of energy and style and futures imagined. In Florence, she was diving deep into various art-related business opportunities, as only the descendant of a certain famous Renaissance-era family can.

Rosa had recently sent Hannah a characteristic series of text messages, which she read to me off her phone. She wanted Hannah and her husband to come help with “reviving Bucchero,” a style of pottery from the pre-Roman Etruscans. She wanted them to come to Florence. She had a place for them to stay.

And it escalated from there:

—I could really use your help at the gallery and to have someone living in the apartment. And a brilliant art historian.

—I could offer you the apartment to live in for free.

—I need your brilliance and your integrity

They could go into business together. A 50/50 split. Rosa offered my sister’s husband, Jake, a sales role and a commission split.

She put numbers to the offer, and dates:

—Please consider three months in Tuscany? I want to be friends forever! Please I miss you so much.

Right then, I loved Rosa for all her quirky devotion to my sister, and for extending so generous an offer for them to come live in Florence, to start a business, to raise the kids, to have a place, a foothold.

We should all be so lucky to have a friend like this.

Hannah and I had been debating the wisdom of leaving the near-paradise that is New Zealand and moving her family to Europe, or the UK. Somewhere closer to all of us. But how—and where?

Perhaps Northern France, where cheap and expansive country homes can be had for less than €200k? Or the UK, where my sister and her husband first met? They felt at home there, and proximity to London seemed to offer other business opportunities. But would they ever be able to afford to buy anything in the UK? It all felt so cost-prohibitive.

My current obsession was Italy (see previously: House Hunting in Italy). I’d just spent the afternoon browsing the back catalog on “Cheap Italian Dream Homes,” after all. Last year, I’d spent a week exploring the area around Lago di Garda, pausing whenever I saw a Vende sign to gaze and imagine another life.

And here was Rosa, inviting them to come visit Italy, maybe even put down roots.

My friend in New Hampshire

The winter of 2019, when I bought the house in New Hampshire, an old friend came over—it was late March, and the walkways in front of the house were still frozen over.

From the window, I saw her pull up, take a look at the walks, and then retrieve a bag of ice melt from her car. She sprinkled salt up and down the path leading to my front door, and then up the steps to the porch.

This was Jenny—one of my oldest friends in the world.

I’d bought the house for the climbing, and for the nostalgic attachment I had for the White Mountains and for New Hampshire.

What I didn’t know when I went under contract on the house, is that Jenny, my long-lost friend from middle school, who was actually not lost at all, was currently living just down the street.

About two weeks before I was set to drive up for the inspection, I saw on Facebook that Jenny was marked as being in the next town over. At that moment, I hadn’t spoken to her in almost a decade. But I was excited to maybe have a friend nearby, so I chatted her right then:

—Hi Jenny. I know it's been a loooong time, but ...

I asked if she lived in the area, and let her know I was about to buy a house in Rumney.

A few hours later, she wrote back:

—Stop. I live in Rumney.

It was almost too big of a coincidence.

I knew Jenny from 7th grade. We were “boyfriend and girlfriend” for a hot middle school second before she sent me a classic break-up poem—something about roses being red and her not wanting to be with me anymore.

We stayed friends after my family moved away to upstate New York. We stayed friends in College, and after. She moved to Santa Fe, where I was going to grad school, and there we tried to stay friends, though our paths diverged. And now, she lived a long throw from the house I was buying.

I came to Rumney for the inspection, in the dead of winter, then met Jenny for dinner, where we caught up on the last decade of our lives. Sometimes the friendships of our youth turn out to be empty in adulthood, or, as we were approaching it, middle age. Other times, like with Jenny, it turns out that friendships can endure quite a bit, even become stronger.

It’s those friendships which can make all the difference when you are in a new place, or feeling lost, or searching for home. In the months after I bought the house, I would run into Jenny at the Rumney tavern in the evenings, say hi, hug, and feel just a little less like a stranger who had just parachuted into a small rural town.

Last week, Jenny texted me that she was on her way to a swimming hole near my house with her kids, if I wanted to join. I grabbed two beers out of my fridge and drove down the road to meet her. We sat on a rock in the shade on a hot, humid day, and watched her kids play in the Baker river in the bend by the climbing area, and drank the beers.

We talked about parenthood and life and I canceled plans I’d had so I could stay a while longer.

Searching for home

New Hampshire is about to enter its utterly glorious phase: late August through October, when the leaves turn, the temperature drops, and the climbing gets even more amazing. I’m looking forward to being there for most of October—

Yet, the past year, my constant daydream has been of an Italian villa, down a long drive, surrounded by olive groves, perhaps a vineyard nearby, and an outdoor pizza oven and veranda where I can make pizza and host friends.

In this sense, Cheap Italian Dream Homes has me covered on everything—

Everything except, of course, the friends.

So let’s be realistic: buying that Italian villa would be kind of lonely. What, am I supposed to make friends with the old Italian farmer down the road? Where’s the community? Who is going to share those pizzas and that wine with me?

I often think of certain YouTubers I love to watch, who make their homes in simple, off-grid cabins (see Brooke and Dave Whipple), or beautiful yurts (see Jake and Nicolle), usually nestled into some corner of the Alaskan wilderness. Those are both couples, and one can get a lot of inspiration from their ability to live simply, but even as a couple I wonder: where is the community, where is the group of friends who can laugh together, and learn from each other? I know that every once in a while these off-grid couples will have a video with a friend, either who they visit, or who is visiting from afar.

But is that what I want from my Italian villa—to sometimes have a friend visit from afar?

This is why, when looking for places around the world to travel, I start with climbing or kitesurfing destinations. The communities are, to some extent, built into the equation. The trick will be to find the center of the Venn diagram, where the villa near the friends (or even a friend) overlaps with the nearby cliffs or the kite beach.

And the funny thing is, I already know of places kind of like this—one is New Hampshire, and I’m already living it. The other, though, if old-world Europe is what I’m after, is in Spain, not Italy. I’m going there in November to climb, and to take a look at a property or two. And I already have a friend who is going to live there; I’ve written about him before.

I just have to keep reminding myself in my olive grove-infused daydreams that actually Spain is the number one producer of olive oil in the world, and it’s not even close. Italy is a second, but a distant second indeed.

Post-Nomad

Go toward friendships