My neighbor’s family did something I can’t stop thinking about.

One of four siblings bought a house in Volterra, a hill town in Tuscany, on someone’s recommendation. Then the other three followed.

Four American siblings. Four separate houses, all close together, in the same small Italian town. They go every year, and they plan to retire there.

I’m jealous. I’ll just say that up front.

The part you can’t research

Most of what I write about here is the practical side. Mortgages. Agents who stop answering. Inspections, fees, listings that don’t come with a kitchen. That’s the part you can research.

The part you can’t research is the people.

When I picture an apartment in Rome, I can picture the building, the neighborhood, the walk to get coffee. What’s harder to picture is the life around it. Who you see. Who notices when you’re back.

The few-weeks problem

I’m still based in LA. For the foreseeable future, any place I buy in Europe is somewhere I’d be for a few weeks at a time, then gone for months.

That’s fine for an apartment. A property manager can look after an apartment. It’s harder for a life. Friendships, routines, the café where they know your order: those usually come from being around, and being around is the one thing a part-timer can’t do.

I don’t have a good answer to this yet. It’s one of the questions I take most seriously and talk about least.

What the siblings figured out

The siblings have something I’d love to have figured out. When they go to Volterra, they already have people there. Four houses, close together. They don’t have to start from zero every time they arrive.

I’m not suggesting anyone talk their siblings into buying property in Italy. My family would be lucky to organize a reunion. But it changed how I think about the question.

The question underneath

Maybe the decision isn’t only which city. It’s also who’s there, or who might come with you, or how you’d build that a few weeks at a time.

I don’t know my answer yet. But it’s becoming as important to me as where I actually buy.

— Joe

If you’ve built a life somewhere you only spend part of the year, how did you find your people? Hit reply. I read every one.