Sometimes the Best Days Aren’t Planned

One of the things I love most about Tuscany is that some of the best days aren’t built around a long list of things to see.

We started this particular day with coffee in Panzano before making our way to Greve in Chianti. It was early November, the crowds had thinned, and when we arrived at Piazza Matteotti, there really wasn’t much of an agenda.

We found a spot for lunch, wandered around the piazza and simply enjoyed the slower pace of the town. No rushing to the next reservation. No checklist of sights we needed to get through.

And while strolling through Greve, we wandered into what may be one of the best butcher shops I’ve ever visited. It’s one of those places you could easily spend far more time in than you expected.

That’s the Tuscany I tend to remember.

An Added Bonus: Montefioralle

Just up the hill from Greve is Montefioralle, a tiny medieval village surrounded by the vineyards of Chianti.

It’s the kind of place you might not have heard of before arriving in the area — and that’s part of what makes it so good.

Park outside the village and start walking. Wander the stone lanes, take in the views across the vineyards and don’t worry about finding the next attraction. There really isn’t one you need to rush toward.

Sometimes the places you weren’t planning to see are the ones you remember most.

A Few Things I’ve Learned Traveling Italy

Days like this have changed the way I think about traveling — and planning trips — in Italy.

You don’t need every day filled with tours and reservations. Leave some room to stop for coffee in a town you weren’t planning to visit. Have a long lunch. Wander into a shop because it looks interesting. Take the road up the hill just to see what’s there.

And especially in Tuscany, having a car for part of your trip can open up an entirely different side of Italy. The smaller villages, wineries and countryside stays are often the experiences people remember long after they get home.

Most importantly, slow down.

Don’t try to see everything when you haven’t seen anything yet.

Thinking About Italy?

If Italy is on your list for 2027, this is exactly the kind of trip I love helping people put together — combining the places you’ve dreamed about seeing with smaller towns, countryside stays and experiences you may never have known to look for.

I’ve put together a collection of Curated Italy Journeys to give you ideas for what your own trip could look like, from slower stays in Tuscany to Rome, Florence, Venice and the Amalfi Coast.

EXPLORE ITALY JOURNEYS →

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Buon Viaggio, 🇮🇹

Dan
Nomad With Dan

Experience Italy. Don’t just see it.

P.S. Have a question about Italy? Just reply to this email—it comes directly to me. I’m always happy to talk Italy. 🇮🇹