In Search of a Quiet Tuscan Haven? This Is It.

A medieval village with $550 rentals, panoramic views, and easy access to all of Tuscany.

After five and a half years of slow traveling across the globe, with two dogs in tow and passports heavy with stamps, Warren and I thought we’d seen it all. But then we arrived in Certaldo Alto.

Nestled in the Tuscan hills halfway between Florence and Siena, Certaldo Alto doesn’t shout to be noticed. It whispers. And we heard it loud and clear.

We arrived in February, having just left the frozen peaks of Brașov, Romania. As we crossed the Italian border, the snow disappeared and Tuscany opened its arms. Sunshine. Olive groves. Wine country. And best of all, Certaldo, our new base for two and a half months.

Certaldo is a town of two halves. Certaldo Basso, the lower modern section, is where life hums along with supermarkets, bakeries, and local families. Then there’s Certaldo Alto, the medieval crown jewel perched on a hilltop above. That’s where we stayed.

There’s a funicular railway (€2 round trip) that whisks you from Basso to Alto in minutes. At the top? Red brick buildings from the 12th century, cobbled lanes, cafes with outdoor wine tables, and sweeping views over Tuscany’s postcard-perfect countryside. It’s the kind of place that forces you to slow down—in the best way possible.

We made Certaldo our home base, but its strategic location allowed us to explore widely:

• Florence and Siena are just under an hour by train.

• San Gimignano, the towered city, was visible from our apartment and just a short drive away.

• Pisa, Lucca, and the medieval walled town of Monteriggioni were all easy day trips.

• We even found a dog-friendly beach (Single Fin, Tuscany) an hour away on the coast.

But some of our favorite days were spent doing… well, not much. Strolling parklands that look like living oil paintings. Grabbing cappuccinos and focaccia pistachio sandwiches from the local Forno Moderno. People-watching in Certaldo Alto’s sunlit piazzas. Or wandering into a museum dedicated to Giovanni Boccaccio, the town’s most famous son.

The cost of living here surprised us, too. We found one-bedroom rentals for around $550/month—even in Certaldo Alto. A cappuccino and pastry? Under $6. A bottle of local wine? $2.50. Even real estate here is still shockingly affordable by Tuscan standards.

Certaldo Alto may not have the buzz of Florence or the grandeur of Siena, but it’s got something else: peace. Charm. And room to breathe.

And we captured it all for you in this new video.

— Warren and Julie Knox

Read Warren and Julie’s full report here.

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Editor’s Note: Certaldo Alto is just the beginning—uncover affordable, under-the-radar towns and villages our correspondents have highlighted for their charm, cost‑of‑living perks, and quality of life.