A medieval stronghold of wine and lively Italian spirit

Tranquillity awaits Phil Thomas around every Certaldo street corner, where great food and drink flow with a unique history

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There's something not quite right, I realise, as my eyes scan the gelateria counter in Certaldo, a small Tuscan hilltop town.

“Vanilla, strawberry, pistachio... onion?!”

The server, who’s clearly seen this bemused reaction before, grins.

“Si,” she exclaims proudly. “È delizioso. Solo qui!”

Perhaps it’s “only here” for a reason – the gelato certainly leaves an unforgettable first impression. The sweet, sharp taste drawn from Certaldo’s signature ingredient elicits the Italian equivalent of a Marmite reaction. People either love or hate it.

Certaldo doesn’t grace the cover of Tuscan guidebooks. In truth, it’s often overlooked altogether. But the walkable medieval streets, standout food, and views that go on forever make it my ideal Tuscan base.

The town also offers an antidote to Tuscany’s notorious summer traffic: a frequent train from Pisa, with one easy change, gets us there in under an hour – with direct routes from Siena and Florence, too. From the station, it’s just a two-minute walk and a short funicular ride to the old town, Certaldo Alto. We climb 200 metres and are deposited into the 14th century.

During my years coming to Certaldo, I’ve asked many locals what sets it apart from its more famous neighbours. The most common answer is that “people still live here”. Certaldo may look like a period drama set, but behind its shuttered windows, life quietly carries on.

The narrow lanes and crenellated skyline speak to Certaldo Alto’s heyday as a medieval hilltop stronghold. There’s no central piazza, just a weave of medieval streets winding up to the 12th-century Palazzo Pretorio. Once home to the ruling podestà, or chief magistrate, it’s now a time capsule, complete with carved coats of arms and 600-year-old prisoner graffiti.

It may look frozen in history, but every so often, Certaldo reminds you it’s very much alive.