Forget Florence: six of the best towns in Tuscany to escape overtourism | Tuscany holidays

Although steps are being taken – the city council has introduced a ban on new short-term lets and is promoting sights in lesser-known neighbourhoods – tackling overtourism is a challenge. And other Tuscan cities, such as Siena and San Gimignano, are suffering too. But beyond these honeypots, Italy’s fifth-largest region is full of glories, with not a takeaway chain or selfie stick in sight. Here are six of my favourites.

For architecture: Monteriggioni

To hit Monteriggioni during its medieval festival in July is to be transported to the middle ages: the whole town becomes a stage on which local re-enactors recreate 13th-century life, with artisans, entertainers, soldiers and musicians in the streets, and inns serving ancient recipes. Festival apart, this tiny town is remarkable for its intact architecture. It was built by the Republic of Siena around 1213 to ward off Florentine aggression, and it is still possible to walk around its 570 metres of wall, with two gates and 14 watchtowers. Inside there is a church, a museum and gardens once used to grow food in case of a siege. All cobbled streets and panoramic views, it feels intimate but rarely crowded. On the square, Il Tagliere Medievale is the place to people-watch over cured meats and cheese and a carafe of chianti.
Stay at Il Piccolo Castello, doubles from €115 B&B

For idealists: Pienza

Is there such a thing as an “ideal city”? In 1459, Pope Pius II rebuilt his birthplace, Corsignano, according to the scientific and humanist criteria architects and planners believed cities should fulfil, with harmoniously proportioned streets, buildings and fortifications. Naturally, he then renamed the town after himself. Pienza is tiny – about 2,000 inhabitants – and best explored on foot. The main square, Piazza Pio II, is a small space shared by the cathedral and the honey-coloured Piccolomini Palace, Pius’s summer residence. The three colonnaded loggias (covered walkways) facing the Piccolomini’s garden suggest the harmony architect Bernardo Rossellino was aiming for. Human harmony is evoked by street names Via dell’Amore and Via del Bacio (kiss): both lead to a walkway with panoramic views over the Val d’Orcia. Foodwise, Pienza is known for its pecorino cheese: try it at La Terrazza del Chiostro, run by young chef Massimiliano Ingino.
Stay at Agriturismo Casalpiano, doubles from €135 B&B

For Renaissance art: Arezzo

On a hill where eastern Tuscany rises to the Apennines, Arezzo is rich in history and art, but sees a fraction of Florence’s visitors. Many come for the monthly antiques fair on Piazza Grande, the sloping main square. The city’s treasure is the 15th-century artist Piero della Francesca’s Legend of the True Cross frescoes in San Francesco basilica, but I also love his serene Mary Magdalene in the cathedral up the road. From there, it’s a short walk across Passaggio del Prato park to the fortress built by the Medici family in 1540. Its ramparts offer great views over red roofs and rolling countryside. In pedestrianised Via Cavour, three friends recently took over a former corset shop and turned it into a deli selling filled focaccia, wine, chocolates and olive oil.
Stay at La Corte del Re, doubles from €79 room-only

For history: Volterra

Volterra was founded about 3,000 years ago as part of the Etruscan league of 12 cities. Its Guarnacci museum features hundreds of fantastically decorated funerary urns, but they’re outshone for me by an elongated male nude in bronze called Shadow of the Evening which, though believed to have been made in the third century BC, wouldn’t look out of place in a modern sculpture show and is said to have inspired Giacometti. A short walk away, the Porta all’Arco is an Etruscan gate still standing after 2,300 years. More recent monuments include a Roman amphitheatre and a Medici fortress now used as a prison. The town is also known for alabaster carving: check it out at the Ecomuseum, or buy at local cooperative Artieri Alabastro. In a picturesque alley, La Sosta del Priore (Prior’s Pitstop) offers sandwiches with fillings such as wild boar, melted pecorino and lampredotto (tripe).
Stay at Villa Nencini, doubles from €65 B&B

For port city vibes: Livorno

Tuscany has so many sights that its ancient port is often overlooked. Originally fortified by the Pisans, Livorno was ruled by Florence’s Medicis from the 1500s, and today’s multicultural vibe is thanks in part to that dynasty. Under Medici law, newcomers of any nationality or faith were encouraged to settle here, and a diverse population – Greeks, Armenians, Jews fleeing the Inquisition – helped Livorno thrive. Today, this politically leftish and greenish city is home to populations from Senegal and Morocco as well as eastern Europe.

Get a lungful of sea air at the checkerboard seaside promenade Terrazza Mascagni, then walk up to the Quartiere Venezia, Livorno’s Little Venice, with bridges, coloured houses and two Medici fortresses, Nuova and Vecchia. Other sights include San Francesco Cathedral and one of Italy’s biggest covered markets, the Parisian-style Vettovaglie. Livorno is known for its chickpea pancakes (torte di ceci), and Torteria Gagarin by the market sells them hot from a wood-fired oven to eat in a roll as a cinque e cinque sandwich.
Stay at Dogana d’Acqua Rooms & Art, doubles from €75 room-only

For coastal charm: Porto Ercole

A port since Roman times, this village on a promontory in the south of Tuscany was fought over in 1555 in a proxy war between Spain (supporting Florence) and France (Siena). Spain won and built the forts that still guard all approaches. Climb up to Forte Stella for views over the picturesque harbour and north to one of three causeways linking the promontory to the mainland. The walk into town passes the botanical garden. Farther north is the unassuming cemetery that is home to Caravaggio’s simple tomb, an odd finale to a life of brawls, murders, arrests and exile. Mystery surrounds the painter’s death, but he was said to be heading for Rome in the hope of papal forgiveness when he succumbed to “fever” – probably infection from a sword fight in Naples.

For a beach day, head out on the SP66 and take the signposted footpath just before the crossroads leading to Forte Stella. Sandy Spiaggia Lunga is mostly undeveloped, but in high summer there’s a bar with sunbeds to hire. Right on the harbour back in Porto Ercole, Grano offers top-quality sourdough pizzas by the slice.
Stay at Alba sul Mare, doubles from €91 room-only