5 picture-perfect Tuscan Towns

Helen Alexander

Senior Contributor

We all know the big-hitters like Florence and Sienna, but what about smaller towns and villages that are filled with historic buildings, have stunning views of the surrounding countryside and offer a glimpse of a more local way of life? Here are five destinations you won’t want to miss during your Italian explorations.

Circumnavigate Lucca’s old city walls

Walk or cycle along 2.5 miles of scenic pathways as you circle the old town of Lucca from the top of its mura – or boundary wall. Through its long history, there have been four sets of walls built to protect the city and the 12-metre-high stone ramparts that you see today were built somewhere between the mid-1600s and early 1800s. The tree-lined route is a great way to see some of the city’s main sites, as are Torre Guinigi (a 45-metre-high Romanesque-Gothic structure that’s topped with a leafy roof garden) and the taller Torre Delle Ore (a 13th-Century clock tower than chimes – very loudly – every 15 minutes).

Gain access to the wall at the Baluardo San Regolo next to Lucca’s pretty botanical gardens, and find out why it’s a favourite location for the locals' beloved passeggiata (evening stroll). To ensure you don’t get peckish, pack some Buccellato from Buccellato Taddeucci café (Piazza San Michele, 34). Lucca’s famous bread has been satisfying sweet-toothed travellers since medieval times and is stuffed with raisins and flavoured with anise.

Rooftops of Lucca

Credit: Nic Crilly-Hargrave

Gaze up at San Gimignano’s tower-filled skyline

See what happens when wealthy families try to assert their authority and find out why San Gimignano has the nickname the ‘Manhattan of the Middle Ages’. In a bid to build the tallest tower, the charming city was once home to 72 sky-high structures. Only 13 are still standing in their entirety today, but it is possible to see the remains of some of the others within the historic centre that is now a designated UNESCO World Heritage site.

Along with the twin towers known as Torri dei Salvucci, the 54-metre Torre Grossa that’s attached to the city hall is the only tower that’s open to the public to climb. If you haven’t got a head for heights, a glass of the local white wine – Vernaccia di San Gimignano – should help ease any nerves. 

The medieval town of San Gimignano

Credit: canadastock

Explore the Monte Argentario peninsula

Connected to the mainland by two narrow causeways, the mountain-island of Argentario is surrounded by crystal-clear waters of the Tyrrhenian Sea, almost entirely covered by a beautiful national park and home to the pretty port of Santo Stefano. With its yachts, waterfront promenade designed by Giorgetto Giugiaro and smart hotels – like the cliff-top Hotel Il Pellicano – who needs the Riviera to feel like a celebrity? From here, it’s just a 50-minute boat ride to your own private (ok, quiet) island of Giglio.

On your way over to Monte Argentario, stop off at the sleepy, lagoon-side town of Orbetello, where Restaurant I Pescatori (Via Giacomo Leopardi, 9) serves up delicious, locally caught fish dishes. The eel and spaghetti alla chitarra with shavings of bottarga (dried fish roe) should not be missed and, as you tuck into your lunch, you might just spot pink flamingos and white herons wading in the water.

Monte Argentario

Credit: Nic Crilly-Hargrave

Uncover Italy’s winemaking heritage in Radda

Sitting in the heart of the country’s famous Chianti region, this is the place to familiarise yourself with a few bottles of the full-bodied red wine that takes its name from the rolling hills where it was born. At first glance, this small village might not look much more than a tangle of alleyways, but look again and you will see that at every turn there are views of vineyards and historic castles, convents and churches.

It’s the perfect location from which to access Tuscany’s chianti classic wine route – be sure to make time for a wine tasting at the nearby Montemaggio Estate and a tour of Castello di Radda’s cellars before eating dinner at its smart on-site restaurant. 

Radda in Chianti vineyard during an Autumn sunset

Credit: StevanZZ

Get lost in the hilltop town of Pitigliano

Also in Tuscany’s Maremma region, Pitigliano is an essential stop off on your way to the thermal mineral waters of Bagni San Filippo. In fact, it’s just one of several clifftop villages that make up an enchanting area referred to by locals as the ‘cities of Tufo’, named after the volcanic rock out of which they are carved – nearby Sorano and Sovana are also worth visiting. Built in the 1600s, the Medici aqueduct still dominates the city centre, while history buffs can feast their eyes on Neolithic and Bronze Age remains in the outdoor archaeological museum. If you are staying the night, it’s worth heading down to the valley below at dusk to see Pitigliano lit up each evening.

Another city worth the steep climb is nestled between Tuscany and Umbria in the lesser-known province of Lazio. Accessible by a narrow suspension bridge that’s only open to people crossing on foot, entering Civita di Bagnoregio is like stepping back in time. Filled with Renaissance buildings and rustic trattorias, it is the perfect place to soak up a slower pace of life.

Stunning view of Pitigliano

Credit: Nic Crilly-Hargrave

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