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Our Favourite Towns & Villages

We created these pages to help you really Discover Italy. Journalists Donald Strachan and Steve Keenan — who visit several times every year — have gathered a rich crop of local stories and written destination guides to help you make the most of your vacation. As they say in Italy, “Buon viaggio!”

Colle Val d’Elsa

Perched on a cliff beside the road to San Gimignano, Colle Val d'Elsa is famed for its craftsmanship. Here you can walk medieval alleys, buy from one of Tuscany’s finest modern ceramics workshops, and tour the birthplace of the legendary architect Arnolfo di Cambio, builder of Florence's Palazzo Vecchio.

Barberino Val d’Elsa

Pretty, fortified and peaceful, the village of Barberino is midway between Florence and Siena, on an outcrop above the Elsa and Pesa valleys. Its architecture and layout are typical of the Tuscan Middle Ages, with stone gates guarding entrances north and south. The surrounding countryside has Etruscan burial grounds and some of Tuscany’s best rustic food.

Elba

Around 10 miles off the mainland, the island of Elba has some of Tuscany’s best beaches surrounding a rocky interior covered in Mediterranean macchia vegetation. Here you'll find Napoleon’s residences from a brief time spent in exile, plus a summit cable-car ride and beautiful white sands.

Empoli

Understated and under-visited, Empoli provides a proper glimpse into the rhythm of life in small-town Tuscany. The centre has its own forgotten frescoes, and nearby are the birthplace of Renaissance genius Leonardo Da Vinci and a Medici villa notorious for a high-society murder in 1576.

Montalcino

Mighty fortifications high above the old road from Siena to Rome announce your arrival at one of Tuscany’s loftiest hill-towns. Montalcino is known around the world for its iconic red wine, Brunello di Montalcino. Less famous are its 12th-century abbey and an intact castle where the Sienese Republic’s last stand played out.

Pitigliano & Around

Pitigliano seems to grow from a single crag. Even if you look closely, it’s hard to tell where houses end and the bedrock begins. Its labyrinth of narrow streets, stone staircases and vaulted passages is unlike anywhere else in Tuscany. Come here for centuries of Jewish history and a landscape criss-crossed by mysterious Etruscan pathways.

Radda in Chianti

Radda is the classic Chianti town. This sunny cluster of buildings and lanes is surrounded by a rolling ocean of grape vines. You’ll find medieval fortifications, photogenic Chianti scenery, and lots and lots of wine. A 15-minute drive north-east to the hamlet of Volpaia is one of the prettiest in Tuscany.

Greve in Chianti

Greve is surrounded by classic Chianti country — just like you’ve seen in photos, Renaissance paintings and your dreams. The best-known stop on the Chianti Road is home to fine wine by the barrel-load, memories of two historic North American explorers, and some of Tuscany’s most famous butchers.

Castellina in Chianti

A hilltop town on Tuscany’s Chianti Wine Road, Castellina was an original member of the medieval Chianti League defensive alliance. It retains the look of a fortified outpost. Its mighty castle is intact, but these days surrounding hills are where you’ll discover fine Tuscan food and highly regarded red wine estates.

Todi

Todi is a tranquil town with fine views from high on its hill above the River Tiber, across hills dotted with isolated hamlets, olive groves, sunflower fields and rolling farmland. Here you'll find peaceful isolation; ancient Roman tunnels below its narrow, medieval streets; and Piazza del Popolo, Umbria’s prettiest square

Gaiole in Chianti

Gaiole is the main market town of south-eastern Chianti, in the hills north-east of Siena. Grapes for some of Italy’s most prestigious reds grow in almost every direction. Nearby outside the centre are the "Road of Castles”, contemporary art installations, and the spiritual home of modern Chianti winemaking.

San Gemini

In the heart of Umbria, San Gemini is a quiet, unassuming place where seasons ebb and flow — and the Umbrian delicacies on dinner plates with them. Locals enjoy the good things in life, largely untroubled by tourism. A short journey from its tranquil streets, you'll find Europe’s tallest man-made waterfall and the ruins of a Roman resort.

Portofino

Portofino is the jewel of Liguria’s Riviera di Levante, a simple fishing port whose impossible beauty made its name and where La Dolce Vita never ended. Beyond its multi-coloured Mediterranean harbour are medieval churches and a 10th-century abbey you can only reach on foot or by ferry.

San Gimignano

One of Italy’s most spectacular hill-towns, San Gimignano is famed for its 13 surviving medieval towers, the frescoed 15th-century interior of its Collegiate Church, and a fine white wine made from grapes picked on the surrounding hills, Vernaccia di San Gimignano.

Montepulciano

Southern Tuscany’s highest hill-town snakes along a ridge overlooking vineyards and the fertile Valdichiana. With its perch above a sea of Sangiovese vines, nature has been the town’s best friend. Here you'll find palace architecture by Sangallo, artisan workshops, and one of Italy’s great red wines.

Cortona

Cortona shot to fame as the star of Frances Mayes’ “Under the Tuscan Sun”, a travelogue bestseller turned Hollywood film. The town has an intact Medici fortress, a deserved rep for its handmade ceramics, and museums stuffed with everything from Etruscan treasure to Renaissance paintings.

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