With stunning scenery, incredible art and architecture, and some of Italy’s best wine, Tuscany draws travelers back year after year. The rolling hillsides, ancient vineyards, and olive groves create a beautiful backdrop for the well-preserved medieval cities where you can truly enjoy the good life, Italian style.

The two largest cities in Tuscany, Florence and Pisa, attract tourists by the score. But it’s Tuscany’s smaller villages and towns that most captivate visitors. If you have the time, plan to visit several. Despite their proximity, each is unique – and special – in its own way. Use our map of Tuscany to plan your trip.

1) Lucca
No visit to Lucca is complete without a stroll or bike ride through the park that rests atop the 15th-century walls encircling the city. Walk along Lucca’s narrow streets, and you’ll run into a church almost immediately – there are 99 of them in Lucca. The gorgeous, crescent-shaped Piazza dell’Anfiteatro traces the lines of the old Roman amphitheater.

2) Volterra
Surrounded by quarries where the local alabaster was mined, Volterra sits perched on a rocky promontory. Its 3,000 year history is easy to explore with Etruscan, Roman, and Medieval sites and museums.

3) San Gimignano
With its medieval skyscrapers, San Gimignano has one of the most distinctive skylines in the region. Fourteen of the original 70 towers remain, but San Gimignano also boasts beautiful churches, museums, and convents from the Middle Ages.

4) Monteriggione
The only town in the region with intact walls, Monteriggione has a 14th-century parish church, a Romanesque abbey, and beautiful ceramics and leather goods.

5) Siena
Siena’s Campo is arguably the most beautiful public square in Tuscany. Little changed since the 14th-century, Siena seems almost lost in time. Thankfully, most of the city is closed to cars. Exceptional early Renaissance art and a vibrant local culture – best seen in the no-holds-barred Palio horse race run here twice a year – make Siena a must-visit destination.

6) Montalcino
Wine lovers must make a pilgrimage here to sample Brunello di Montalcino, one of Tuscany’s best red wines. Wine cellars are available in town for tastings or you can arrange to visit one of the wineries nearby.

7) Pienza
From the outside, Pienza looks like another Tuscan hill town. But thanks to its association with Pope Pio II, Pienza has a superb Renaissance complex designed by Alberti. While you’re here, be sure to sample the world-renowned Pecorino cheese.

8) Montepulciano
A top destination for oenophiles, who come to taste the Vino Nobile wines made here, Montepulciano also has a beautiful Renaissance church just outside the town walls. The location, nearly 2,000 feet above sea level, provides sweeping views of the surrounding countryside.

9) Cortona
Best known from Frances Mayle’s book, Under the Tuscan Sun, Cortona is surrounded by vineyards and olive groves. In the town – which escaped damage in World War II – you can see exquisite paintings by Fra Angelico and Luca Signorelli. And there are beautiful views of Lake Trasimeno

10) Arezzo
For a town its size, Arezzo has a lot to see, including a Roman Amphitheater, the House of the poet Petrarch, an archaeology museum, and several fine churches. There’s a huge antiques fair here the first weekend of the month.

Find more places to visit in Italy.

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