Originally Published: September 3, 2013

A great way to discover Tuscany is to get out of Florence and into one (or many!) of the region’s charming towns. Perched on top of dramatic hills or settled into the rolling countryside, Tuscan towns are usually as stunning from the outside as they are from within. So if you want to get a break from the city, a more local experience or the feeling that you’ve entered an Italy of the past, we suggest that you head to some of the towns on this list. And they all make for a great side trip if you’re joining us any time soon at Villa Ferraia for our new Tuscan Cooking School adventure!

Tuscany Cooking School

Lucca

About an hour northwest of Florence, Lucca is one of those towns where you can escape the crowds of Tuscany’s main cities (Florence and Pisa) while enjoying all of Italy’s urban beauty. On the outside Luca is surrounded by Renaissance walls that are topped by tree-lined avenues perfect for biking or walking, and on the inside it’s all narrow streets perfect for getting lost. Check out the two churches—San Michele in Foro and the Duomo, or Cattedrale di San Marino— at night when their lit up, elaborate facades drip with white and shadows.

Siena

Only slightly larger than Lucca, Siena is another lovely town in Tuscany. Every twisting cobbled street seems to pour into the town’s iconic main piazza, called Il Campo, which is sloped and shaped like a shell. This is where the famous horse races, or palio, happen biannually. Towering out of the piazza’s periphery is the Palazzo Publico and its tall tower—climb 503 stairs for some sweeping views of the city and the countryside. Then there’s the Duomo, a stunning striped church that seems too big, visually and physically, for not only its piazza but also the whole town. Go inside and be awed by its frescoes, the tall gothic columns and its intricate marble floor.

Montalcino

The small hilltown of Montalcino is most famous for the vineyards that cover the surrounding countryside and produce the grapes for Brunello, a full-bodied red wine. Montalcino wakes up in the evenings when locals and tourists head to enotecas to enjoy glasses or bottles of the delicious wine with local snacks or dinner. Wander the narrow streets during the day and you’ll see they seem to end in air, giving a sense of an island in the sky. A trip to Montalcino wouldn’t be complete without a drive through the countryside to discover some of the even smaller towns—one more sleepy than the next—where every glass of wine is a treat. (If you’re driving to Montalcino you might want to stop by Pienza or Montepulciano, two more Tuscan towns—there are just too many for a single list!)

Tuscan Villa

Volterra

The small hilltown of Volterra recently gained fame from Stephanie Meyer’s Twilight novels. But this influx of tourists hasn’t spoiled the town’s windy charms, perched as it is on the top of a high plateau enclosed by volcanic hills. The medieval part of Volterra was built with a local yellow-grey stone, and like many other Tuscan towns, it has its own, small, collection of Renaissance pieces. But Volterra’s history is older than the Middle Ages and the Renaissance: it began with the Etruscans. It was one of the oldest Etruscan communities, known as Velathri, so no wonder it has an important archeological museum known throughout the country.

Castello, Isola del Giglio

If you’re looking to get far away from the crowds and to a place where you might not hear any language besides Italian, then you should head to Isola del Giglio and its romantic hilltown, Castello. The island made international news a year ago when the Costa Concordia cruise ship sank near the Port. Now the big boat lulls in the Mediterranean waters, but can’t spoil the natural beauty of the island. Far up on the hill, Castello is one of the three towns on the island. It’s high location gives way to stunning views of umbrella pine forests and the amazing Mediterranean sea. Escape to the town’s narrow lanes, the hiking trails that fan out from its old centre, the beach and the irresistibly slow pace of island life that makes even the sleepiest Tuscan town seem bustling.

Do you have a favourite town in Tuscany?

For more travel information about Tuscany, read our guide to the best foods in Tuscany.

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Contact [email protected] with Blog Enquiry in the subject title for any feedback or requests for a topic you want us to cover. Voted one of the best things to do in Rome, Eating Italy Food Tours offer Rome tours through one of Rome’s oldest and most characteristic neighborhoods, as well as a 3-day cooking course in Tuscany.

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