Top Towns in Tuscany

A great way to discover Tuscany is to get out of Florence and into one 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. Therefore, if you want to get a break from the city, a local experience, or the feeling that you have entered an Italy of the past, we suggest that you head to some of the towns on this list. In addition, they all make for a great side trip if you are joining us any time soon at Villa Ferraia for our new Tuscan Cooking School adventure!

Lucca

About an hour northwest of Florence, Lucca is one of those towns where you can escape the crowds of Tuscany’s main cities while enjoying all of Italy’s urban beauty. On the outside Lucca is surrounded by Renaissance walls that are topped by tree-lined avenues perfect for biking or walking, and on the inside it is 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 is 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 hill town 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 will see they seem to end in air, giving a sense of an island in the sky. A trip to Montalcino would not be complete without a drive through the countryside to discover some of the even smaller town’s one more sleepy than the next where every glass of wine is a treat.

Volterra

The small hill town of Volterra recently gained fame from Stephanie Meyer’s Twilight novels. However, this influx of tourists has not 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. However, 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 are 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 hill town, 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 cannot spoil the natural beauty of the island. Far up on the hill, Castello is one of the three towns on the island. Its 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.