Day 1: Lucca

Our road trip starts in Lucca, a pretty town nearby Pisa’s Leaning Tower.

Hometown of opera composer Giacomo Puccini, Lucca is a truly fascinating place with a wealth of impressive architecture, fine art and cheerful cafes.

Day 2: Volterra, San Gimignano

About 1.5 hour drive from Lucca, Volterra is a pretty hill town founded by the Etruscans more than three thousand years ago.

From Piazza dei Priori, one of Italy’s most beautiful medieval squares, it’s a delightful maze of narrow streets and alleys lined with ancient buildings and small craft shops selling alabaster, the stone Volterra is famous for.

Day 3: Monteriggioni, Chianti, Siena

Our first stop on the way to Chianti was Monteriggioni, a hilltop village surrounded by thick stone walls.This place is tiny, with lots of cute craft shops and cafes.

Day 4: Siena

A must-see on any trip to Tuscany, Siena is a charming, elegant town filled with superb examples of medieval architecture and rich artistic treasures.

One of the most fascinating aspects of Siena is that it is divided into 17 neighborhoods called contrade, each with its own constitution, traditions and history – and locals have a really strong sense of belonging to their own contrada!

Day 5: Crete Senesi, Montalcino, San Quirico d’Orcia

Time to venture through what I reckon to be the prettiest drive in Tuscany, Crete Senesi, so called because of the distinctive clayish colouration of the soil which gives the landscape a lunar appearance.

Days 6-7: Val D’Orcia

Val d’Orcia is a land rich in history and scenic corners, home to some of the prettiest villages in Tuscany, with rolling hills in all shades of green and yellow punctuated by rows of vineyards, cypresses and stone farmhouses.

Day 8: Montepulciano, Cortona

It took me about 30 minutes to reach Montepulciano from San Quirico.

This is another beautiful Tuscan medieval gem, famous for its elegant palaces, ancient churches and excellent wine.

Day 9: Valtiberina

From Cortona we drive through winding roads into to the heart of Valtiberina, a beautiful  corner of Tuscany at the border with Umbria that is still unknown to tourists.

Day 10: Arezzo and back home

About 40 minutes from Sansepolcro, Arezzo is the capital city of eastern Tuscany.

Although it gets far less attention than Florence and Siena, this beautiful town has plenty to offer, with a rich art and architecture.