12-day tour of Tuscany | Lucca, Chianti, Siena & Florence

Day 1: Departure to Florence for the start of your tour of Tuscany After landing, pick up your hire car and drive 100 kilometres to the Lucca area, where you will stay in a historic villa. If you wish, you can visit Prato on the way, with its cathedral and beautiful frescoes by Filippo, or Pistoia, with its medieval Piazza del Duomo.

Day 2: Pisa and Lucca

The Leaning Tower of Pisa, in the harmonious Piazza dei Miracoli, is one of the most visited monuments in the world. The tower, with its refined architecture, is the campanile of the nearby Duomo, with its marble façade and bronze doors. Inside, you can admire the imposing 14th-century pulpit by Pisani. The beautiful octagonal baptistery completes the picture. Continue on to the walled town of Lucca, a very pleasant town with charming squares and the picturesque Via Fillungo, full of lovely shops. Be sure to take the time to sit on a terrace in the beautiful Piazza dell'Anfiteatro, built on the remains of a Roman theatre. The imposing city walls with their shady tree-lined avenues are wonderful for walking, cycling or picnicking, with a beautiful view of the city and the surrounding area.

Day 3: Carrara and Pietrasanta

Near Carrara, you can visit the spectacular white marble quarries, where Michelangelo probably sourced the marble for his “David”. On the way back, be sure to stop in Pietrasanta, a cosy artists' town with charming shopping streets.

Day 4: to the Chianti region with rolling hills

You are expected in this famous wine region, where you will stay in the renowned and centrally located Chianti region. Here you can enjoy delicious wines from the Chianti region. If you wish, you can stop off in Monteriggioni, a walled town with a spectacular location and a circular defensive wall with 14 towers.

Day 5: Medieval city of Siena

Cor magis tibi Sena pandit', Siena opens its heart to you. So it is written on one of the gateways to this delightful medieval city of Siena. Charming streets lead to the stunning Piazza del Campo with its Fountain of Joy and Gothic Palazzo Pubblico, accompanied by the 102-metre-high Torre della Mangia. There is also the Duomo with sculptures by Michelangelo and Pisano and a beautiful inlaid marble floor.

Day 6: San Gimignano and Volterra

The tourist town of San Gimignano is best known for its tall, slender towers, which can be seen from far outside the town. Originally there were 72, but today only 13 remain standing. No wonder the town is also known as the “New York of the Middle Ages”. The medieval “Piazza della Cisterna” is named after the 13th-century well in the square. Then you continue to the walled town of Volterra, with its Etruscan museum.

Day 7: The Chianti villages

Along winding roads and beautiful landscapes, you will explore the small villages of Castellina, Greve, Radda and Gaiole in Chianti. North of Castellina lies the Badia a Passignano, a magnificent abbey founded in 1049. Near Greve, in Montefioralle, Amerigo Vespucci was born, and near Gaiole lies the imposing Castello di Brolio. This is where Bettino Ricasoli, a well-known 19th-century politician and oenologist, died. He paved the way for Chianti wine to reach the rest of the world, known for its delicious wines.

Day 8: the Crete Senesi and Montepulciano

A long but beautiful trip takes you to the enchanting landscapes southeast of Siena today! You will drive through the “Crete Senesi”, with its rolling cornfields, sometimes dotted with poppies. Via the village of Asciano and the Abbazia di Monte Oliveto Maggiore, with its masterful frescoes, you will head to the “ideal town” of Pienza. You will end the day in the Renaissance town of Montepulciano for a glass of the delicious Vino Nobile wines.

Day 9: to the Arezzo area

Today you will depart for Arezzo, where you will spend three nights in a small hotel 8 kilometres from the city.

Day 10: Florence

Florence is a beautiful city and the cradle of the Renaissance. Discover the imposing dome of Santa Maria del Fiore, the medieval bridge “Ponte Vecchio” and numerous museums, including Gli Uffizi and the Palazzo della Podestà. Explore the lively centre on foot, passing elegant boutiques and beautiful squares with terraces. Caractère can also arrange a Dutch-speaking guide for you.

Day 11: Arezzo and Cortona with beautiful frescoes

Arezzo boasts a charming Piazza Grande and the Santa Maria della Pieve church with its beautiful bell tower. In the Basilica of San Francesco, you can admire the beautiful frescoes by the painter Piero della Francesca. Continue on to the lovely medieval town of Cortona, with its unforgettable views of the surrounding area.

Day 12: Return home

Your trip is over and you drive back to Florence Airport, where you take the plane back home.

Frequently asked questions about enjoying Tuscany in style

Do I need a hire car for this tour of Tuscany?

Yes. You will be driving between Lucca, the Chianti region, Montepulciano, Arezzo and the Crete Senesi. Many villas and villages are not accessible by public transport. You can take the train to Florence if you wish.

When is the best time for a tour of Tuscany?

May, June and September are ideal: pleasant temperatures and less crowds in Florence, Siena and San Gimignano. July and August are warmer and busier.

What makes this tour different from a short city trip to Florence?

You see more than just Florence. You stay among vineyards, drive through the Crete Senesi, visit Siena, Montepulciano, Arezzo and small villages that you would miss on a city trip. Less museum marathon, more Tuscany.