Authentic Tuscany: 9-Day Road Trip

Today, drive to Cortona (approx. 1 hour and 30 minutes from Florence), a charming hilltop town filled with history, art, and stunning panoramic views. You’ll be spending one night here.

Suggestion For The Day:

• Upon arrival, wander through Cortona’s medieval streets, lined with artisan shops and cozy cafés. Visit Piazza della Repubblica, the lively main square, and the Cathedral of Santa Maria Assunta.
• If you’re interested in history, stop by the MAEC – Museum of the Etruscan Academy, which houses fascinating local artifacts. For breathtaking views, walk up to the Basilica di Santa Margherita and the Fortezza del Girifalco, perched high above the town.
• In the evening, enjoy a traditional Tuscan dinner at a local trattoria, paired with a glass of Vino Nobile di Montepulciano from the nearby region.

Today, drive to Chianciano Terme (approx. 1 hour and 30 minutes from Cortona), with a stop in Castiglione del Lago along the way. You’ll be spending two nights in Chianciano Terme.

Suggestion For The Day:

• On your way, stop in Castiglione del Lago, a charming town perched on the northwest shore of Lake Trasimeno. Wander through the medieval streets of the old town and admire the well-preserved Rocca del Leone, a fortress offering panoramic views of the lake and surrounding hills.
• Take a leisurely stroll along the lakeside promenade, enjoy a coffee at a local café, or explore the Palazzo della Corgna, a Renaissance palace with beautiful frescoes and gardens.
• After your visit, continue to Chianciano Terme and check into your hotel. Spend the late afternoon relaxing at one of the town’s thermal spas, such as Terme Sensoriali, where you can experience aromatic steam baths, salt pools, and wellness circuits.
• Dine at a cozy local restaurant like Ristorante Rosso Vivo or La Torretta, where you can savour handmade pasta, truffle-based dishes, and fine Tuscan wines.

Suggestion For The Day:

• Today, explore the scenic heart of Val d’Orcia - Begin your morning in Montalcino a historic hilltop town with a fortress, medieval streets, and panoramic views. Visit the Diocesan Museum of Sacred Art or a local enoteca to sample Brunello di Montalcino, one of Italy’s finest wines.
• Next, drive to San Quirico d’Orcia, a charming walled town with beautiful churches and the Horti Leonini gardens. Wander its streets, browse artisan shops, and enjoy classic Tuscan landscapes of rolling hills and cypress-lined roads.
• Finish your afternoon in Bagno Vignoni, known for its thermal water pool in the main square. Stroll the historic streets, admire the stone buildings, and relax with a coffee or gelato.
• Return to Chianciano Terme for dinner at a local trattoria, sampling pici pasta with truffle, wild boar ragu, or other Tuscan specialties.

Today, drive to Siena (approx. 1 hour and 30 minutes), stopping along the way in the small village of Chiusure. You’ll be spending one night in Siena.

Suggestion For The Day:

• Begin your morning in Chiusure, a peaceful Tuscan village surrounded by rolling hills and olive groves. Take a short walk to admire the breathtaking views of the Crete Senesi landscape and enjoy a relaxed coffee or light lunch at a local café before continuing your journey.
• Upon arrival in Siena, start your exploration at Piazza del Campo, one of Europe’s most famous medieval squares. Then visit the magnificent Duomo di Siena, and consider purchasing a joint ticket to access the crypt, baptistery, and museum for a complete experience.
• Don’t miss Torre del Mangia, Palazzo Pubblico, Santa Maria della Scala, and the Basilica Cateriniana, which holds the relic of St. Catherine’s head.
• In the evening, enjoy a delicious dinner of pici pasta paired with Chianti wine at a cozy trattoria before spending the night in Siena.

Today, drive to Volterra (approx. 1 hour and 35 minutes), with a memorable stop in San Gimignano along the way. You’ll be spending one night in Volterra.

Suggestion For The Day: 

• Stop first in San Gimignano, the Town of Fine Towers. Wander its medieval streets, try gelato at Dondoli in the main square, and climb the Torre Grossa for spectacular views.
• Continue to Volterra, a fascinating town with Etruscan, Roman, and medieval influences. Visit Piazza dei Priori, the Duomo, the Guarnacci Etruscan Museum, and the Roman Amphitheater.
• Volterra is famous for its alabaster craftsmanship - don’t miss browsing local shops for beautiful handmade pieces.

Drive from Volterra to Florence (approx. 1 hour and 30 minutes) where you’ll spend your final night in Tuscany.

Suggestion For The Day:

• Enjoy a leisurely morning exploring any spots you may have missed earlier in Florence, such as Mercato Centrale or the Oltrarno district, known for its artisans and charming cafés.
• For one last panoramic view, head to Piazzale Michelangelo, a perfect spot to say goodbye to Florence and the Tuscan hills.
• Conclude your adventure with a romantic farewell dinner in Florence, raising a glass to an unforgettable journey through the heart of Italy.