Tuscany Dream Self-Drive - First Class Hotels

Pick up your rental car in Florence and drive into the beautiful Chianti countryside (approx. 1 hr). Stop in Radda in Chianti, once headquarters of the Chianti League, and explore its medieval streets, historic Palazzo del Podestà and local enotecas. Continue to Castellina in Chianti or Greve for lunch before travelling towards Siena. En route, consider a stop at Monteriggioni, a remarkably preserved 13th-century fortified village surrounded by medieval walls and towers. Overnight in the Siena area.

Drive to San Gimignano (approx. 45 min), famous for its medieval towers and UNESCO-listed historic centre. Wander through its atmospheric streets and Piazza del Duomo before returning to Siena. Spend time exploring Siena’s magnificent historic centre, including Piazza del Campo and its impressive Cathedral. Perhaps sample some local specialities such as pici pasta and panforte along the way. Overnight in the Siena area. Additional local experiences to choose from: Siena Cathedral Ticket & Pastries and Cantuccini tasting in Siena. (B)

Today explore the distinctive landscapes of the Crete Senesi, with rolling clay hills, cypress-lined roads and isolated farmhouses. Travel towards Asciano, with the option to visit Monte Oliveto Maggiore Abbey, before continuing through the countryside to San Galgano Abbey. Discover the impressive roofless Gothic abbey and nearby Hermitage of Montesiepi, home to the legendary Sword in the Stone. Return to the Siena for overnight. Additional local experience to choose from: San Galgano Abbey Ticket . (B)

Leave Siena and travel into the UNESCO-listed landscapes of the Val d'Orcia. Visit Pienza, the Renaissance town renowned for its beautiful historic centre and Pecorino cheese. Continue to Bagno Vignoni, an unusual village where the main piazza is occupied by a large thermal-water pool. Take time to wander through the village and perhaps follow the Parco dei Mulini trail before continuing to your hotel. Overnight in the Val d'Orcia area. Additional local experience to choose from: Pienza cheese tasting. (B)

Drive to Montalcino, the hilltop town famous for Brunello di Montalcino wine and dominated by its medieval fortress. Explore the town and perhaps visit nearby Sant'Antimo Abbey before continuing to Montepulciano. Wander through its historic streets to Piazza Grande and discover the wine cellars carved beneath the town, home to the celebrated Vino Nobile di Montepulciano. Overnight in the Val d'Orcia area. Additional local experience to choose from: Wine & Food tasting in Montepulciano. (B)

Enjoy another day exploring the beautiful Val d'Orcia countryside. Discover some of the area's smaller historic villages, including Castiglione d'Orcia and San Quirico d'Orcia, with its Renaissance Horti Leonini gardens. Continue at your own pace through the surrounding countryside, perhaps revisiting Bagno Vignoni or travelling towards the fortress town of Radicofani. Overnight in the Val d'Orcia area. (B)

Depart Val d'Orcia and drive back to Florence (approx. 2 hrs). Depending on your schedule, stop in one of Tuscany's smaller towns such as Buonconvento or Murlo for a final taste of the countryside. Continue to Florence and return your rental car, where your arrangements conclude. (B)