Tuscany Pre-Tour Extension (2025)

Upon arrival in Florence, you are met and transferred to your hotel where there is time to freshen up and relax. In the early evening, gather with your Resident Tour Director and fellow guests for a welcome briefing.

Castel Monastero

Drive through the Tuscan countryside to the historic enclave of Siena. Here, explore the rich legacy of the Palio, a spirited bi-annual horse race that’s pitted the city’s wards into passionate rival factions since 1444. After a tour of the city’s local museums, visit the site of the Palio itself, the storied Piazza del Campo; as well as the Palazzo Pubblico, home to Siena's Town Hall since the 1300s; and the city’s Duomo, one of Italy’s finest Gothic cathedrals. After lunch at a local restaurant, take some time to explore Siena on your own before returning to the hotel for some time at leisure. Later this evening, head to a local farmhouse for an authentic Tuscan dinner.

Castel Monastero | Meals: BLD

Today take in picture-postcard views of the Val d’Orcia from the 15th-century Tuscan town of Pienza. Explore this UNESCO World Heritage site renowned as a utopia of Renaissance planning. Then, pause for lunch at a local cheese producer celebrated for their pecorino. After lunch, return to the hotel for the remainder of the day at leisure.

Castel Monastero | Meals: BLD

After checkout, head into the Chianti countryside, taking in the rolling hills and fortified villas that witnessed fierce conflict throughout the Middle Ages. Pause for a stroll through narrow lanes of Radda, a historic town typical of the region. Then, visit a local winery for a tour of the cellars followed by four-course lunch at a wine estate in the heart of the Chianti Classico region. After lunch, transfer to Florence to meet your fellow Italy Cruise guests at The Westin Excelsior.

Meals: BLD