Arrival. In the afternoon meet your local guide for a private guided walking tour of this town rich in history, art and popular traditions. Possibly the best preserved medieval city in Italy, Siena is built on three hills and full of winding alleyways, enclosed within the circle of its massive walls. Overnight.

Breakfast. Full day excursion to Pienza and Montalcino. Enjoy a winery visit and tasting at Fattoria dei Barbi followed by a lunch at the Taverna. After lunch continue to Pienza, an elegant Renaissance town, built on a hill that dominates the Val d’Orcia. Pienza is listed as a UNESCO World Heritage site since 1996 for its important example of Renaissance urban planning, architecture and monuments. Meet your local guide for a guided walking tour. Top off the day with a visit to a ceramic laboratory and shop. Return to Siena and overnight.

Breakfast. Today the tour will take you to San Gimignano. The town is recognized as a UNESCO World Heritage Site since 1990 and offers you the chance to step back in time. Discover this small walled village on a private guided tour, famous for its fascinating medieval architecture and towers. At the height of its glory, San Gimignano's patrician families had built around 72 tower-houses as symbols of their wealth and power. Although only 14 have survived, San Gimignano still retains its feudal atmosphere and appearance. Lunch in a local restaurant. On your way back to Siena, enjoy a winery visit and tasting. Overnight.