Quintessential Tuscany: San Gimignano and Siena

Italy’s Best takes you to quintessential Tuscany on a private Siena & San Gimignano tour. View the rolling hills of Tuscany & these romantic hill top towns.


  • Visit the world-famous quintessential Tuscan towns of Siena and San Gimignano
  • See Siena’s most renowned sites, including Piazza del Campo, Palazzo Pubblico, the Duomo and the Museo dell’Opera
  • Enjoy a delicious typically Tuscan lunch at a local restaurant either in Siena or, according to your preferences, in the beautiful picturesque little town of Monteriggioni
  • Stroll through the winding cobblestone streets of San Gimignano at your own pace as you admire its 14 medieval towers and a stunning and unforgettable panoramic view of Chianti’s hills and valleys


Scenic Siena

The charming hilltop town of Siena is considered the quintessential Tuscan treasure by travelers the world over. During this lovely daytrip you will enjoy a leisurely stroll through the town, marveling along the way at its most famous sites, including the stunning main square, Piazza del Campo, home of the Palio, with its spectacular Palazzo Pubblico. The magnificent Duomo, a true architectural marvel with both Romanesque and Gothic influences, is also not to be missed. Depending on the time of the year, you may also be able to view the precious, world-famous floor mosaics at the Cathedral. Next, you will proceed to San Gimignano, where you will stroll through the utterly enchanting town’s winding cobblestone streets, stopping along the way to take in the glorious medieval beauty at your own pace.

Hilltop Marvel: San Gimignano Tour

No visit to Tuscany is complete without a San Gimignano tour! A perfectly preserved Medieval town with its walls and gates still intact, this hilltop “town of the 100 towers” offers a panoramic view of Chianti that overlooks Via Francigena, an ancient pilgrimage road between France and Rome. You may wish to visit the Collegiate Church of Santa Maria Assunta to see the 14th century frescoes of Old and New Testament stories and then to the Santa Fina Chapel which displays a fresco cycle from Florentine artist Ghirlandaio, a teacher of Michelangelo. The museum has a fascinating collection of Sienese art while the church of Sant’Agostino houses a Ghirlandio fresco cycle depicting the life of the church’s eponymous saint. Finish your visit atop the ancient walls to enjoy the view of the surrounding countryside. From San Gimignano, enjoy the ride back to your hotel while watching the unforgettable Tuscan landscape from the window of your Mercedes vehicle with the friendly English-speaking driver who will be your chauffeur for the day.