Day Trip from Rome to Tuscany

01Experience a day trip from Rome to the beautiful Italian region of Tuscany with a private driver! Explore medieval little towns such as San Gimignano, famous for its unique architecture and medieval towers, and Monteriggioni, an ancient fortress where time seems to stand still. Visit the lovely historic center of Siena and enjoy a sightseeing around the picturesque Orcia Valley.


The city of Siena

Your private, English-speaking driver will pick you up directly at your hotel in Rome at 7:30 in the morning. Travel comfortably by private car and listen to interesting facts about Italian history and culture your driver will tell you during your trip to Tuscany.

Upon arrival in Siena, begin your visit with a stroll through the alleyways of the medieval town! Afterwards, head to Piazza del Campo, the unique shell-shaped square, which is the old political center of Siena and also hosts the worldwide famous, Palio.

Medieval Towns: San Gimignano and Monteriggioni

Next, head to the medieval towns of San Gimignano and Monteriggioni, two gems of Siena’s surroundings! Follow your knowledgeable, entertaining driver through the cobblestone little alleys of San Gimignano, a UNESCO world heritage site since 1990. Admire the characteristic towers built by the most noble and richest families of San Gimignano as symbol of their power and influence.

Then, reach the medieval town of Monteriggioni. This fortified village, which still survives the test of time, was also mentioned by Dante Alighieri in his famous masterpiece “La Divina Commedia”. Marvel at the well-preserved historic city center surrounded by the original town walls, featuring fourteen towers and two major doors.

Sightseeing and Lunch in the Tuscany countryside

End your driving tour in Tuscany with an enjoyable sightseeing of the famous Orcia Valley!
Absolute protagonist of this impressive valley, located in southern Tuscany, is nature. The whole area is indeed a protected natural park, crossed by the Orcia River which flows through untouched valleys and hills. This land also gave origin to some of the finest Italian wines such as the “Brunello di Montalcino” and the “Nobile di Montepulciano”. Enjoy the view of this astonishing landscape, studded with medieval towns and abbeys, which inspired many Renaissance painters!

Then, within the surreal atmosphere of Val d’Orcia, stop for lunch in a typical trattoria, where you will have the chance to taste local recipes and wines before heading back to your hotel in Rome.

Wine tasting

Upon request, it is also possible to arrange wine tastings in some of the finest wine cellars in the area. You will then have the opportunity to taste a variety of regional, award winnings wines which have made this area famous all over the world.


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© 2016 When in Italy, a team of young licensed and experienced tour guides and English-speaking drivers specialized over the years in offering customized private tours.


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