Villages of Tuscany - Small Group

Arrive in Rome, a capital built on the legacy of the ancient empire and the power of the papacy, then meet your Travel Director before heading out on an orientation. You’ll see the Roman Forum, where public life once unfolded in the heart of ancient Rome, and the Trevi Fountain, a Baroque landmark that shows a later chapter of the city at full scale. This evening, sit down to dinner with your fellow travelers as historic Rome sets the scene for the journey ahead.

Travel to Orvieto and ride the funicular up to its hilltop old town, where your Travel Director introduces you to this Umbrian city of volcanic stone, cathedral facades and streets built high above the valley below. Take time to explore at your own pace and find somewhere local for lunch. Continue through Tuscany’s wine region, a landscape shaped by vineyards and long-standing wine traditions, before arriving in Montepulciano for an orientation of the village with your Travel Director. Later, you’ll enjoy a tasting of local wines and discover the character of one of Italy’s best-known wine regions.

Spend the day in two of southern Tuscany’s best-known hilltop towns. In Montalcino, join your Travel Director for an orientation, then take time to explore and pause for a cappuccino with views over the Val d’Orcia. Continue to Pienza, the Renaissance town created under Pope Pius II, where your Travel Director introduces the layout and history of this UNESCO-listed center. Then taste the pecorino cheese the town is known for before free time for lunch. Later, return to Montepulciano, where the evening is yours to relax or head out with your small group for a plate of pici all’aglione in town.

Drive through the Tuscan countryside to Siena, a medieval city best known for the shell-shaped Piazza del Campo and its Gothic Duomo. Spend time at the Mercato delle Merci, one of Tuscany’s biggest weekly markets, where locals come to shop for everything from food to everyday goods. Browse the stalls, step into Siena’s small stores and perhaps try panforte, the dense fruit and nut cake closely tied to the city. Later, join your Local Specialist to explore Siena’s historic districts, see the Piazza del Campo and Duomo, and visit a contrada museum.

Start in Certaldo, where your Travel Director introduces a hill town with strong medieval roots in the heart of Val d’Elsa. You’ll have time to walk the walls, look out across Chianti and perhaps settle into the square for a cappuccino before exploring the shops and museums. Continue to San Gimignano, the UNESCO-listed town that rose to prominence on the Via Francigena pilgrimage route and is still known for its skyline of medieval towers. Later, head into the Tuscan countryside for your Be My Guest experience at a local agriturismo, where wine, history and local culture come together.

Head to Volterra with your Travel Director to explore a hill town known for its Etruscan roots and medieval streets. In the historic center, see the Roman Theater, the Cathedral and the Palazzo dei Priori, the oldest town hall in Tuscany. You’ll also get to witness the ancient local tradition of alabaster sculpting, one of Volterra’s best-known crafts, and for which the town is still renowned today.

Enjoy a slow start in Volterra, with the morning free to explore more of the town at your own pace. Then head south to the Abbey of San Galgano, where the roofless church and monastic ruins make a striking stop in the Tuscan countryside. Continue to Grosseto, a walled city in southern Tuscany, for an orientation with your Travel Director. As you get your bearings, see the layout and landmarks of a historic center shaped by Medici rule and still enclosed by its star-shaped walls.