Day Trip to the Villages of Tuscany

Enjoy a guided exploration of Italy’s famed Tuscan villages. You’ll choose two towns to visit amongst the following: San Gimignano, Montalcino, Pienza, and Montepulciano. 

San Gimignano: One of the best-preserved medieval towns in Italy, San Gimignano sits perched atop an iconic hill. Located in the Elsa Valley, rich in cypresses, vineyards, and olive groves, the village produces Vernaccia di San Gimignano white wine with floral and fruity notes. However, San Gimignano is most famous for its encircling 13th-century walls, medieval plazas, churches, and stone towers that dominate the skyline. It's for these reasons that the town is a UNESCO World-Heritage Site.
  • Your local guide will take you along the main street, Via San Giovanni, where pilgrims and merchants once passed through as part of the Via Francigena route. Visit the main square, Piazza del Duomo (a religious and political center that houses the Town Hall and the Torre Grossa), and then walk to the green ‘hearth’ of the medieval town, the Poggio of Montestaffoli, where you’ll find the Fortress.
  • Delicious local saffron, Vernaccia wine, and gelato all await you after your tour ends! Be sure to pop in at one of San Gimignano's famous gelaterias, which have earned a reputation for producing some of the best gelatos in the world.
Montalcino. This fairytale hilltop town sits enveloped by the Val d'Orcia Natural Park, renowned worldwide for producing precious Brunello red wine. However, Montalcino is not just wine; it’s also very rich in artistic treasures. A mighty and imposing 14th-century Rocca (fortress) dominates the town center. You’ll enjoy spectacular views stretching toward Monte Amiata, Siena, the Valdorcia, and the hills of Maremma from the top. 
  • After meeting your local guide, explore Piazza Garibaldi, a central square with the small 11th-century Church of Sant'Egidio. Inside is the famous artwork of the Madonna and Saints by Luca di Tommé. Next, walk to the other end of the piazza, Costa del Municipio, which leads past the entrance to the Palazzo Comunale.
  • On the palace's exterior wall, you’ll find rows of oversized acrylic wine labels, and on the other side, a clock tower with an open corridor off the left side. At this piazza is the focal point of the evening passeggiata, the 19th-century cafe Fiaschetteria Italiana. It's the place where locals hang out after work and enjoy wine or an Aperitivo with snacks. You'll have time to taste Brunello or Rosso di Montalcino wine at the end of the tour.
Pienza. This town sits tucked into the stunning Val d'Orcia region of Tuscany. Pienza was the brainchild of Pope Pio II in the 15th century, intended to be a paradigm for perfect urban planning. Though construction halted after only a few years, traces of the great vision still stand. You’ll find crenulated church towers and shadowy arcades on Piazza Pio II. These signature pieces, along with the elegant loggias of Palazzo Piccolomini, earned the whole town a coveted UNESCO tag!
  • Enjoy your tour, stopping to see the magnificent Piazza Duomo (the cathedral's square overlooked by the beautiful Piccolomini palace). You'll follow the Via del Casello, which shows the most beautiful view of the Val d'Orcia. Walk along Corso Rossellino, the main street named after the Florentine architect who designed most buildings.
  • You'll notice the smell of Pecorino cheese and the green rolling countryside around Pienza. In the enveloping landscape, and from the terraces that line Pienza's hilltop spot, come views of the jaw-dropping Val d'Orcia. Either settle in for an espresso at one of the panoramic lookouts or hop between vineyards, cheese farms, and other ochre-stone villages nearby after your walking tour ends.
Montepulciano. With its many hills, green spaces, and magnificent views of the Val d'Orcia, Montepulciano is ideal for urban trekking. Your local guide will introduce you to the history, legends, and traditions of the Renaissance town that gave birth to Poliziano, a famed poet and tutor.
  • From Porta a Prato, you'll walk to the Church of Sant'Agostino along Via di Voltaia, where you'll find the main city buildings and enjoy the view of the Church of San Biagio from above. Continue uphill to the Piazza Grande, the political and religious center of Montepulciano.
  • Most people know Montepulciano for wine. Throughout the tour, your guide will talk about Nobile wine, and toward the end, you can visit one of the best cellars of Vino Nobile, dug under the soil of Montepulciano. This tour will leave you feeling fulfilled after two active hours of walking, discovering local products, and notable Tuscan architecture in Montepulciano.

Read more about unique and interesting activities in Tuscany.

Itineraries with Day Trip to the Villages of Tuscany

Italian Highlights from Rome to Cinque Terre - 8 Days

From artistic Florence to the famously beautiful National Park of Cinque Terre, this week-long highlights tour will give you a taste of some of the best that sunny, charming Italy has to offer. Explore Rome's ancient monuments, soak in the beauty of the Tuscan countryside, and visit vineyards, food shops, and incredible restaurants along the way.

Family Road Trip: Northern Lakes, Tuscany & Italian Riviera - 14 Days

Spend two weeks exploring northern Italy at your own speed with this self-drive itinerary that allows you to choose the stops. You'll start off in the northern lakes, with Lake Como and Lake Garda offering boat tours past villas and amusement parks alike. Then make your way into Tuscany, where you'll ride a horse-drawn wagon through the countryside and explore the medieval walled city of Siena and famous art of Florence. Finish your trip in the Italian Riviera and colorful five villages of Cinque Terre.

Explore Tuscany: Florence, Siena, Pisa, & Lucca - 8 Days

This packed 8-day itinerary is perfect for travelers on a time crunch. Begin your trip in Florence to see top Renaissance works by Michelangelo and da Vinci, tour the iconic Duomo, and go shopping on the Pontevecchio Bridge. Climb the leaning tower of Pisa and see the 12th-century Monumental Cemetery, then head to the countryside for wine tasting and afternoon coffee in medieval village piazzas. End in Lucca where you'll tour the 11th-century Duomo di San Martino, then make—and eat!—the perfect bowl of pasta. 

Tuscany Road Trip: Florence, Siena, & Montepulciano - 8 Days

This road trip around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.