Day Trips from Siena to Pienza

Taste your way through Tuscany with this full-day wine tour of Pienza and Montepulciano from Siena. Visit the charming town of Pienza and stop for one wine tasting each in Montepulciano. You also enjoy plenty of free time to explore each village on your own.

Discover Tuscany's stunning landscape, culinary delights and UNESCO-listed sites on a day trip to Montepulciano and Pienza from Siena. Led by a local guide, admire the architectural gems of the Val d'Orcia region and stop at a dairy farm for lunch and samples of salty Pecorino cheese. Conclude your trip in the scenic hill town of Montepulciano, with an optional visit to a winery. Group size is limited to eight people, ensuring personalized attention from your guide.

Explore Tuscany beyond Florence or Siena with a full-day wine tour. Get picked up at your hotel for a small-group tour to visit local wineries and relax over lunch in the town of Montepulciano. Learn about how wine is made and taste regional specialties including Brunello. Meet the people behind the wine without the hassle of a rental car or navigating between wineries.

Experience the best of Tuscany—cheese and wine, of course!—on this private tour from Siena. You’ll admire fabulous scenery in the Val d’Orcia, learn about cheese making during a tour at an organic dairy farm, visit the World Heritage–listed town of Pienza, and enjoy tastings of the region’s renowned Brunello wine during a cellar tour at a winery in the hilltop town of Montalcino. With a privately guided tour, enjoy a more personalized experience.

Surround yourself with the unrivaled scenery of Valle de Orcia while trying some of its epicurean delights on a private day tour from Siena. Begin in the hill town of Montalcino, where you'll sip on locally-produced wine at a popular winery. Later, head to the historic center of UNESCO-listed Pienza, where you'll enjoy free time to explore independently. A typical Tuscan lunch and cheese tasting also accompany the immersive experience.