Tuscan Trek

Walking the Wine Roads of San Gimignano and Montalcino

Tour Overview:

  • Hike in two distinctive subregions of Tuscany: Montalcino and San Gimignano
  • Enjoy private, sit-down tastings of Brunello (Le Chiuse, Sesti), Vino Nobile (Icario), and Vernaccia (Cesani, Panizzi)
  • Visit the Etruscan town of Volterra
  • See the Renaissance splendor of Montepulciano
  • Taste pecorino cheese in Pienza
  • Hear Gregorian chants at the medieval abbey of Sant’ Antimo
  • When you dream of picture-postcard Italy, this is it. The Val d’Orcia, deemed a UNESCO World Heritage site, has those rows of slender cypress trees marching along crests of stark, undulating hills, like a Piero della Francesca painting. It has the lavender and rosemary hedges, the climbing jasmine, and the bright yellow broom perfuming the landscape. It has the immaculate stone farmhouses with rosebushes, the ancient abbeys, and the fortified cities with medieval towers and encircling walls.

    These are the landscapes of TUSCAN TREK. This hiking tour covers two distinct sub-zones: southern Tuscany—including Montalcino, Montepulciano, and Pienza—which is where you’ll find the barren hills, burnt Siena colors, and lonely cypresses seen in so many photographs. And San Gimignano in central Tuscany, a wooded area, where it feels like a knight on horseback might pop out of the forest at any moment, hunting with his falcon.

    The tour is structured with morning hikes and afternoon wine tastings. We hike every day except one, when we transfer regions and stop in the Gothic city of Siena. Most hikes are approximately three to four hours (7 to 10 miles) along country roads and trails (see Trip Notes); there’s van support every day.

    By mid-afternoon, we’re heading to the wineries by van. Here the spotlight is on Brunello di Montalcino, Tuscany’s most esteemed, age-worthy red wine, and Vernaccia di San Gimignano, a white served in medieval wine bars to pilgrims walking to the Holy Land, which is mentioned (with a finger wag) in Dante’s Inferno.

    We’ll be mixing it up with art and architecture from the Etruscans, Romans, Middle Ages, and Renaissance—all part of Tuscany’s endless allure. We’ll time travel to the 1100s when we listen to plainsong chants in the Abbey of Sant’ Antimo or walk the back streets of San Gimignano, another UNESCO site—and deservedly so. After the Black Plague devastated the city in 1348, San Gimignano was frozen in time, abandoned and bypassed for centuries. As a result, it has remained one of Europe’s best-preserved medieval towns. A dream setting for a dream vacation.

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