Tuscan Wine Treasures

A gourmet wine tour in Chianti Classico, Montalcino & Montepulciano

Tour Overview:

  • This Tuscan wine tour sportlights three historic wine zones: Chianti Classico in central Tuscany, and Montalcino and Montepulciano in southern Tuscany
  • Private sit-down tastings at Castello di Brolio, Castello dei Rampola, Ciacci Piccolomini d’Aragona, Icario & more
  • Visit the medieval Sant’ Antimo Abbey
  • Explore the Gothic city of Siena and its art treasures
  • Taste pecorino cheese in the Renaissance town of Pienza
  • Roll up your sleeves for a cooking lesson at a Chianti farmhouse
  • If you’ve never been in Italy, this tour is for you. When people dream of Italy, it’s Tuscany in their mind’s eye: rolling hills punctuated with slender cypresses, quaint stone farmhouses bordered by lavender and rosemary, tidy vineyards flanking dense forests that seem ready to burst with Renaissance falconers on horseback.

    It’s not a fiction. Tuscany’s wine country is situated in some of the most gorgeous, pastoral, and carefully preserved countryside on earth. Here you’ll find wines of equal splendor. Gone are the days of the straw fiasco. Tuscan winemakers are now among the most forward-thinking and iconoclastic of Italian enologists, and today’s Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano, and Super Tuscans are powerful, modern expressions that will surprise and delight even the most discerning wine drinkers.

    This tour covers two subregions within the ancient heart of Tuscany. We begin in Chianti Classico. Lying between Florence and Siena, this sprawling, forested land was contested by the rival city-states for nearly 400 years, and its fortified towns and storybook castles bespeak a history of warfare. We’ll visit the crenulated castle where Chianti was born and talk with winemakers whose bloodlines and properties go back to the 1100s.

    While in Chianti, we’ll also delve into Tuscany’s cucina povera during a cooking lesson in a rustic farmhouse kitchen. Prepare for fun! Even cooking-phobes who only boil water will be merrily whipping out ravioli and tiramisu before the night is over.

    The second half of the tour is in southern Tuscany. Barren of trees except for the lone cypresses that dot the brown hills (which inspired the color ‘burnt Siena’), this is far different from forested Chianti. A medieval feeling characterizes Siena, where we’ll have an art day, and Montalcino, our home base, as well as the Romanesque abbey of Sant’ Antimo, where we’ll listen to monks chant in an austere, spiritually resplendent environment. In contrast, the Renaissance architecture of Pienza, an “ideal” city built for Pope Pius II which today is brimming with pecorino cheese, will seem downright modern.

    Famous for its red wines since the time of Charlemagne, Montalcino is producing what’s widely considered Tuscany’s top wine: Brunello di Montalcino. Meanwhile, economy-minded wine enthusiasts will appreciate our time in Montepulciano, whose Vino Nobile has found fans as far back as Thomas Jefferson and Voltaire.

    Altogether this tour provides an excellent overview of the great historic red-wine zones of Tuscany and their centerpiece grape, sangiovese. With its judicious mix of art, culture, and culinary sidelights, this will truly be your dream vacation!


Dispatches from the wine road
– Livin' La Dolce Vita


National Geographic Traveler
– See our award-winning trips


News, tips, recipes every month
– Sign up today