La Dolce Vita Wine Tours

Tuscan Trek

Walking the Wine Roads of San Gimignano and Montalcino

Itinerary:

DAY 1 – INTRODUCING BRUNELLO DI MONTALCINO

Welcome to our Tuscan wine & hiking tour. After a pick-up in Florence, we drive two hours south to Montalcino, our base for the next three days. We’ll drop off our bags at the hotel, then enjoy a complementary welcome lunch. If the sun is not too hot, we’ll eat al fresco, watching village life go by as we dine on Tuscan dishes like panzanella (bread salad) or homemade pici pasta with ragú.

Then, we embark on our warm-up hike: a loop heading down, then up the hill of Montalcino. Though relatively short (under two hours), you’ll work up a sweat, since Montalcino is Tuscany’s highest wine zone (680 meters).

Afterwards, we’ll again descend the north side of the hill by van in order to have our first winery visit, at Le Chiuse. The vineyard pedigree here is outstanding; this farm used to supply the legendary Biondi Santi with grapes for their Reserve Brunello (being distant cousins). Now the Magnelli family keeps everything for their own boutique label. Here we’ll enjoy the personal touch, as one of the family members will pour their excellent line-up.

Before dinner, we’ll meet on the hotel balcony for an introduction to Brunello di Montalcino, one of Italy’s most prestigious red wines, and its younger brother Rosso di Montalcino. Then we’ll enjoy the first of our gourmet wine dinners. We’ll be eating at a family-run restaurant that offers fabulous versions of traditional Tuscan fare, such as tagliatelle with porcini and truffles, pici with cherry tomatoes and garlic, and veal with balsamic juniper sauce.
L, D • Dei Capitani, in Montalcino

DAY 2 – GREGORIAN CHANTS & ASTROLOGICAL WINE

Today is a 12km point-to-point hike to the Abbey of Sant’ Antimo. Starting in Montalcino (the highest point), we’ll be ducking in and out of the woods, then walking on a gravel road along a long ridge flanked by meadows, with Monte Amiata visible in the distance. We’ll gradually descend into a valley where the 11th century abbey lies. We should arrive in time to hear the resident monks do their mid-day chants. Their plainsong goes perfectly with the spare white travertine and alabaster interior of the Lombard-style church, a popular destination for medieval pilgrims.

After lunch, it’s time to taste wine! We’ll sample some gorgeous Brunellos from Sesti, a small winery situated on a beautiful, historic property with a 10th century watchtower. The owner’s deep interest in astronomy and constellations is reflected in their gorgeous labels, as well as the winemakers’ decision-making in vineyard and cellar.

We’ll then shuttle back to Montalcino for free time to peruse the town’s wine shops or visit the fortress of Montalcino, which offers a fantastic view from its ramparts. We cap off the day at a cozy restaurant offering mouth-watering renditions of classic Tuscan cuisine, such as beef braised in Brunello wine.
B, D • Dei Capitani

DAY 3 – PIENZA’S PECORINO AND MONTEPULCIANO’S VINO NOBILE

This morning our first stop is Pienza, the center of pecorino production in Tuscany. The ability to make pecorino cheese was once considered a skill so valuable that women could list it on their dowry. We'll learn their secrets at a pecorino cheese shop, where we’ll taste samples of pecorino aged in various ways (wrapped in walnut leaves, olive paste, hay, or grape must, among other possibilities). Pienza is even more famous for its Renaissance architecture, commissioned in 1459 by Pope Pius II.

After visiting Pienza’s sublime, light-filled church, we’ll embark on our walk. This is a point-to-point hike, first to our lunch spot in Montechiello (7km), then continuing towards Montepulciano (potentially another 6km, depending on time & energy). We’ll be walking entirely on gravel roads, which trace the contours of rolling hills punctuated by tufa outcroppings, cypress trees, and footprints of wild boar.

In Montepulciano, we’ll try another of Tuscany's prized red DOCG wines: Vino Nobile di Montepulciano. Beloved by nobles, this was a favorite of Thomas Jefferson and Voltaire. We'll sample Vino Nobile and its younger sibling, Rosso di Montepulciano, at Icario, an up-and-coming winery. Its newly constructed cellar is an impressive piece of architecture, which also houses a galley for rotating art exhibits. Then it’s back to Montalcino for dinner on your own.
B • Dei Capitani

DAY 4 – THE ART OF SIENA

Today we take a break from hiking and visit to Siena during our transfer from Montalcino to San Gimignano. We'll start with a cappuccino at Nannini, Siena's most famous coffee bar. We’ll sample their panforte, a dense cake laden with nuts, dried fruits, and spices (a medieval power bar, in effect). We’ll then tour the Palazzo Pubblico, one of the most spectacular city halls in existence. Among its highlights are three masterpieces of Italian Gothic art: Simone Martini’s Maestá and Siege of Montemassi, and Ambrogio Lorenzetti’s Allegory of Good and Bad Government, the largest landscape since Roman times. We'll end up at Siena's striped cathedral, where you’ll have to option to visit artworks by Michelangelo, Pinturicchio, and Donatello.

Then you’re free for lunch, with time to shop or visit the Enoteca Nazionale, Italy's national wine museum/wine bar, located in a Medici fortress. Mid-afternoon, we continue our drive to San Gimignano. Still bristling with towers, it’s one of the most perfectly preserved medieval towns in Europe, earning it UNESCO World Heritage status.

Before dinner, we’ll have an informal tasting on the terrace of our hotel, a country villa and winery, offering an introduction to San Gimignano’s historic white wine, Vernaccia di San Gimignano. Dinner offers scrumptious updates of Tuscany’s woodland cuisine, based on wild boar (cinghiale), guinea fowl, and other game.
B, D • Pescille, in San Gimignano

DAY 5 – CIRCLING SAN GIMIGNANO

Today's morning hike partially encircles San Gimignano, offering great views of the town and vineyards around every turn—one of our most beautiful and varied hikes. Again, we’re mostly on gravel roads; there will be some ups and downs, along with long stretches of ridge. We’ll wind up back at the hotel for lunch in their gardens.

Then we’ll devote our energies to wine! Here we’re in ancient white-wine territory: Vernaccia has been produced here since the time of Dante. Today’s winery is Panizzi, a leader that produces six different renditions of Vernaccia, plus some excellent DOC reds. Then we'll visit the town of San Gimignano, paying a visit to the Collegiate Church, a medieval pilgrimage stop that contains a truly awesome floor-to-ceiling frescos.

Dinner is in town, where we'll be treated to regional specialties like garlic toasts (bruschette), peasant vegetable soup (ribollita), giant lasagna (pappardelle), and grilled meat. We'll learn the proper way to dip almond cookies (cantucci) in Vin Santo, a golden dessert wine first created by medieval monks.
B, D • Pescille

DAY 6 – WALK THE ETRUSCAN BYWAYS

Before Roman rule, Etruscans controlled Tuscany and planted its first vines. We’ll revisit this ancient civilization on our point-to-point morning hike to Volterra. This follows a country lane all the way, passing through various farms and woods. Flanked by ancient cypress trees, it offers glorious vistas of a landscape that shows traces of prehistoric floods.

In Volterra, there will be free time for lunch and for exploration of the hilltop town. Points of interest include a Roman amphitheater, an Etruscan city gate, and one of the best Etruscan museums in the world, which brings this sophisticated culture to life.

We then head back to San Gimignano for our afternoon wine tasting at Cesani, a small, family-run estate that produces a super Super Tuscan, as well as two excellent versions of Vernaccia. Our farewell dinner is in San Gimignano, allowing us to see the city in all its quiet magic at night.
B, D • Pescille

DAY 7 – BUON VIAGGIO!

A shuttle to Florence and assistance with your travel plans. B

Want a Tuscan wine tour without hiking? We can do that! See our Custom Tours page and contact us about a private, customized wine tour. Or join one of our non-hiking wine tours in Tuscany: the wine-intensive Xtreme Tuscany in the spring, or our classic Tuscan Wine Treasures throughout the year.

Please bear in mind that this itinerary is made one year in advance, so details may change due to the winemakers' schedule (especially during harvest), hotel availability, weather, and other unforeseen circumstances. Any substitutions will be with a property of equivalent interest and value.

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