Tuscan Wine Adventure


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.

6 Nights & 7 Days

Mixing it up with art and architecture from the Etruscans, Romans, Middle Ages, and Renaissance—all part of Tuscany’s endless allure. With its ancient abbeys, crenulated castles, olives groves, cypress lanes, and stone farmhouses, Tuscany lives up to its magical reputation. Hike through glorious landscapes around Montalcino and San Gimignano. Hear monks chant, taste fresh pecorino, glory in Renaissance art, and be wowed by Brunello and Vernaccia wine.

Available Attractions

San Gimignano

San Gimignano, with the impressive skyline of its medieval towers, stands on a hill overlooking the scenic countryside of the Elsa valley dotted with woodland, vineyards, and olive groves. 'San Gimignano delle belle Torri' is in Tuscany, 56 km south of Florence. It served as an important relay point for pilgrims travelling to or from Rome on the Via Francigena. The patrician families who controlled the town built around 72 tower-houses (some as high as 50 m) as symbols of their wealth and power. Now 14 remain, and, rising above Tuscany's Elsa Valley, they make the town look like a mediaeval dreamscape. The town also has several masterpieces of 14th- and 15th-century Italian art.


Montalcino, To the south of Siena is a classic fairytale hilltop town, set within a full circle of fortified walls and watched over by a mighty castle of medieval perfection. Montalcino, west of Pienza, is a beautiful village immersed in the breathtaking Val d'Orcia Natural Park, renowned all over the world for the production of its precious Brunello red wine. Montalcino produces a top-notch DOCG wine, Brunello di Montalcino, reckoned by many to be the finest in Italy, and is a quiet place, affluent in an unshowy way from its tourist trade. Montalcino is also a magnificent city of art which, from its hill, dominates the 3000 hectares of vineyards (1500 for Brunello) that have given it fame and wealth.

List of Not Included items for your package:

  • Visa on Arrival
  • Medical Insurance
  • Any meals not specified above
  • Any items of personal nature such as tips, Porterage, laundry, telephone bills, minibar etc.
  • Anything not mentioned in the “Inclusions column”
  • Optional Tours.
  • *Terms & Conditions Apply

    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 anintroduction 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.


    Today is a 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.


    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, then continuing towards Montepulciano. 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.


    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 atNannini, 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 andSiege 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.


    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 ofSan 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.


    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.

  • Day 7: BUON VIAGGIO!

    A shuttle to Florence and assistance with your travel plans.

  • *Terms & Conditions Apply


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