Tuscan wine Trek

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.



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.
L, D • Dei Capitani


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.
B, D • Dei Capitani


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.
B • Dei Capitani


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.
B, D • Pescille


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.
B, D • Pescille


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


A shuttle to Florence and assistance with your travel plans. 

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.

Hiking Level of Difficulty

This is one of our easiest hiking tours, for two reasons. First, there’s a support van that accompanies us every day, so you can jump in the van if you get tired. Second, for the majority of the time, we’re walking on gravel country roads. That means there’s no tricky scrambling on rocky trails, no mountain steps, hardly any hilly vineyards, and just an occasional dirt path in the woods. But there are hills (this is Italy, after all), including a couple of steep ones. But as we say, piano piano, take your time, and you’ll be at the top before you know it. Be prepared to walk 3 to 4 hours every day, except the shorter warm-up hike on Day 1. That’ll let you enjoy an extra gelato guilt-free!


Florence or Pisa (continental), or Rome (intercontinental nonstop). To land in Florence or Pisa, you’ll need to connect somewhere in Europe. From the Florence airport to the city center, it’s a 20-minute taxi ride. If arriving in Pisa, the airport has its own train stop and is only an hour from Florence. Rome is the closest intercontinental airport, with direct flights to the US. If arriving in Rome, you’ll need to take a train from the airport to town (30 min.). Then from Rome’s main train station, it’s only 95 minutes to Florence on the fast train (EuroStar); the latter requires reservations.


Plan to land in Italy at least a day before the tour begins; that’s necessary to be at our starting point on time. Most people spend the preceding night in Florence. For hotel suggestions, email us or consult a good hotel search engine, such as TripAdvisor or Venere. If you’re spending just one night, we recommend staying near the main train station, Stazione Santa Maria Maggiore, since that is our meeting point. Otherwise, take your pick of neighborhoods. Florence is not a huge city, and it’s very walkable. In fact, we encourage you to get out and walk around; the streets are a living museum!

Meeting point

Our meeting point is Florence, at the main train station, Santa Maria Novella (details will be indicated in your information packet). From here, we shuttle to Chianti (about 1 hour), where the tour gets underway. (We cannot pick up from individual hotels because only taxis and permanent residents are allowed in Florence’s city center.)

Departure day

On our final day, we’ll have you back at the Florence train station by noon.

Italian train schedule

Click here for the Trenitalia schedule in English. Be aware that the schedule is posted only several months in advance, so if you’re looking for long-range dates, try something sooner, just to get an idea of departure frequency and trip length.

Trip extensions

Because TUSCAN TREK does not include any time in Florence, we recommend spending a few days in this fabulous art city, either before or after our tour. Florence is easy to navigate on your own. But there are also excellent thematic walking tours offered by our friends at ContextTravel. If you’d like to explore other small-sized cities in Tuscany, Florence is well connected with Lucca (1 hr, 20 min) and Arezzo (1 hr) by train. And it’s just a hop and a skip to Rome on the EuroStar express train (1 hr 35 min).


When packing, check check www.weather.com. Go to “San Gimignano, Italy” and “Montalcino, Italy” to get a general idea of temperatures and forecast. By mid-June, we’ll be experiencing nice summer weather, with daytime temperatures averaging 80º and nighttime dipping back to 60º. In October, fall weather has commenced. Daytime temps average 60º and nighttime 47º, with a chance of sporadic showers.

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