Walk the wine roads of Montalcino & San Gimignano

  • Morning hikes in two distinctive subregions: Montalcino & San Gimignano

  • Afternoon wine tastings of Brunello, Vino Nobile, and Vernaccia

  • Visit the Etruscan town of Volterra

  • See the Renaissance splendor of Montepulciano

  • Taste pecorino cheese in Pienza

  • Contemplate the medieval abbey of Sant’ Antimo



Welcome to our wine + walking tour in Tuscany’s Montalcino and San Gimignano wine zones. 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


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, founded by Charlemagne. With a spare white travertine and alabaster interior, this Lombard-style church was a popular destination for medieval pilgrims on the Via Franciagina.

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


Today’s first stop is Pienza, 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


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


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


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. B

Want a Tuscan wine tour without the hiking? We can do that! Join the wine-intensive Xtreme Tuscany or our classic Tuscan Wine Treasures.


Hiking level of difficulty
We consider this 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, and just an occasional dirt path in the woods. There are hills (this is Italy, after all). 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. 

Italian train schedule
Here's the English-language version of TrenItalia. 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.

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 Novella, 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.

Trip extensions
Because this tour 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).

Travel insurance
This is recommended to protect you from needless loss caused by last-minute cancellations, lost luggage, and more. Three sources are Travelex Insurance, (800) 228-9792; CSA Travel Protection, (800) 348-9505; and Travel Guard, (800) 826-1300.

When packing, check Go to “Montalcino, Italy” and “San Gimignano, Italy” to get a general idea of temperatures and forecast.

For cancellation policy & more, see our General Information page.

2019 dates
For private, custom groups only
Minimum group size: 4
Contact us to pick dates

Single supplement: $400
Price based on the accompanying 7-day itinerary for 4 pax, double occupancy; discounts for larger groups. Modifications are possible, including length of tour, daily mileage, level of accommodations, amount of wine tastings, and inclusion of meals.

Meet & depart
Florence train station

What's included
- 6 nights accommodations (double room) in two 3-star hotels, with breakfast buffet
- 5 gourmet dinners (three courses with wine)
- 1 welcome lunch
- All wine tastings mentioned
- Admission to Siena's Palazzo Pubblico, San Gimignano's Collegiata church

What's not included
- Air travel
- 1 dinner on your own & all lunches
- After-dinner drinks, or special wines at tastings that are not part of what is provided to the group
- Bike and helmet rental
- Items of a personal nature
- Anything not specified as included

All my favorite activities in one package: hiking scenic countrysides, sampling local foods, and drinking good wine. We made new friends, ate and drank extremely well, and discovered parts of Tuscany we would never have found on our own.
— Lauren Kolb, Farmington, CT