The 8 Best Montalcino Wine Tours of 2021

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The sunny, dry hills surrounding the tiny Tuscan town of Montalcino produce some of the world’s finest Sangiovese grapes, which local producers have been carefully crafting into Brunello di Montalcino for centuries. This wine is one of the world’s most exclusive (and expensive), and seeing the process up close brings serious oenophiles and casual wine-lovers from around the world to visit Montalcino’s many beautiful wineries.

As with any winery tasting trip, it’s always more fun to do your visits with the help of some sort of designated driver, so you can taste to your heart’s content. For English-speakers visiting the Montalcino region, a guided tour also helps with the language barrier, and a good tour guide can be invaluable for planning an itinerary that allows you to really get a sense for the history and wine culture of the area. Take a look below to see what we think is the best of Montalcino’s many wine tour options.

Best Budget Tour: Montalcino, Pienza, and Montepulciano Wine Tour

Montalcino vineyards

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Believe it or not, it’s very possible to get a good look (and taste) of this legendary wine region without breaking the bank (or needing to designate a driver), and this tour is a great place to start. It’s a bus tour that departs from a central meeting point in Florence and does include a tour guide (tours are conducted in English).

You’ll start your day at a winery in Montalcino, where you’ll enjoy a winery tour that includes a wine tasting and some snacks. From there, you’ll enjoy touring the medieval town of Montalcino itself, where you’ll have a bit of free time to sightsee. The day continues with two more largely-unguided stops: one in the culinarily-famous town of Pienza, where you can enjoy lunch (own expense) and one in the handsome Renaissance town of Montepulciano. It’s a great way to see a lot of the area while also having ample opportunity to taste the region’s wines while also staying within a budget.

Best Biodynamic Winery Tour: Brunello di Montalcino, Small Biodynamic Wineries

Brunello di Montalcino

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Biodynamic production is increasingly popular among Italy’s wineries and, indeed, wineries around the world. This production technique goes beyond organic farming practices and includes everything from ultra-traditional folk techniques (like planting based on moon phases) to rather new-agey approaches (some farmers, for example, play specific types of music to their growing crops). Whether or not you necessarily agree with the approach (experts are quite divided), there’s no question that the tender, highly-individualized care with which biodynamic producers treat their products results in something special.

This small-group tour, which departs from and returns to a central meeting point in Florence, explores two different biodynamic Montalcino wineries. You’ll have lots of time to see the facilities and learn about the biodynamic processes, and naturally, you’ll get to taste lots of wine and other products. The tour includes a Tuscan lunch as well as snacks throughout the day, and between winery visits, you’ll enjoy a quick guided tour of the town of Montalcino itself.

Best Private Tour: Top Brunello di Montalcino Wine Tour

Top Brunello di Montalcino Wine Tour

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There’s so much to be said for booking a private tour: You get personalized attention from your guide, so you can ask all the questions you want all day long, and you also have tremendous flexibility in your itinerary. Having a great time in one place? Great, stay longer. Want to hurry along? No problem. There’s no one to wait for or to rush you along — it’s your day.

This wonderful private tour combines all that flexibility and personalized attention with serious insider knowledge of the Montalcino region and its best wineries and wines. The day begins with a pickup from your Siena or Florence hotel and departs on a suggested itinerary that includes three winery stops, accompanied by your professional sommelier guide.

Throughout the day, you’ll visit cellars and vineyards along with tasting rooms and get to meet some of the master vintners and winery owners at the places you visit. You’ll also enjoy a traditional homemade Tuscan lunch paired with a selection of wines and accompanied by a lesson from your sommelier-guide about traditional regional wine pairing techniques.

As a special treat, the tour includes an olive oil tasting at one of the wineries, as well. Your wine-filled day ends with a trip back to your Florence or Siena lodgings (no one will blame you if you nap on the way). 

Best Tour from Rome: Montalcino and Pienza Tour from Rome

Montalcino countryside

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Rome’s a bit further-flung than Florence or even Pisa (it’s about 2.5 hours by car), but visitors to Rome should absolutely consider a wine-tasting day in Montalcino/Tuscany — it’s beautiful and the wine is second-to-none, so why not? This tour includes private luxury transport from Rome to Montalcino with a driver/guide who’ll take you first to a winery in Montalcino to begin your day with the hearty Brunello di Montalcino.

From there, you’ll make a quick visit to the town of Montalcino and then on to Pienza to taste the crumbly, nutty local sheep’s milk cheese. After, you’ll head to the world-renowned Poliziano winery in Montepulciano to taste Vino Nobile di Montepulciano and learn a bit about what makes this wine different from that of Montalcino. This is a private tour, so you have quite a bit of flexibility — if you’d prefer to taste more and sightsee less, that’s definitely doable, and vice versa. 

Best Tour from Pisa: Enogastronomic Tour of Montalcino, Pienza & Montepulciano

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Foodies on a short timetable, look lively: this is the perfect tour for you. The day begins with a trip from Pisa to Florence, from which you depart to head into the Tuscan hills, with Montalcino first on the docket. You’ll visit one of the region’s best cellars for a Brunello di Montalcino tasting alongside a snack consisting of local specialties.

From there, you’ll head into Montalcino proper for a quick tour, and then it’s on to architectural gem Pienza, where you’ll dig into the prized local cheese, Pecorino di Pienza. This pecorino (a dry sheep’s milk cheese) isn’t as famous as the Roman counterpart, but it is equally as delicious and a real treat to taste in its place of origin. The tour’s final stop is at a Montepulciano winery, where you’ll taste the rich red Vino Nobile di Montepulciano before heading back to Pisa via Florence. 

Best Tour from Siena: Small-Group Brunello di Montalcino Wine-Tasting Trip

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

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It’s a rare visitor to Siena who doesn’t have “visit Tuscan wineries” on their must-do list while they’re in the area, and if that sounds like you, consider this wonderful small-group tour. Your first stop will be at a small winery, where you’ll visit both the vineyards and the cellars with your expert guide, and get your first taste of the famous Brunello di Montalcino.

From there, you’ll head into the town of Montalcino itself for some free time to explore, nibble, or shop to your heart’s content. As lunch rolls around, you’ll head to a local family-run winery, where you’ll meet the winemakers and enjoy a three-course traditional-style lunch complete with wine pairings. Walk lunch off on the grounds of the ancient Benedictine Abbey of Sant’Antimo as your guide shows you around and explains the historical significance of this extraordinary place.

Finally, stop at a third winery, where you’ll learn about contemporary production and aging processes and get a final taste before heading back to Florence. It’s a nice full day that includes both guided tastings and some free time for a good overall balance.

Best Connoisseur’s Tour: Brunello and Nobile Wine Lovers’ Tour

Montalcino grapes


For wine lovers who already pretty well know their stuff, sometimes traditional tours can be a bit tedious. There’s no shame in wanting to go deep and get a bit nerdy, and if that’s your goal, this is the tour for you. It’s a private tour that departs from and returns to your lodgings in Florence (note that the price is per group, not per person) and gives you the full attention of a sommelier guide throughout the packed day of wine-tasting.

The tour includes two in-depth winery stops: one in Montalcino and one in Montepulciano. Hard-core oenophiles know that these two tiny Tuscan regions have a bit of a friendly (and ancient) rivalry between them, and you’ll enjoy comparing and contrasting their superstar wines: Brunello di Montalcino and Vino Nobile di Montepulciano. The former is made from 100 percent Sangiovese grapes, whereas the latter contains up to 30 percent Canailo Nero and other specialized local varietals. What fun, tasting them both, picking up hints of their ever-so-slightly-different terroirs, and getting the inside scoop from your guide and your winery hosts. All that, plus one of the most gorgeous off-the-beaten-path drives through Tuscan hills — it can’t be beaten.

Best Luxury Tour: Luxury Montalcino Wine Tour


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You’ve come all the way to Tuscany, why not consider going all-in on a top-of-the-line luxury tour? This private tour departs from your accommodations in Florence and whisks you away in air-conditioned luxury to the hills of Montalcino. Your first stop of the day will be at Podere Le Ripi, an organic-certified biodynamic winery where you’ll have a private tour that explains the biodynamic winemaking process. You’ll enjoy a three-course gourmet lunch prepared by Michelin starred chef Massimo Rossi while sitting on a quiet terrace overlooking rolling, vine-covered hills stretching into the distance. Naturally, the meal will be paired with the estate’s finest wines. Your second stop will be at Castel Giocondo, a property that has been in the same family for nearly 1,000 years. You’ll taste more wines and learn about the history of the region’s viticulture while enjoying one of the best views in the region. At the end of the day, you’ll be delivered back to your Florence lodgings in comfort.

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