Private Brunello Wine Tour

Together with the Chianti Classico, the Val d’Orcia National Park makes up the heartland of Tuscany’s world-renowned wine region. And if the wine is not enough of a draw, there is stunning scenery to boot—from hilltop towns to harmonious landscapes.

Combine your love of travel with an immersive celebration of Italy’s most lauded wines. This private excursion to Val d’Orcia, south of Siena, famous as the Brunello wine area blends art, history, and picturesque landscapes with carefully selected wineries to enjoy.

Val d’Orcia, Tuscany

Recently added to the prestigious list of UNESCO World Heritage Sites for the unmatched beauty of its landscapes, the Val d’Orcia Valley is a gem of pure Tuscan charm. Its DOC wine is as smooth as the sloping hills that stretch as far as the eye can see.

The art city of Siena is very close to here. Whether you are a wine novice or aficionado, or just want to take in the beautiful scenery, a day trip should be on every visitor’s to-do list.

Brunello di Montalcino DOCG

One of the most ancient, appreciated and awarded wines of the whole world. The Brunello wine is produced only in the strikingly beautiful countryside surrounding the medieval town of Montalcino, south of Siena. Discover many typical products of a territory that really shines for wine&food culture. 

Nobile di Montepulciano DOCG

Montepulciano is called the “pearl of the 1500s” thanks to the many works of art by famous Renaissance artists gathered within its walls. As a work of art of modern times, Montepulciano’s Nobile is considered one of the greatest red wines produced in Tuscany. 

Wine Tasting in Montalcino and Montepulciano

We select the best wineries creating unique itineraries that will lead you through the secret and fascinating world of taste. In the amazing landscapes of Val d’Orcia, you will visit Montalcino well known for its Brunello wine and Montepulciano famous for its Vino Nobile wines. In both charming hilltop towns, wine lovers will find themselves in paradise!

This specially curated wine tasting itinerary will take you to our favorite wineries allowing you to savor the best of wine harvests and learn all about wine making traditions, wine varieties, and the art of wine pairing from local winemakers happy to welcome you.

Stop in the town of Pienza, a true gem of Renaissance architecture

On top of incredible wines and scenery, the hilltop town of Pienza, nestled between Montalcino and Montepulciano boasts artistic and cultural gems, making this destination an essential stop on a Tuscany itinerary. Set in Val D’Orcia Tuscany’s most pristine corner, Pienza, offers a rare example of a Renaissance ideal town untouched by time, but that is just one of its strengths!

This perfectly preserved Renaissance town famously features a series of streets with romantic names like Love Street and Kiss Street. And best of all, it is home to Pecorino the most popular Tuscan cheese and there are ample opportunities to sample a delicious variety of options.

Wine Country with Kids

The Val d’Orcia valley known for its exquisite wines and stunning natural beauty is a haven for honeymoons, vinous vacations, and older crowd. Just because you are visiting vineyards it does not mean you have to rule out a traditional wine tasting experience since we have carefully chosen a broad range of family-friendly wineries where kid visitors receive a warm welcome.

As you start planning your next family escape, do not cross this region of Tuscany off your list as a kid-friendly option. At Nancy Aiello Tours, we know that the Val D’Orcia has something special to offer everyone in your family, including its littlest members. So, do not be afraid to take your whole clan along, they might just have as much fun as you do! And if you have teenagers over the age of 16, you might want to consider allowing them to taste a few wines. The drinking age in Italy is 16, not 21 like in the United States, so it is legal.

Wine and Beyond

A wine country tour in Tuscany is one of the best ways to discover the true essence of the region. Departing from and returning to your Florence or Siena hotel, you will taste top-rated regional varietals in Montalcino and Montepulciano, explore the Renaissance heart of Pienza, and admire the villages scattered across the breathtaking countryside.

Best of all, your expert driver-guide looks after you to provide even more insights, recommendations, and connections, and to ensure an exquisite experience in the heart of Tuscany!

What To Expect

Most likely, the day will be 1.5-hour drive from Florence or 50 minutes’ drive from Siena to the first winery in Montalcino, stop in Pienza famous for its typical Pecorino sheep’s milk cheese, and second winery visit in Montepulciano. If wine tasting, scenic drives, and artisanal food are your thing, then this is the trip for you.

On this Montalcino, Pienza, and Montepulciano private Tuscany wine tour, you will enjoy a beautiful tailored itinerary built around your needs including pick up location, length of tour, types of wineries and tasting experiences, all backed by our in-depth first-hand experiences and knowledge.


Enjoy from the comfort of your own air-conditioned vehicle, a scenic drive with the luxury of stopping off to take photos. As you journey to your first wine tasting destination, your driver-guide will fill you in on the Tuscan wines and hot spots. The hilly town of Montalcino is not just home to celebrated Brunello wine, it is also a fairy-tale place blessed with amazing history and culture.

Montalcino historical center is well preserved and it is famous for its imposing 14th century fortress, which offers from its top a fabulous view over the Val d’Orcia. Here you will stop to sample top-rated regional varietals and learn You will see firsthand where Brunello wine is produced, learn about traditional winemaking techniques and enjoy a guided tour of the cellars. 


Continue on to Pienza, a tiny gem town redesigned by Pope Pius II in the late 15th century, who turned it into his papal summer court. Pienza is famous for its masterpieces like the impressive Cathedral and Palazzo Piccolomini, which used to be the Pope residence but also for the best Pecorino cheese in Tuscany. All around the town shops sell local food and wine absolutely to try!


Lastly, explore Montepulciano a tiny medieval and renaissance hill town where time seems to be passing slowly. For decades, due to its beauty and charm Montepulciano has been chosen as an ideal set for movies. Think of The English Patient and The Devil in Love, and more recently the TV drama The Medici: Masters of Florence just to mention a few.

Montepulciano is best known for its beautiful wines including the Vino Nobile. And here you will enjoy another guided wine tasting tour. Then sit and in complete relaxation enjoy postcard sceneries on the way back to your accomodation.


✔️ Suitable for Families with Kids
• Montalcino
• Pienza
• Montepulciano
Planning, arranging, transportation, driver-guide, and appointments at wineries matched to you.
✔️Private Licensed Professional Local Driver-Guide
✔️Private round trip door to door pickup and drop off at your accommodation in an air-conditioned Mercedes Benz car
✔️Scenic Drive
✔️Brunello di Montalcino Wine Tasting
✔️Wine tasting in Montepulciano
✔️ Free time in Montalcino, Montepulciano and Pienza
• Wine & Food Tastings
•Tips (optional)

How it Works

All of our tours are available upon request, for you and your private party of 2 person minimum. When you are ready to book, tell our Italian-based team when, what you would like to tour, and from where. You will also have the opportunity to tell us if you have a particular winery, you would like to visit. With that in mind, we will create the perfect experience unique to you and yours.


Which wineries will we visit?

We do not have just one set of wineries instead we customize the itinerary based on several factors, some of which include, locations of pick-ups, wine preferences and available wineries for the day (as they require reservations and all have different days of operation and special event scheduling).

Do we stop for lunch ?

Yes. The cost of the meal is NOT included in the tour price. Nevertheless, your private driver-guide would be happy to provide with suggestions to suit your tastes and budgets.

Private Brunello Wine Tour from Florence


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