Discovering Authentic Tuscany, Cheers To The Towns of Val D’Orcia

While Florence and Siena may be the most popular destinations in Tuscany, there is so much more to discover within the UNESCO World Heritage area of Val d’Orcia. This region offers more than breathtaking landscapes of golden fields and cypress-lined roads, with incredible big red wines, olive oils.

Come along with Spritzience as we explore the medieval villages and hill towns of Montepulciano, Montalcino, and San Quirico d’Orcia. We’ll find the best restaurants, spots for wine tastings and shops.

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1. Montepulciano: The Wine Lover’s Paradise

For wine lovers, Montepulciano is a paradise waiting to be explored on the edge of the Val D’Orcia region of Tuscany. This hilltop town is renowned for its Vino Nobile di Montepulciano. It’s a rich and full-bodied red wine made from Sangiovese grapes. Primarily crafted from the Sangiovese grape, locally it’s referred to as Prugnolo Gentile. This wine is celebrated for its rich flavors and balanced structure. It holds a prestigious position among Tuscany’s esteemed red wines, alongside Brunello di Montalcino and Chianti Classico.

Contucci Cantine near the main square, is a great spot to wine taste. With cellars built into the the 11th- 13th century town walls. It’s the only remaining operational historic cellar in town. They offer a range of different guided tours, visiting the cellar and rooms of Palazzo Contucci, built in the 1500s.

What I liked best about this tasting, was the range of foodie goodies on offer. As you can have a plate of local cured meats, two types of local pecorino cheese and bread with their Extra Virgin Olive Oil. Or try a smaller variety of snacks depending upon the specific tour you select. As I’m not a big red wine drinker, I left with a few bottles of the incredible tasting olive oil.

As you stroll through the town’s historic center , make another stop at one of the wine cellars so you get a feel for the range of wines on offer. Az. Agr. Crociani Susanna Crociani is a good one, where you can indulge in wine tasting and learn about the centuries-old winemaking traditions of the region.

Shopping in Montepulciano

Within the Val D’Orcia towns, Montepulciano has some of the best shopping with small boutiques selling souvenirs and clothes lining the main street. My favorite treasures from Montepulciano are linens with olive and cypress trees on them – I bought a couple of oversize tea towels that I use as table clothes on my garden tables.

The selection and prices I saw at Biagianti Since 1913 were amongst the best of the linen shops I’ve seen in the region, and these are artisan made. Plus they have an online shop, so if you find when you get home that you missed some pieces (a tablecloth, placemats, curtains) or are just looking to replenish your linens you can place an order.

2. Montalcino: Brunello Wines from the Val D’Orcia Region

Montalcino is a small hilltop town in the Val D’Orcia region of Tuscany, famous for its Brunello di Montalcino. It’s a prestigious Italian red wine produced exclusively in the vineyards surrounding the medieval town of Montalcino in Tuscany. Crafted from 100% Sangiovese grapes, locally known as “Brunello,” this wine is celebrated for its bold fruit flavors, and notable acidity, which contribute to its exceptional aging potential.

Upon tasting, one can expect rich notes of blackberry, black cherry, chocolate, leather, and violets. It pairs well with grilled meats and other game. This is also a popular wine in the U.S, with Americian buying 1 out of every 3 bottles. So it’s a good idea to peruse the wine shops of this Val D’Orcia town. You’ll find bottles of something special you’ve tasted, that you may not easily find in the U.S.

Wine Tasting in Montalcino

So where should you taste the famous Brunello di Montalcino? The Corte Pavone Winery provides gourmet wine and food pairings, allowing guests to savor Brunello in a refined setting. Take a tour of the estate. Then order some of what you like best, as they ship throughout Europe and to the U.S.

Another good spot to enjoy this wine, is in the atmospheric Alle Logge, in the main piazza (town square). Known for its extensive wine list, including over 200 local wines many from the Val D’Orcia region, it’s an ideal spot for lunch or an aperitivo. They have a cute indoor area with wooden tables, antique fireplace and views looking out over the Val D’Orcia countryside.

However, outside sitting areas draw Spritzience in. This spot delivers with a wood beamed loggia- from the Renaissance period. As it overlooks the main square, Piazza del Popolo, the people-watching is topnotch.

Explore the Fortezza di Montalcino

A visit to Montalcino wouldn’t be complete without exploring the Fortezza di Montalcino. This medieval fortress, is located in the heart of the town’s historic center. It offers panoramic views of the surrounding countryside and a glimpse into the town’s rich history. From the top of the fortress, you can enjoy breathtaking views of Montalcino. You’ll also see and the rolling hills of the Val D’Orcia, including the iconic medieval towers that create a unique skyline.

3. San Quirico d’Orcia: A Medieval Masterpiece in the Val D’Orcia

Step back in time and immerse yourself in the medieval beauty of San Quirico d’Orcia. This small town is a true masterpiece of medieval architecture, with its well-preserved city walls and historic buildings. Take a leisurely stroll through the town’s cobblestone streets. Explore its charming squares, and admire the intricate details of its medieval architecture.

As you explore the town’s historical sites, head into the Horti Leonini, a beautiful Renaissance garden. If it’s warm out the Horti Leonini offers a great respite from the heat, it’s noticeably cooler inside the garden. Then head to the Collegiate Church of San Quirico, a stunning example of medieval architecture.

Admire the Collegiate Church of San Quirico

No visit to San Quirico d’Orcia is complete without admiring the beauty of the Collegiate Church of San Quirico. This stunning example of medieval architecture is located in the town’s historic center, just off the side of the Via Francigena.

Step inside the church and marvel at its intricate details, from the ornate sculptures to the beautiful frescoes adorning the walls. Take a moment to soak in the peaceful atmosphere. Reflect on the rich history of this ancient place of worship.

Aperitivo Time-Best Place for a Spritz

If you happen to be in Montepulciano at aperitivo time, head to Caffe Poliziano, where there are small tables on the terrace with incredible views of the Val D’Orcia countryside.

In San Quirico d’Orcia, the Garden Bar on the terrace of the hortus garden has super comfy chairs, where you can enjoy a cocktail in the shade of their olive trees. To access the bar, enter via the Palazzo del Capitano Hotel.

Authentic Tuscan Cuisine

One of the highlights of visiting Tuscany is indulging in its authentic cuisine. From the rich flavors of traditional Tuscan dishes to the exquisite wines produced in the region, there is something to satisfy every palate. You’ll want to try other Tuscan specialties such as pici (pasta) wild boar ragu, or ribollita (a hearty vegetable soup). If you’re looking for a less traditional dish, pizzas and hamburgers are also on offer.

• Alle Logge Di Pienza: Located in Montalcino, is a great wine bar, serving authentic dishes and an amazing outside seating where you can soak in the atmosphere of the town.
• Caffe Poliziano: A historic ristorante serving up food since 1868 in Montepulciano. Ask to be seated on the bottom floor for incredible views (if you’re dining). This is a great spot to try the pici pasta.
• Ristorante Fonte Alla Vena: One of the top rated restaurants in San Quirico D’Orcia, known for amazing ingredients, and modern plating this is a wonderful spot to enjoy exceptionally delicious Tuscan cuisine. I’m a huge fan of artichokes and the special they had with liquorizia was by far the best I’ve ever had. I thought about canceling my entree order to have more artichokes – I now dream about this dish.

Best Boutique Hotels in Tuscany

These are some of my favorite boutique hotels, they have great locations in the old town so you’re walking distance to local activities, and no driving needed is to get home from wine bars or restaurants in the evening:

• Bandita Townhouse: Located in Pienza, this stylish hotel offers modern comforts in a historic setting.
• Palazzo del Capitano: Situated in San Quirico D’Orcia, this luxurious hotel combines elegance with top-notch amenities and service, including a spa, an outdoor garden and pool.

Day Trips in Val D’Orcia and Tuscany

While you’re in Tuscany, take the opportunity to explore a few additional unique towns to enjoy amazing food and architecture.

Pienza: A UNESCO Renaissance City

Pienza a UNESCO “ideal city of the Renaissance” has become a must-visit destination for connoisseurs of cypress tree selfies, authentic Tuscan food and pecorino cheese.  A short drive takes you to Pienza, also in the Val D’Orcia region of Tuscany. Where you can spend a day, soaking in the unique feeling of this Tuscan hill town, with a population of just over a thousand people. Pienza got a facelift, by Pope Pius II in the 15th century. He redesigned the town to make it a model Renaissance city.

As you stroll through Pienza‘s historic centre, a UNESCO-listed Heritage Site, you’ll be captivated by its architectural treasures. One of which is the beautiful cathedral, another is the Palazzo Piccolomini.Come along with Spritzience as we craft your perfect weekend itinerary, highlighting the best restaurants in Pienza Italy.

Siena Secrets: 17 Things To Do In Siena Italy

If you’re planning your dream Italy trip, let me offer a tip straight from a New Yorker who’s called Milan home for 10 years: Siena Italy is one of the most soul-stirring cities in the country—and easily one of the most rewarding spots on any Tuscany travel itinerary. Whether you’re into medieval history, Gothic cathedrals, quiet gardens, or vintage cars roaring through Renaissance piazzas, there are so many unforgettable things to do in Siena Italy that you’ll want to linger longer than a day.

Unforgettable Authentic Dining: Day Tripping to Pistoia Italy

Enter the idea of taking a trip to Pistoia Italy… just a short 45 minute train ride from Florence. With its ancient walls and a car-free historical city center, it’s a great city to explore rich Tuscan culinary heritage. You’ll see monumental palaces, ancient churches and a couple swoon worthy piazzas. Just perfect for sitting and lingering over a glass of wine and a great meal as you people watch daily Italian life.

Getting Around the Val D’Orcia

Traveling from Florence

If you’re traveling from Florence, the most convenient way to get to the towns in the Val D’Orcia is via car. There are many car rental agencies a short distance from Florence’s central Santa Maria Novella train station. From Florence it is approximately a 1 hour and 45 minute drive, depending upon the traffic to Pienza, Montepulciano, Montalcino, or San Quirico d’Orcia. Tuscany’s well-maintained roads make it easy to navigate and discover hidden gems along the way.

Traveling from Rome

If you’re traveling from Rome, coming via is car preferable as public transit requires a combination of buses & trains. Driving from Rome, it’s approximately 2 hours and 45 minutes, depending upon traffic to arrive to the towns of the Val D’Orcia.

What are the best roads to see cypress trees?

One of the most iconic sights of Tuscany is the rows of cypress trees that line the country roads. One of the best roads to see the cypress trees is the Strada del Vino Nobile, which takes you through the heart of the Val d’Orcia. As you drive along this scenic route, you’ll be treated to breathtaking views of the countryside, iconic cypress trees and wineries.

Driving tips and avoiding ZTL

When driving in the Val D’Orcia, it’s important to familiarize yourself with the rules of the road. Be aware of speed limits, which can vary depending on the road you’re on. It’s also essential to know that many historic city centers have restricted zones called ZTL (Zona a Traffico Limitato) where only authorized vehicles are allowed.

Some ZTLs are well marked and others more difficult to see, so when in doubt -to avoid any fines, be sure to park your car outside of these city centers and walk into town. A common ZTL sign configuration is white sign with the wording “Zona Traffico Limitato” and a red circle below it.

You’ll find a mix of electronic and regular signs, sometimes also noting if the ZTL is enforced as it may change during certain hours. They tend to have cameras to snap photos of license plates of those entering the ZTL, so that fines can be administered to those who don’t have approved access to the ZTL.

Val D’Orcia Resources

Hotels

• La Bandita Townhouse, Corso Il Rossellino 111, Pienza https://la-bandita.com/townhouse/the-property/
• Palazzo del Capitano, Via Poliziano 18, San Quirico d’Orcia https://www.palazzodelcapitano.com/en/hotel-borgo-in-tuscany/

Restaurants

• Alle Logge di Piazza, Via Giacomo Matteotti 1, Montalcino, +39 0577 846 186
• Caffe Poliziano, Via Voltaia nel Corso 27/29, Montepulciano, +39 0578 758 615
• Ristorante Fonte Alla Vena, Via Dante Alighieri 137, San Quirico d’Orcia, +39 0577 897 034

Shops

• Azienda Agricola Crociani Susanna Crociani, Via del Poliziano 15, Montepulciano +39 0578 757 919
• Biagianti dal 1913, Piazza Michelozzo 5, Montepulciano, +39 0578 757 261

Wineries

• Contucci Cantine, Via Del Teatro 1, Montepulciano +39 0578 757 006
• Corte Pavone Winery, Localita Corte Pavone, Montalcino, +39 335 1898 353