While Florence and Siena may be the most popular destinations in Tuscany, there is so much more to discover beyond the tourist trail. Within the UNESCO World Heritage area of Val d'Orcia we'll explore medieval villages and hill towns of Pienza (also Unesco), Montepulciano, Montalcino, and San Quirico d'Orcia. So pack your bags and get ready to discover the best places to go in Val D'Orcia Tuscany -it's like a painting come to life, with its golden fields, cypress-lined roads, vineyards and ancient hilltop villages. The natural beauty of this area is truly awe-inspiring, making it a must-visit destination for nature lovers and photographers.
Pienza, often referred to as the "ideal city of the Renaissance," is a true gem of Tuscany. This small town was redesigned by Pope Pius II in the 15th century as 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, including the beautiful cathedral, Palazzo Piccolomini, and the charming streets lined with shops and cafes. Don't miss the opportunity to taste the famous pecorino cheese, one of the best things to do in Pienza and a culinary specialty of the region. With its harmonious architecture, stunning views of the surrounding countryside, and culinary delights, Pienza is a must-visit destination for anyone seeking an authentic Tuscan experience.
Take a stroll along Corso Il Rossellino, the main street that runs through the historic center to discover a range of charming shops. What's great about this area is that it's relatively flat, so unlike some of the other hill towns that have streets on steep hills, it's an easy walk. This is my favorite town to shop in for its wide variety of shops, you'll find everything from jewelry and ceramics to high end food goodies. My favorite shops include:
Tip: If you're looking to buy Pecorino di Pienza cheese, ask the store if they can vacuum seal it for you, as many can, and it makes for easier travel.
Palazzo Piccolomini is a must-visit attraction in Pienza. This magnificent palace, designed by Bernardo Rossellino in the 15th century, is a true architectural treasure. Take a guided tour of the palace (note: the palace can only be visited by guided tour) and explore its beautiful courtyard, adorned with statues and surrounded by elegant arches. Don't miss the "hanging garden," a small botanical garden with laurel trees, box hedges, and flowers, where you can enjoy panoramic views of the Val d'Orcia.
Tip: There is an all inclusive pass (ticket) that includes the entire complex, Palace, Diocesan Museum, Duomo, Crypt and Labyrinth. We found the best part of the complex to be the Palace only and would recommend saving money with the Palace only ticket vs the all inclusive ticket.
No visit to Pienza is complete without tasting the famous Pecorino, a traditional Italian cheese made from sheep's milk and is known for its rich flavor and crumbly texture. In Pienza, you can find a variety of Pecorino cheeses, including those aged with tomato juice for a distinctive red rind and those aged to perfection for a stronger and more flavorful taste. Visit the local shops and taste different varieties of Pecorino cheese, paired with cured meats and a glass of local wine.
Tip: Piccolo Mini Bistrot is a great spot to taste the local cheeses. If you enter from Corso Il Rossellino, walk through the store and head to the back, where you'll find a lover secluded piazza with table service to enjoy a tagliere, a board filled with a sampling of cheeses, meats or both.
For wine lovers, Montepulciano is a paradise waiting to be explored. This hilltop town is renowned for its Vino Nobile di Montepulciano, a rich and full-bodied red wine made from Sangiovese grapes. Take a stroll through the town's historic center and you'll find numerous wine cellars and wineries such Az. Agr. Crociani Susanna Crociani where you can indulge in wine tasting and learn about the centuries-old winemaking traditions of the region. A good one is Don't forget to visit the Church of San Biagio, a stunning example of Renaissance architecture, and enjoy the breathtaking views of the surrounding vineyards. From its wine culture to its architectural beauty, Montepulciano offers a truly authentic Tuscan experience.
There is also some great 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.
Nestled in the heart of Tuscany, Montalcino is a small hilltop town that is famous for its Brunello di Montalcino, one of Italy's most prestigious and sought-after wines. Explore the narrow streets of the medieval town, lined with historic buildings and artisanal shops, and visit the local wine shops for a taste of this exquisite wine.
A visit to Montalcino wouldn't be complete without exploring the Fortezza di Montalcino. This medieval fortress, located in the heart of the town's historic center, 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 and the rolling hills of Tuscany, including the iconic medieval towers that create a unique skyline.
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. Don't miss the opportunity to explore the town's historical sites, including the Horti Leonini, a beautiful Renaissance garden. Admire the architectural beauty of the Collegiate Church of San Quirico, a stunning example of medieval architecture.
Tip: If it's warm out the Horti Leonini offers a great respite from the heat, it's noticeably cooler inside the garden.
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 and reflect on the rich history of this ancient place of worship.
After a day of exploring the hidden gems of Tuscany, it's time to relax and enjoy a traditional Italian aperitivo. Hands down the most incredible spot for an aperitivo in Pienza is Idyllium, located along the outer wall of Pienza. From your seat you can admire the incredible views across the rolling hills.
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 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.
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. Don't miss the opportunity to try other Tuscan specialties such as pici (pasta) wild boar ragu, ribollita (a hearty vegetable soup), and for those looking for less traditional dishes pizzas and hamburgers abound.
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:
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.
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.
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.
When driving in Tuscany, 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. Some ZTLs are electronic signs and note 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.