72 Hours in Val d’Orcia (as planned by a professional sommelier)

Weekends like the one we spent adventuring around Val d’Orcia, Tuscany make me pinch myself and wonder how I could ever NOT want to live in Italy. I had so much fun exploring smaller towns in Tuscany and it actually made me change my mind about the region. 

If you’ve read my posts about Umbria or Le Marche, you’ll know that I’m a fan of off-the-beaten path adventures through Italy’s central regions. I think both of these regions are underlined from an international perspective and in terms of cost-per-value and the authenticity, they’re both winners in my book.

Despite having visited Florence a few times in the past, it’s never been a town that I fell in love with. On the surface, it can seem touristy, overpriced and overhyped, which is a representation of how Tuscany as a whole seemed to me for quite some time. 

Having a local guide, however, changed my entire perspective. No longer was I frantically using Google and Yelp for restaurant recommendations, but I had my very own restaurant manager and expert sommelier, Francesco Perali, taking me to his favorite spots in the area. 

Giving a little background on Francesco is, I think, necessary, because he’s the one that made my experience in one of Italy’s most luxurious and expensive areas feel local and accessible. Francesco has an extensive background in the Italian food and wine industry and in 2018, was asked to help open up Osticcio, a gourmet enoteca in the heart of Montalcino. Self-described as, “a gastronomic project based on quality, harmony and friendship”, Osticcio is one of those restaurants that you remember your meal at for the rest of your life. Having created a restaurant that is popular with visitors all over the world for its simple but elegant Tuscany cuisine, extensive wine cellar, stellar service and incredible panoramic views, it’s safe to say that Francesco knows what he’s doing when it comes to showing off this incredible area of Italy. 

But more importantly for me (and for the rest of you, now that I’m sharing all of his tips here), he knows what’s up when it comes to showing people around Val d’Orcia. We spent 3 days exploring Orvieto (his hometown), Montalcino, Pienza and many other small towns, stuffing ourselves with more pasta, cheese and wine than I could handle. While Francesco is usually neck-deep in work at this point in the year when tourism in Tuscany reaches a peak, I have Covid to thank for his extra free time. 

Now, all of that said, I hope you enjoy this local’s take on a whirlwind 72-hrs in Val d’Orcia.

Day 1:

2 pm: Arrive in Orvieto 

Take a 1-hour train from Rome to Orvieto (or grab a rental car directly in Florence if you prefer) and take the funicular up to the hilltop city. Tickets are only around €7 but make sure you reserve in advance if you have a particular departure time you’d like to grab.

3 pm: Explore a few sites in the afternoon

Check out my post here for information on exploring Orvieto, but highlights include visiting the 13th-century Duomo, which boasts some incredible frescoes, statues and architecture. I also loved taking a tour of “Orvieto Underground”, where you explore the extensive cave network dating back 2,500 years that inhabitants originally used for food storage and even pigeon-breeding and was eventually used as shelter during WWII. 

6:30 pm: Aperitivo time

Have aperitivo at FE3.Ø, a microbrewery in the heart of historic Orvieto with amazing local craft beers and tapas-style snacks. I’m not a huge fan of beer, but their summer ale paired with popcorn and peanuts (YES) was so refreshing. 

8 pm: Dinner

Decide between pasta and pizza at Charlie, but whatever you decide, make sure you ask for a table outside in their romantic courtyard and crack open your first bottle of Rosso di Montepulciano.

11 pm: Departure from Orvieto

Drive to Montalcino and promptly pass out after a day full of traveling, eating and drinking.

Day 2:

Wake up bright and early so you can hit all of the things on your to-do list

9 am: Stroll around Montalcino

Wander around Montalcino and gaze longingly at Osticcio (closed until Spring 2021). It’s a small town so you’ll be able to cover a fair amount a ground this morning. Note that most of the shops and restaurants here are very wine focused but in the morning, the view over Val d’Orcia is stunning.

11 am: Visit the Abbey of Sant’Antimo

First up, a visit to the Abbey of Sant'Antimo, a former Benedictine monastery. While I didn’t think this was as impressive as San Galgano, which is open to the sky without a roof, it was still a fun stop. The monks also produce many local Tuscany products so if you’re in the market for some olive oil, jam or toiletries, there’s a small shop outside you can stock up at. 

1 pm: Lunch

Have a quick lunch break outside of the abbey (I recommend a panino with prosciutto and Tuscan pecorino) and head off to your private wine tasting. 

2 pm: Wine tasting and tour at Argiano

I’m calling this part of this Montalcino guide a mini-post because I NEED to give you all the deets on the one wine-tasting we did over the weekend. P.s. I get wordy about things I’m really excited about (i.e. historic villas cum wineries) so consider yourselves warned. 

Getting a private guided tour of the villa grounds, vineyard and wine production area at Argiano felt like one of those once-in-a-lifetime experiences that you never forget. I had no idea what we were in store for until we showed up with Francesco but by the time our 2 hours with guide-sommelier, Laura, had passed, I wanted to move in. 

The 14th-century Villa Bell’Aria is stunning and its surrounding farmhouse guest accommodations, gardens, pool and chapel are similarly breathtaking. The entire winery and villa has been undergoing renovations for the past 5 years and was finally completed this year. But the part of Argiano that I found the most impactful was the wine cellar. 

With an atmosphere that felt like a cross between a luxury designer shop and medieval dungeon, the entire area was stunning. There were hundreds of valuable bottles of wine stored and put on display and don’t even get me started on that spiral staircase. 

Of course, the actual wine tasting was also fantastic. We tried 6 of the winery’s reds, including a phenomenal Brunello di Montalcino (of course) and while I did not make the leap in purchasing a €200 bottle, it was a close call. 

I think the best part of an experience like this is that it’s easily adaptable for people at all levels of wine-knowledge. Edoardo and I learned so much about the estates history and the different cultivation and production methods used (they are plastic-free and use organic methods of pest control!) but even wine-expert Francesco found it interesting as well. 

After a quick break back at home, it’s time for more town-hopping, eating and drinking!

6 pm: Passeggiata time

Take a walk in Bagno Vignoni and check out the thermal pool in the center of the town. Take a thousand pictures, as one does. Consider eating there, but decide you want a more local feel so now you’re headed outside of the city to an agriturismo.

8 pm: Dinner

Have the Tuscan meal of your dreams at Dopolavoro La Foce. This 0-km restaurant is on the grounds of a larger villa with guest houses and they are doing Tuscan food right. Their food strikes the perfect balance between fresh flavors and rich traditional cooking. I got the pici al ragu to split as an antipasto (as one does) and followed it with a delicious tagliata. Their self-produced red wine was also incredible.

11 pm: dopocena

If you can still walk comfortably after your indulgent dinner, check out the charming town of San Quirico d'Orcia and grab a glass of wine at one of the many enotecas that have outdoor seating.

Head back home and collapse into a wine/food coma

Day 3:

Decide you need a slight detox from all the eating and drinking so you take the morning slow and enjoy coffee on your balcony with a view of the valley. 

10 am: Under the Tuscan Sun photoshoot

Your first stop is the Cappella della Madonna di Vitaleta, better known as: that small church with a great view that everyone takes photos next to. It’s become an informal symbol of this part of Tuscany and getting there means you’re walking through some gorgeous fields and enjoying a view over the rolling hills of the Val d’Orcia. No complaints here. 

11 am: Visit Pienza and explore one of the region’s most picturesque borghi

If you can’t get enough of small-town Tuscan charm, Pienza is a must-see. While less famous than other surrounding cities like Siena, it has a very curated feel with the most amazing gardens and flowering front stoops I’ve seen in Italy. The view of the surrounding countryside from the city walls is breathtaking, perfect for the amateur photographers out there like myself. 

1 pm: Lunch:

While we stopped for yet another plate of pasta at Case Nuove, I think a better option is to grab a sandwich from one of the many salumerie (meat and cheese shops) that line the main road in Pienza and take it to eat overlooking the view. 

2 pm: Arrivederci

At this point, we made our way back to Orvieto to catch an afternoon train back to Rome, but if you’re staying in the area longer or have a car, you might have a more flexible schedule and have time to check out the Terme di Saturnia or a few other other small towns.