When it comes to creating an itinerary-my favorite thing to do-I like to budget a few days for exploring and wandering towns/cities, and a few more structured days. It’s no secret that I’m a big fan of Day Trips, because they allow you to maximize your time, generally eliminate having to plan for transportation, and often give you a local’s view of the places you’re excited to see! I’ve always been intrigued by the wine-making process and while I have been to some great wineries in Italy in the past, I’ve neglected to make my way to the Orcia valley, where some of the most well-known wines are produced. I came across a lot of options to experience this area with an Orcia Valley tuscan wine tour, and started doing some research!
On this visit to Tuscany, I wanted to spend a whole day immersed in the Tuscan wine country. On my last couple of visits we made it to a winery here and there, but hadn’t had the opportunity to spend a day among the vineyards. I thought it would be great to see a couple of towns, and maybe some of the more historic producers in the region.
We booked an Orcia Valley Tuscan Wine Tour on Viator for a day in Montalcino, Orcia Valley, Pienza and Montepulciano: Wine and Cheese Tasting Guided Tour from Florence and it was an amazing way to experience Tuscan wines and the famed Pecorino cheese!
We met up with our group and tour guide, Valentina, at the Santa Maria Novella train station. Valetina was so kind, and so friendly (and we were thrilled when she also ended up being our guide a couple of days later when we headed to Tuscany again for more history and wandering)!
We got on the bus, and headed for our first stop, Montalcino! In Montalcino, we tasted the highly regarded Brunello wines at the historic Padelletti Winery! It was so much fun to explore the narrow and winding alleys and pathways in this beautiful city! And yes, we shipped plenty of wine home. 🙂
From Montalcino, we hopped back on the bus and headed to Pienza! In Pienza, we were transported back to the Renaissance in beautiful piazzas and palaces and enjoyed some awesome cheeses, including the famous Pecorino cheese! Here, we also went to a charming little restaurant for an authentic lunch complete with wine, bruschetta, pici Cacio e Pepe (think thick spaghetti tossed in pecorino cheese and pepper-SO GOOD), and almond biscotti for dessert!

We headed back to the bus to head to Montepulciano! In Montepulicano, standing 605 meters above sea level, we enjoyed the highly esteemed Vino Nobile and explored a traditional wine cellar. Fun fact? Montepuliciano wines are my go-tos on most wine lists, especially in the San Diego Little Italy neighborhood! They are robust and enjoyable reds that aren’t too sweet, too dry, or too abrasive! While in Montepulciano, we climbed a LOT of stairs to get to our Talosa, our next winery, but it was worth it to get to the awesome cellar! Once we entered the winery, we headed down several stairs into a cool and inviting cellar full of cool, huge barrels! Then we went into a sparking and inviting tasting room, and tried a couple of wines with a very knowledgable gentleman! As we headed back to the bus, the views at the top of the stairs was incredible! We didn’t get any time to wander on this particular part of the tour, but it was still beautiful to see!
For me, this was a phenomenal experience. Sean and I began learning about wine and tasting wines together when we first started dating in 2012, so it was really special to visit these amazing wine makers together and get a look at the way some of our favorite wines have been produced for centuries! Immersed in culture, charm, and hospitality (and um, lots of wine and cheese), the Orcia Valley tuscan wine tour experience is one we will always look back on fondly!
You can learn more about this trip we took! We did a Florentine Dinner Crawl, explored Bologna for foodies, and spent a day exploring some of the more well-known parts of Tuscany!
Have you ever visited the Orcia Valley? Did you have any favorite wineries or wine experiences in Tuscany? Let me know-I’m always adding to my list!
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