3 Days in Tuscany: Exploring Val d’Orcia With a Day Trip to Cortona

How We Spent 3 Days in Tuscany

Day 1: Explore Val d’Orcia

Here’s how we spent 3 days in Tuscany, with a focus on Val d’Orcia and a few unforgettable stops along the way.

Visit Pienza

Since we were staying just outside Pienza, it made sense to start there. This hilltop town is small but packed with charm, Renaissance architecture, and sweeping countryside views. You can’t go wrong staying in or near town.

Pienza is part of the Val d’Orcia region, recognized as a UNESCO World Heritage Site for its preserved Renaissance town planning and iconic landscapes. It’s worth setting aside time to wander.

• Palazzo Piccolomini: Built for Pope Pius II’s family, it’s worth stepping inside for the panoramic garden views over the Val d’Orcia.
• Duomo di Pienza: The Renaissance cathedral anchors the main square. Look closely at the exterior walls for damage from World War II, still visible today.
• Church of San Francesco: Small, peaceful, and tucked off the main street, this simple church dates back to the 13th century.

Stop into the local shops as you go—especially the cheese shops. The smell of pecorino di Pienza practically calls you in. If you plan to sample it for lunch, hold off until our suggested spot just outside town (more on that below).

Just outside historic Pienza, Bindi Enzo is a salumeria worth making time for. They offer a beautiful variety of pecorino cheeses from their family farm, local salumi, and—what ended up being our favorite—some of the best porchetta we had in Italy.

We stopped here for lunch, and it turned into one of the highlights of our time in Tuscany. Hungry and ready to try everything, we probably over-ordered. Enzo’s son behind the counter prepared a generous spread of pecorino and salumi for two, plus a porchetta sandwich that I still think about.

We sat down with our feast, shared a bottle of sparkling water and a glass of Montepulciano wine, and soaked it all in.

There’s seating inside the shop and a few tables outside on nice days. You can also browse their shelves, stocked with local goodies and wines—it’s easy to leave with more than just lunch.

Tip: If you want the porchetta, get there early. We watched as the crusty slab was slowly carved away—and gone by the time we finished eating.

Tour Idea:
Bike trip from Pienza to Montalcino through the Val d’Oricia [book here]

Visit Cappella della Madonna di Vitaleta

One of the most scenic spots in Val d’Orcia is Chiesa di Vitaleta, a small chapel nestled in a peaceful valley, surrounded by cypress trees and golden hills. It’s one of the most photographed locations in Tuscany—and for good reason. Seeing it in person was just as dreamy as the photos.

You won’t be able to drive right up to the church, so be prepared for a short walk. When you enter the chapel into Google Maps, it’ll lead you to a gated back road. You’ll see other cars parked along the shoulder—this is where you’ll leave your car and continue on foot.

The walk takes about 5–10 minutes, depending on how often you stop to take photos. You’ll get a view of the back of the church as you approach, and the setting is beautiful at any time—but arriving around sunset adds a little magic.

Wear comfortable shoes, especially if you plan to wander the area.

• 🕙 Hours: Open Tuesday–Sunday, 10:30 AM to sunset.
• 🍷 There’s a restaurant nearby that looked ideal for an aperitivo, but it was temporarily closed during our visit.

Visit Bagno Vignoni

We ended Day 1 with a visit to Bagno Vignoni, a small village in Val d’Orcia known for its ancient thermal springs—used since Roman times.

The main square is centered around a large pool filled with steaming spring water. While you can’t bathe in it, it’s still a beautiful sight, especially in the evening light. If you visit earlier in the day, you can explore Parco dei Mulini, a path that leads behind the square and along the cliffs where you’ll find remnants of old mills and thermal waterfalls.

Bagno Vignoni is also home to several spas and wellness retreats if you’re looking to plan a relaxing day in the region.

For dinner, we had reservations at Osteria del Leone, located right in the heart of the village. It’s one of the top restaurants in Bagno Vignoni, and we booked it through The Fork app the same day. It ended up being one of our favorite meals in Tuscany.

The restaurant sits in a historic stone building with rustic charm. Exposed wood beams and multiple small dining rooms give it an intimate, cozy feel.

We ordered the handmade pici pasta, a Tuscan classic, served al dente with a rich beef ragù. Since truffle was in season, we also had the tagliolini with shaved white truffle—no regrets.

For dessert, we shared the Bavarese al pistacchio, a pistachio Bavarian cream topped with raspberry sauce and pistachio crumble. Hands down, one of the best desserts we had in Tuscany.

Day 2: Scenic Drive Through Val d’Orcia and Crete Senesi

On Day 2, we set out to explore more of Val d’Orcia, with a scenic drive through the Crete Senesi loop, a stop in Monticchiello, and a sunset visit to Montepulciano.

There’s so much to take in that even with a full day, we couldn’t see everything. You could easily stretch this into two or three days if you love road trips, slow travel, or photography. But with limited time, we focused on just a few key stops—and it was still a beautiful experience.

Drive the Crete Senesi Loop

One of the most scenic drives in Tuscany, the Crete Senesi winds through the backroads of the Siena region, known for its lunar-like landscapes, wheat fields, and rows of cypress trees. If you drive the loop without stopping, it takes about 1.5 to 2 hours, but there are plenty of reasons to pull over and soak in the views.

We started from Pienza, heading north and looping through the countryside before reconnecting back toward Val d’Orcia.

This route is also popular with cyclists and hikers. You’ll pass vineyards, small villages, and scenic viewpoints that beg to be photographed. We stuck with the drive due to time, but if you have a full day, you could easily turn it into a relaxed mix of driving, short walks, and maybe a winery stop.

Visit Montechiello

After our scenic drive through the Crete Senesi, we headed south from Buonconvento to Monticchiello, a tiny village that feels like it stepped out of a fairytale. We parked just outside the town and walked in.

This peaceful hilltop village is full of charm—stone houses, narrow cobblestone alleyways, and sunbathing cats that act like they own the place. We wandered slowly, taking it all in and stopping by the Church of Santi Leonardo e Cristoforo, a small but beautiful parish church.

The views of the Tuscan countryside from here are stunning, and the quiet atmosphere makes it a nice contrast to the more visited towns.

Foodie Pick: If you’re here around lunchtime—or even for a sunset dinner—Osteria La Porta is known for its views and excellent food. Be sure to make a reservation in advance.

Visit Montepulciano

For our final stop of the day, we drove north to Montepulciano, where we had dinner reservations.

This medieval hill town is known for Vino Nobile di Montepulciano and Chianina beef, and it’s full of scenic streets and Renaissance architecture. As you drive up, keep an eye out for the stunning Sanctuary of the Madonna di San Biagio, a 16th-century church just outside the city that immediately stands out against the landscape.

Once inside, wander your way to Piazza Grande, the main square, lined with historic buildings and beautiful views. Along the way, you’ll pass wine shops, artisan stores, and cobblestone alleys that make it easy to linger.

Montepulciano is not only worth visiting—it’s also a great option as a home base if you’re planning three days in Tuscany, especially if wine tasting is high on your list. Just remember, you’re going to be in a hilltop town.

Tour Ideas:
Wine Tour E-bike Experience [book here]
Winery Tour & Tasting Experience [book here]

For dinner, we had reservations at Osteria Acquacheta, one of Montepulciano’s most popular spots—and for good reason. This rustic Tuscan osteria is known for its Bistecca alla Fiorentina, and we booked weeks in advance to try it.

This was one of the more unique dining experiences we had in Italy. The osteria is small, busy, and very much run on a tight schedule—with charm. There are only two dinner seatings: 7:30 PM and 9:30 PM, and everyone is seated at once. You may end up sharing a table with another party, like we did. (We had a great time chatting with a lovely young couple.)

Reservations can only be made by phone, and yes, they’re necessary.

The process is part of the experience. First, drink orders. Then the owner personally comes around to talk bistecca: how big a cut your table should get, whether you want the filet portion (which is extra), and how it’s prepared.

After the discussion, he disappears into the back to butcher the steak and brings it to your table to inspect before cooking. The final product? A massive, rare steak served with zero pretense—and a lot of flavor.

Important note: They only serve Bistecca one way, which is rare. Asking for it cooked further is highly discouraged (and likely won’t go over well).

We kept things simple: a small pasta to share, a couple of sides, and then the star of the show. The bistecca arrived sizzling and perfectly cooked. The portion was huge but just enough for the two of us. We were full, happy, and glad we had saved our appetite.

Day 3: Day Trip to Cortona

For our final day, we took a break from Val d’Orcia and planned a day trip to Cortona, located in the province of Arezzo. The drive from Pienza to Cortona took about 1 hour and 35 minutes, and it was worth every minute.

We’ve wanted to visit Cortona ever since watching Under the Tuscan Sun—and it didn’t disappoint. While we spent most of the day wandering the city center, we instantly fell in love with the town.

Cortona is a hilltop town perched on the southeastern slope of Mount Sant’Egidio, overlooking the Val di Chiana valley. The views here are incredible. The higher you climb, the more rewarding they get.

Start in Piazza della Repubblica, the town’s main square, and let yourself get lost in the maze of narrow cobblestone streets and colorful buildings.

We loved our day in Cortona and can definitely see ourselves returning. If you’re planning a visit, we put together a full post on how we spent one day in Cortona, Italy, including where we ate, what we loved, and a few things you shouldn’t miss.

Tour Ideas:
Cortona Private Walking Tour [book here]
Easy E-Bike Tour of the Cortona Valley [book here]

Other Ways to Spend 3 Days in Tuscany

There’s no single right way to spend 3 days in Tuscany—it really depends on what you want to see most. The region is large, and driving distances between towns can be longer than they look on the map. When planning your Tuscany itinerary, it helps to pick one area to focus on.

Here are a few other ideas for how to spend three days in Tuscany:

• Base yourself in Siena and explore nearby towns like San Gimignano, Monteriggioni, and Volterra.
• Stay in Florence and take day trips by train to see the Leaning Tower of Pisa, visit Lucca, or join a tour through Chianti wine country.
• Do what we did and stay in Val d’Orcia, using a car to explore towns like Pienza, Montalcino, San Quirico d’Orcia, and the surrounding countryside. We also added a day trip to Cortona, which was the perfect way to end our trip.

Each of these Tuscany itineraries offers something different—whether it’s wine tasting, Renaissance cities, or peaceful hill towns. Just choose what speaks to you most and build your trip from there.

How to Get Around Tuscany

Once you’ve decided how to spend your 3 days in Tuscany, the next step is figuring out how you’ll get around. Your best option depends on where you’re staying and what you plan to see.

For our 3-day Tuscany itinerary, we rented a car to explore Val d’Orcia at our own pace. After our road trip, we returned the car and continued our travels.

Where to Stay in Pienza and Val d’Orcia

There are plenty of great places to stay in Val d’Orcia—from small B&Bs to agriturismos and countryside villas. Your best choice depends on what kind of experience you’re after.

That said, a car is essential—especially if you’re staying in the countryside, like we did. Many of the most peaceful and scenic stays in Val d’Orcia are located just outside the main villages.

You’ll want to consider:

• Do you prefer walkability and access to restaurants? → Stay in town.
• Do you want a more rural experience with wide-open views and quiet surroundings? → Look just outside the villages.

If you’re driving, you’ll have the flexibility to stay outside the towns and explore at your own pace. For this trip, we chose to stay just outside Pienza, and it was exactly what we wanted—quiet, scenic, and central to everywhere we planned to visit.

BEFORE YOU TRAVEL TO ITALY, CHECK OUT THESE RELATED READS:

• Extend Your Trip With 2 Days in Florence
• Florence, Italy: Day Trips You Can Take
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• We Keep Returning to Italy? Here’s Why
• Italy Quotes: Your Next Foodie Destination