Tuscany – The Perfect Roadtrip Itinerary

Rolling hills, cypress trees lined pathways, quaint villages, wine, wine and more wine – these are some of the things that come to mind when you think about Tuscany, right?

Tuscany has been my dream destination for years! So, when we first started planning our Italy trip in 2017, we knew that we had to visit this beautiful region of Tuscany.

You will find several tour companies on the web, which provide a day tour from Florence to Tuscany. These tours typically combine a few towns and include lunch and wine tasting. While it is convenient, I recommend visiting this region on your own. It gives you the flexibility to explore the way you want, without having to comply with tour timings and restrictions.

With public transport being somewhat absent in this part of the country, it is advisable to rent a car at least for this leg of your trip. We rented a car through Avis for our entire trip. Most of the towns are pedestrian only and have dedicated parking spots right at the entry.

For a general overview of our two week itinerary please click here

Where to stay

You could set up base in Florence and make day trips to Tuscan towns. However, some of the towns are quite far from Florence and you end up spending too much time traveling back and forth.

Hence, it is advisable to set up base in one of the Tuscan towns. Some of the popular towns are Siena, San Gimignano, Montepulciano, Montichellio, Pienza, San Quirico D’Orcia and Montalcino. 90% of the pictures that you see of Tuscany are of this Val d’orcia region, which is the most beautiful part of Tuscany. Gentle hills, dotted with dark cypresses, and yellow sunflowers make this region postcard perfect.

Now if you really want to get a taste of the countryside, you should stay in an agriturismo. Err, what, exactly, is an agriturismo? Well, it is a “farm-stay.” But it’s also much, much more … and the best way to experience Italy’s countryside! In these agriturismos, breakfast is included. Most of the produce is fresh off the farm, so it is literally a farm to table experience. It also gives you a chance to interact with your hosts and get a glimpse into their daily lives.

For our first trip in 2017, we stayed in a b&b at Montichellio, a tiny medieval hilltop village set in the heart of the Val d’Orcia. It was like an agriturismo and had one of the best views overlooking the valley.

On our second trip here in 2024, we stayed just 2 days in Tuscany. Our primary purpose this time was to break the long drive between Venice and Puglia and revisit some of our favorite towns. We stayed in an Airbnb, around 20 minutes from Montepulciano. It was a quiet neighbourhood with scenic views. While our room didn’t have any view, there was a lovely seating area where we spent our evenings with a glass of wine in hand admiring the views.

How many days required

Most tourists spend 5-7 days in Tuscany (including Florence). While a longer stay is ideal, even a 3-4 day stay gives you enough time to explore the hilltop towns of Tuscany and enjoy the scenic views.

Best Time to Visit

Tuscany is most enjoyable during shoulder season. The months of April end/ May and September are gorgeous. Summers are very busy and very hot.

The first time I visited was in mid-April and let me tell you, Tuscany truly felt like a dream. The rolling hills and greenery was a visual treat. Our second visit to this region was in mid-September. Now, I had seen countless photos on social media where the fields looked green even in September. The Chianti region was still lush green but as we kept driving south, the grass became dry and brown. May be because Tuscany had a very dry summer that year. So, I wouldn’t recommend visiting that late in the year. Go early between April – June when the grass is green and beautiful. The drives will be breathtakingly beautiful!

What to do/ Places to Visit

Wine Tasting

Wine tasting in Tuscany is obligatory – after all, this is the primary reason why you have chosen to visit this region. However, the difficult part will be deciding where and which one! If you have spent even 10 minutes “researching” on the web, you will notice that there are countless options. In addition to wineries, you will find countless shops in towns which offer wine tasting.

After endless research, we decided to do wine tasting in the beautiful Chianti region. It is nestled between Florence and Siena and world famous for its red wine. Driving along this region you get to see vineyard-covered hills with olive groves, each offering a panoramic view of the wine region.

We picked Fattoria Viticcio located near Greve, Chianti for its stunning views. In Tuscany, the Sangiovese grape is king. If you’re drinking in Chianti, it is most likely Sangiovese grape in that bottle. Most wineries in Tuscany conduct wine tours and tastings twice a day – so check with your winery and make reservations in advance.

The tour at Fattoria Viticcio was very informative and lasted approximately 2 hours. We tasted 4 wines – three Chianti Classico wines and one Supertuscan, all of which were excellent.

Sign up for a cooking class

You will find plenty in this area, but I would recommend stopping by Podere il casale. As you enter, you will be greeted with peacocks, followed by the farm’s cats and dogs. You could take a cooking class here and learn how to make pizzas, pasta from scratch. They also offer behind-the-scenes look at the fine art of cheese making. Or you could simply opt for cheese tasting.

Podere il casale offers one of the best views of Pienza, so even if you aren’t doing a cooking class, stop by for picturesque views.

You can simply grab a glass of wine and sit at the terrace overlooking these views. And if you come here for a meal, you will be served dishes created with fresh produce coming from the farmhouse itself.

Chianti Region

Here are the towns worth visiting in Chianti region.

• Greve
• Montefioralle
• Panzano
• Radda
• Castellina in Chianti
• Gaiole

We ended up visiting the first three on our trip.

Greve is considered by many as the doorway into Chianti. It is the largest town in Chianti and the one buzzing with most tourists. Piazza Matteotti is the main landmark in the center of the town. The piazza has a triangular shape and large porticos, which are home to many shops, wine bars and restaurants, which offer typical local cuisine.

If you are looking for sovenirs or ceramics, stop by these shops or simply browse through.

Next on our list was Montefioralle. The village of Montefioralle is nestled in the Chianti hills just above Greve in Chianti. This town truly feels like stepping back in time. It is one of those quaint little towns oozing with charm.Given how small it is and there isn’t much to do, this one is often overlooked by tourists. We had the streets almost all to ourselves and absolutely loved it! As we were strolling by aimlessly, we stumbled upon this restaurant, Il Guerrino. One look at the view and I was SOLD !!

From the terrace, you get a blissful view over a deep valley with vineyards, olive trees, cypresses and wineries. Now, combine that with a glass of the area’s best wines and delicious food. Need I say more?

We had raviolo, bruschetta and wine (duh) and enjoyed a lazy afternoon soaking in the views. Highly recommend this town and this restaurant!

We then stopped by the town of Panzano, located just a few kilometers south of Montefioralle.

It is lovely town to wander through, soaking in the atmosphere and sitting in the main square drinking a glass of Chianti wine. Here you will find several wine bars and restaurants which offer wine tasting. A popular place to visit is the Antica Macelleria Cecchini, a butcher shop famous for its Florentine steak.

If you are looking to grab a meal, check out Il vescovino and Ristorante oltre II Giardino. Both offer spectacular views of the region.

Since we spent most of our morning in Greve and Montefiorelle, we reached Panzano only after 3 pm. By the time we got here, most of the shops had closed and the town was dead. Since there wasn’t much to do or see, we just walked around a bit, grabbed a gelato and left.

Siena

This is one of the biggest and most popular cities in Tuscany.

After you park your car, walk by narrow streets and alleys to the beautiful Piazza del Campo. You can either start your day in Siena right here or instead, head towards the Duomo and return to Piazza del Campo later. The main attractions of the city are located between Piazza del Campo and the Cathedral, so you are likely to spend most of your time here anyway.

Stroll through the streets of the city, browse the shops, wander through the colorful facades, pick up gelatos and get a sense of what daily life is in Siena. As you are walking by the bakeries, try the traditional desserts – Panforte (fruit cake with nuts and spices) and ricciarelli (almond cookies).

Pienza

We went to Pienza with zero expectations, but so glad we visited this town. So much so that it ended up being our favorite Tuscan town! Pienza is the city of cheese. The Pecorino of Pienza is a tasty cheese made from sheep’s milk. The town’s streets are full of small, charming shops selling various types of pecorino, from fresh to aged pecorico. And the best thing is that they let you taste for free – it can go from a delicate flavor to a decisive one based on how aged it is. Stroll by these shops, try Pecorino cheese at the local shops; and you can even buy some for family/ friends.

Once you are done browsing by the shops, take a stroll along its charming streets. Aren’t they simply gorgeous?

And wait you are not done here. Stop for a few photos along the Belvedere lookout point overlooking the valley. The views here are nothing short of spectacular!!

Want to stretch your legs? Stop at Bar Il Casello for a cup of coffee or glass of wine soaking in the beautiful views.

Just minutes away from Pienza is the famous spot where one of the iconic scenes in the movie, Gladiator was shot. Type in “Panaroma il Gladiatore” in GoogleMaps to find this exact spot. You need to park your car on the road and walk about 10-15 minutes on a dirt road to get to this viewing spot. And don’t worry, here you will find a handful of fellow movie enthusiasts snapping away, just like you 😉 

PS- we visited this spot in September 2024. As you can see, the grass has completely dried out compared to the panorama view you see from the Belvedere which was shot in April 2017

Montepulciano

Enter the town through Porta al Prato and begin walking uphill, making your way past the many enotece (wine bars) and shops.  Stop and have a coffee and croissant on your way as you browse the artisan shops selling ceramics, clothes, art, jewelry, trinkets, homemade food.

As you continue walking, you will reach the town’s piazza, Piazza Grande. This is the center of the town, and this is where you will also find the Duomo (cathedral). This building may not look very impressive from outside, but inside you will find some beautiful artworks. You will also find incredible frescoes, tiles, and stained glass.

At this piazza, you will also find Palazzo Comunale, which is a beautiful clock tower. You can climb to the top of this tower for amazing views.

Montepulciano is located atop a hill, so you are guaranteed some amazing views here! Walk past the shops and alleys and you will find some amazing views of the rolling hills. One other beautiful spot is Veduta Panoramica, a viewpoint at the edge of the historic center walls. It is the perfect spot to enjoy the iconic Tuscan views, especially at sunset.As we were exploring the town, we got hungry. We decided to grab lunch at Caffè Poliziano located on one of the winding streets of this town. The best part about this café is the spectacular view of the valley it offers. We ate a hearty bowl of Tuscan soup, roasted rosemary potatoes and ended the meal with a dessert wine. If you aren’t looking to dine here, you can grab a coffee or cornetto or cake and sit at their café admiring the views.

One other specialty of this area is pici, a type of hand-made, thick spaghetti. A classic way to eat it is with a garlicky tomato sauce,

Montepulciano is known worldwide for its Brunello di Montalcino and Vino Nobile de Montepulciano wines, making wine tasting a MUST activity here.

Since we had done a detailed wine tasting tour at Chianti, we were not keen on visiting another winery. Instead, we choose to do wine tasting at one of the wine shops. While we were wandering around the medieval streets of Montepulciano, we stumbled upon a few wine shops which had full blown wine cellars built underneath.

We visited Cantina de’ricci and Fattoria Talosa wineries. Now from the outside, these wineries look like typical wine stores – but once you enter and get down a couple stairs, you will be amazed by how HUGE the cellars are. You will find a maze of stone corridors lined with oak barrels. Once you are done exploring the cellars, you get to taste the wines. In 2017, we paid barely €3 at Cantina de’ricci and the tasting at Fattoria Talosa was absolutely FREE. The rates at Cantina de’ricci have now gone up to €20-€25 depending on the number of wines you taste.

If you have additional time on hand, then check out hot springs of Bagni San Filippo. Tuscany has many hot springs, and this one is quite close to Montepulciano. The hot springs are free and make for a unique experience.

Monticchiello

Since we stayed in this town on our first visit, we spent our mornings and evenings here. Even if you aren’t staying here, it is only a 20-minute drive from Montepulciano and worth adding to your itinerary.

The charm of this town is unlike anything I have ever seen. Montichellio is literally out of a postcard! You will find only a handful of residents here and this town is truly untouched by mass-tourism.

As you are walking by, you will feel like you have stepped back in time. Oh, and not to mention, this town has the best restaurant in all of Tuscany.

This town is quite small, and you only need an hour or even less to see it all. Once you are done, grab a meal at Osteria La Porta.

For a true Tuscan meal, ask any local and 90% of them will recommend Osteria La Porta. This restaurant tends to get busy (for obvious reasons) so be sure to make reservations. In the warmer months, you can sit on the terrace and enjoy your meal staring at the beautiful view. The hostess, Daria, knows her food and wine well, so ask her for a few recommendations and be bowled over by the sumptuous food and wine.

We loved La Porta so much that ate two meals here. Easy decision for us since we were also staying here 🙂

Buonconvento

Driving from Siena to our apt in Montichellio, we stopped by a small town called Buonconvento. It was raining so could not wander around much, but it was such a cutesy town. You can visit the whole town in less than 45 minutes. It is different compared to the other Tuscan towns in the sense that it is not located atop a hill. Since it is a smaller town, it does not feature on every tourist’s list and you will bump into more locals here.

Take Scenic Drives

Val d’orcia region offers postcard perfect views. As you are driving, you will be compelled to stop every few minutes for photos 😊

Most of the scenic views are along San Quirico d’Orcia – Montecchiello – Pienza route. The heart of Val d’Orcia is San Quirico and often the gateway for the scenic Tuscany routes.

Take the SR2 towards south to the first stop Poggio Covili, a farmhouse with a cypress tree lined the road leading to the house. We spotted way too many beautiful cypress tree lined roads on our way so didn’t stop by this specific spot.

From the farmhouse drive towards Monticchiello and make several stops along the Val d’Orcia scenic drive. You will find plenty of beautiful vistas and will be tempted to pull over every few minutes.

On your way back, stop by Cappella di Vitaleta. This small chapel is nestled between the fields and two cypress trees and makes for a scenic view. Park your car and walk around 15 minutes on dirt road to get to this chapel. The best time to visit is during sunrise or sunset when the warm Tuscan light bathes the chapel in a golden glow, creating a truly captivating spectacle. In fact, when we got here, we saw two engagement photos being shot here.

Right next to this chapel, is the beautiful Restaurant Vitaleta offering Tuscan cuisine. Sadly it was closed when we reached in the afternoon.

Another beautiful spot in San Quirici d’Orcia is the Tuscan cypress trees spot. Type in “Cipressi di San Quirico d’Orcia’ on Google Maps and you’ll find a cluster of the towering green beauties along the road.

One of the most photographed place in the entire Val d’Orcia is famous Viale di Cipressi, in the vicinity of Agriturismo Baccoleno. Now, almost every farm or farmhouse in the Val d’Orcia is framed by cypress trees. But the winding row of cypress trees at Agriturismo Baccoleno, surrounded by golden fields, is truly something spectacular.

You leave your car at the side of the road and walk a couple of minutes through the vegetation. The place is enchanting at any time of day, but it becomes especially impressive at sunset time. It was very cloudy the day we visited so didn’t get any vibrant colors. Even though we visited in mid-September when the fields had almost dried out, it still was a visual treat.

 

 

*All prices as of April 2017