Every time someone asks me what my favorite place in Italy is, “Tuscany” is out of my mouth before they even finish asking the question. This region of central Italy is famous for its beautiful landscapes, rich history, and of course – wine. Tuscany is one of the largest regions of Italy, stretching over nearly 9,000 miles of land. The rolling hills of the Val d’Orcia, charming little towns, and incredible food and wine make it one of the best destinations in all of Europe. We spent one week on our Tuscan road trip – here’s our guide to the Tuscan countryside!
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Our Itinerary
Day 1 + 2: Florence
We started our Tuscan road trip in the capital of Tuscany, Florence! This city is absolutely buzzing with incredible art, history, and food! Read my guide to the best things to do in Florence for all the details on what to do while you’re there.
Here’s the highlights:
SEE THE DUOMO | The most important thing to see in Florence! An icon of the Renaissance period.
MAKE YOUR OWN PASTA | Our cooking class in Florence was one of the highlights of our time there! Here’s the class we took.
THE PITTI PALACE AND BOBOLI GARDENS | A beautiful palace with five museums and gorgeous gardens showcasing many Renaissance sculptures.
WATCH THE SUNSET OVER THE ARNO | Head to the Ponte Vecchio bridge for beautiful sunset views over the river!
PIAZZA DELLA SIGNORIA | Home to the Palazzo Vecchio, as well as an open-air museum full of Renaissance sculptures.
SEE THE DAVID | Visit one of Michelangelo’s most prized works at the Accademia Gallery!
Day 3: Siena + Chianti
On your third day, get up early and venture south into the Tuscan countryside. Pick up a rental car in Florence (we booked ours through SIXT at the Santa Maria Novella train station) and head south onto the SR222. Also known as the Chiantigiana, this is one of the most scenic drives in Tuscany! Drive slowly so you can enjoy the views, and be ready to make stops along the way to snap photos or just take it all in.
CHIANTI
Driving along the SR222, you’ll arrive in Chianti first. This region is known for their sprawling vineyards and incredible wine! Stop at a winery for a tasting and try the incredible Chianti Classico that the region is famous for (this type of wine can only be made here)!
NOTE | Many wineries only offer tours and tasting on weekdays, although some will offer them on the weekends by special request.
Siena
Next, get back in the car and continue down the SR222 until you reach the vibrant town of Siena. Siena is a bit larger than some of the other towns we will visit on this road trip, but still feels so dainty after spending the last few days in Florence. The town is so full of history and has quite a lot to see and do. Grab some lunch, then go enjoy the town! Here’s some things to see and do:
THE CATHEDRAL | Siena’s cathedral is beautifully unique, with white and black striped marble decorating both the exterior and interior. The entire complex includes Cathedral, the Piccolomini Library, the Gate of Heaven, the Baptistry, the Crypt, the Museo dell’Opera, the Panorama from the Unfinished Façade, and the Oratory of St. Bernardino. You can purchase your pass here.
PIAZZA DEL CAMPO | This square is where the Palio horse race is held! The horse race is held twice a year and is quick, only lasting about a minute and a half. The riders and horses represent their contrada (neighborhood). Each contrada is represented by a different color and mascot. As you walk through Siena, you’ll see flags hanging from the buildings showcasing the colors and mascot of whichever contrada you’re in. It’s such an interesting bit of culture here in Siena!
EXPLORE THE HEART OF SIENA | Get lost in the maze of streets winding out from Piazza del Campo. Stop for an espresso in one of the cafés, or pop into one of the leather stores for some quality shopping.
BASILICA OF SAN DOMENICO | This church is located high on the hills of Siena. The church is beautiful, and if you head just down the street you’ll see incredible sweeping views over Siena!
TRAVEL TIP | Most restaurants and some shops in Siena observe siesta from about 3pm-7pm, so make sure you make it here on time for lunch before everything closes down!
I would recommend spending the night here in Siena. We didn’t do this and instead drove another hour to our accommodation in Montepulciano. While this was fine, I do feel it made us feel a bit rushed in Siena and we were absolutely exhausted by the time we got in bed.
Here’s some accommodations in Siena to check out:
VILLA DEL SOLE | An adorable little bed and breakfast in the heart of Siena with great views over the town.
IL BATTISTERO SIENA RESIDENZA D’EPOCA | A boutique hotel in a great location overlooking the Cathedral.
Day 4: Pienza + Val d'Orcia
Its day four of our week in Tuscany! Today, we will head even further south into the Val d’Orcia, the region famous for its rolling hills and sweeping views. Take the SR2 south, then the SR146 towards Pienza. The SR146 is another famous route in Tuscany known for its incredible views, so make sure you’ve got enough time in your itinerary to drive slowly and make stops along the way! It’s a little over an hour drive, but took us close to two hours with all the stops.
Pienza
The town of Pienza is probably the smallest on this entire list. The main street through the town only takes about five minutes to walk from one end to the other! In my opinion, Pienza is the most charming town in all of Tuscany. Every street was so magical, and it felt so romantic and quaint!
WALK ALONG CORSO IL ROSSELLINO | This is the main street that runs through the historic center of the town and is a great way to start exploring the town.
GET LOST | I think I have probably put this on every travel guide I’ve ever written, but it will always be one of my favorite things to do. As you walk along the main street, adventure down the little pathways winding off from it. This is how you will truly experience the magic of Pienza – quiet little streets decorated with florals and greenery, personal art galleries displayed on the steps, people hanging their laundry to dry in the breeze. It’s just magical!
PIAZZA PIO II | This little plaza is located along the main street, and is home to Pienza’s cathedral and Palazzo Piccolomini.
WALK THE CITY WALLS | Walk along the Via del Casello and enjoy sweeping views over the Val d’Orcia. You will find several viewpoints along this walk, as well as a few bars. Stop at Bar Il Casello for a meat and cheese board and a glass of wine! Make sure you try the pecorino di pienza cheese – it’s famous to this area!
Crete Senesi Vista
Crete Senesi Vista is a long, winding road lined with cypress trees and a backdrop of the rolling hills of the Val d’Orcia. Visitors rolled out blankets and picnics as they watched the sun set over the hills and cast a golden glow against the trees. This was one of the most stunning landscapes I have ever witnessed, and I simply cannot recommend it enough!
Crete Senesi Vista is about a 30 minute drive north of Pienza, essentially halfway in between Siena and Pienza. I know it seems counter-intuitive to drive 30 minutes back up north after spending the morning driving south, but trust me: you’ll want to see this at sunset. If you don’t want to backtrack, you can absolutely stop here on your way down to Pienza and skip the 146, but seeing it at sunset was magical. Either way, don’t miss this!
Your GPS will direct you to the main cypress path, which actually belongs to a hotel. Because of this, you cannot drive down the path or park on it. Continue on the main road and you will see plenty of spots to park along the street!
Get Checked in to your hotel
After the sun sets, head to your hotel and get some rest. I recommend staying in the Montepulciano region as its a great base for the rest of your time in Tuscany!
Day 5: Relax in a Tuscan Villa
After all of the driving and exploring over the last four days, it’s time to slow down and take a break. Tuscany is full of gorgeous borgos, villas, and hotels, all offering a beautiful sanctuary of relaxation.
We stayed at Borgo San Vincenzo, a stunning borgo just outside of Montepulciano. Originally a Tuscan outpost, renovations in 2022 created the gorgeous 21-room boutique hotel that stands here today. The hotel is complete with a full-service pool deck, fire terrace, restaurant, and cocktail bar. Winemakers dinners, aperitivo classes, and bike rentals are all offered. You can book a variety of excursions and tours as well, if you are inclined.
Our fifth day in Tuscany was well-spent. We began with a slow breakfast of Tuscan breakfast sandwiches and cappuccinos before heading to the pool deck. We spent the majority of our day lounging by the pool, reading a book with a spritz in hand. We enjoyed lunch by the pool, then later had an incredible charcuterie board with wine pairings to match! The service here is absolutely impeccable, and the owners are such wonderful people. I cannot recommend a stay here enough! It was the perfect place to unwind after all the excitement of the last few days.
Day 6: Cortona
Situated high on the hills of Tuscany, Cortona is often considered to be one of the most beautiful Tuscan towns for its incredible views. It was recommended to me by a friend who has family there, so of course I had to visit! It’s about a 40 minute drive east from Montepulciano, near the border of Umbria. The town is so charming and authentic, you won’t see nearly as many tourists here as in other towns!
PIAZZA DELLA REPUBLICA | The main square of Cortona, highlighted by Palazzo Communale. You will find quite a few wine shops, restaurants, and gelaterias here. There was also live entertainment when I visited!
PIAZZA GARIBALDI | From here, you can see one of the best views of Cortona and the countryside!
WALK ALONG VIA NAZIONALE | This is the main street through the town, connecting Piazza della Republic and Piazza Garibaldi. You will find plenty of restaurants, wine shops, art galleries, and more along this street! I loved how authentic the shops in Cortona were – you found more artists and handmade goods rather than touristy souvenirs.
GET LOST | I bet you already knew this was coming.. There are tons of little side streets branching off Via Nazionale. Some still have medieval buildings still in place from the 14th century!
PIAZZA DEL DUOMO | Another fantastic viewpoint over Tuscany! The cathedral is also located here.
HAVE A MEAL AT OSTERIA DEL TEATRO | This was one of the best meals I had during my time in Tuscany! (With the exception of our hand-made pasta, of course.) The goat cheese pasta was to die for! This is one of the more popular restaurants in Cortona, so I would recommend making a reservation.
Day 7: Montepulciano
For the last day in Tuscany, we opted to stay close to our hotel and explore the fairytale town of Montepulciano. Stroll through the streets, admire the views from the hilltops, and enjoy plenty of Tuscan wine on your last day here in Tuscany!
VISIT A WINERY | Montepulciano is known for their fantastic wine. I recommend Canneto, a small winery just outside of the main town with breathtaking views. Their wine tasting includes four wines (although we got to try five!) and all were incredible. The entire winemaking process occurs on site too – harvesting, aging, etc. Make sure you try the Vino Nobile – a wine made from grapes that can only be grown in this region.
WANDER THE STREETS | Walk along Il Corso, the main path winding through the town. From here, you can explore the side streets and find amazing leather shops, wine shops, restaurants, and gorgeous views.
PIAZZA GRANDE | The main square in Montepulciano, home to the Cathedral, Town Hall, and a few palaces.
TEMPLE OF SAN BIAGIO | A Renaissance temple built in the 16th century. If you visit Canneto for a wine tasting, you’ll actually pass this on the way!
VADUTA PANORAMICA | A beautiful viewpoint over the rolling hills of the countryside.
This concludes our week long Tuscan itinerary! From here, we headed down to Rome, but you can venture wherever you’d like. The world is wide, happy traveling!