Tuscany, one of my most favorite places on Earth! Fields of sunflowers and vineyards for miles make a Tuscan road trip the perfect place to drive aimlessly. How long should you go for? We decided we needed enough time to experience all Tuscany has to offer. That’s why an 8 day Tuscan road trip seemed like the perfect amount of time to see everything.
Getting around Tuscany can be challenging since public transportation is limited. That’s why a road trip is a perfect idea. We decided to rent a car. I think this is the easiest way to get around Tuscany. You’ll want to rent a car in a city that isn’t too big and difficult to navigate. For example, I’d stay away from renting a car in Rome. Driving out of a big city can be ultra complicated and stressful. A Tuscan road trip is supposed to be the ultimate relaxation vacation!
For the first timer, creating a map and itinerary of where to go can be difficult. This was the route that we took. We started in Florence and then hit:
- Greve in Chianti
- Siena
- Pienza
- Montalcino
- Montepulciano
- Monticchiello
- Volterra
Day 1- Greve in Chianti
We drove from Florence and found our hotel in Greve in Chianti (20 mins South of Florence). We stayed at Hotel Vicchiomaggio. It was a charming, old castle in the Tuscan hills. They even make their own wine! It was delicious. Highly recommended the Chianti Riserva. The grounds are stunning and made for perfect morning walks. Breakfast was included and so yummy! Most hotels in Italy will include a continental breakfast buffet. We spent 2 nights here and used it as a home base. We were tired so we just lounged by their infinity pool before our wine pairing dinner. This place is perfect for just relaxing in the Tuscan countryside!
Day 2- Chianti exploration
Explore nearby wineries. We went to the Antinori Winery. If you don’t make it to any other winery you HAVE to go to this one. It was something out of a James Bond movie. The architecture was incredible. Rows of vines even covered the roof of the cellars. We didn’t have a reservation for their restaurant but got so lucky they had space for us. Make sure you reserve this in advance!
Day 3 & 4- Siena
One of my favorite cities! We stayed in upper part of the town. You don’t want to make the mistake of staying outside of the town since Siena sits atop a hill. All towns in Tuscany are mostly cobblestone streets. Don’t waste time bringing heels, and be ready for the wheels on your luggage to get really torn up. We spent our time walking around and had the best pizza at Il Pomodorino. The cathedral is a must see. We also had aperitivo in the duomo (central square) where the famous horse races take place.
Day 5- Pienza
A tiny town in the heart of the Val d’Orcia. We stayed in a small bed and breakfast in the town (Pienza is another hilltop city). We used this as our home base for two days. We chose this town over Montepulciano because we had been to Montepulciano before and wanted to experience something different. I’m so glad we did because this town has very little tourist attractions. For me I like to feel like a local. Pienza is a hidden gem not many tourists know about. We spent the day driving here and exploring the little town and shops. The whole town is walkable in half a day. While on our walk we found the perfect spot on the edge of town to enjoy happy hour and they made the most beautiful meat and cheese board! If you don’t order the classic orange Aperol Spritz while in Italy you’re missing out. This region of Italy is known for truffles so I naturally ordered the truffle pasta at dinner one night. Yum!
Day 6- Val d’Orcia drive, Montepulciano + Montalcino
Waking up in Pienza we found our car and drove around the Val d’Orcia. If you’ve ever seen a really beautiful painting of Tuscany this was probably it. The name means valley of the river. There’s a famous drive through this valley that takes you to Montepulciano, Montalcino (home of Brunello wine), and tiny Monticchiello. Monticchiello is the tiniest town I’ve ever been to. You could seriously walk around it in 15 minutes. We met the sweetest man who owned a linen shop and bought some handmade dish towels and aprons after a quick walk around the town. If you don’t have time to visit all of those towns I’d at least go to Montepulciano and drive the loop of the Val d’Orcia road. My number one rule is stop for gelato once a day…. so definitely abide to this rule too!
Day 7- Volterra
This was my new favorite town! Apparently this is where portions of Twilight was filmed. Volterra and San Gimignano are right next to each other We’ve been to San Gimignano before and absolutely loved it. This time we wanted to try something new and didn’t have time to go to both. Volterra is a little more sleepy and less touristy than San Gimignano. Once again we chose to stay in the city center since the majority of the city is on top of a hill. We walked around, enjoyed some wine and visited the Roman Amphitheater ruins. On the way out we found the yummiest little panini shop named Panineria Al Vicolino. You have to try it if you’re there! I got the panini with prosciutto, mozzarella, arugula drizzled with truffle honey. It would be perfect to take on a picnic or if you’re continuing on with your Tuscany road trip.
If you find yourself with more time on your Tuscany road trip there’s definitely more cities to visit! Other places we’ve been to and loved are Lucca, and Orvieto (although technically not Tuscany but very close). Most people want to visit Pisa to see the leaning tower, but the town itself was extremely touristy and not so charming.