What Should I See In Tuscany? Perfect Tuscany Road Trip Itinerary

Road trip around Tuscany was always on my bucket list. I’m in love with Italian food and its landscape. This summer my partner and I decided to spend a week in Tuscany. We went there in late August and the weather was perfect, maybe almost too hot. We started planning the whole trip one week before we headed out because we weren’t sure if we were going to be able to travel because of the Corona restrictions. We knew which places we wanted to visit and booked Airbnb’s in advance and asked some of our friends who’ve already been there to give us some tips about the best restaurants and bars. We had the most amazing time in Italy and we will definitely return there. If Tuscany road trip is also on your travel list then you’re probably wondering what are some best places to stay, what you should see in Tuscany and how many days do you need to explore everything. Don’t worry, you will find all the answers in this itinerary.

1. Verona

We decided that we’re going to drive with our car to Tuscany and our first stop was Verona. From Heidenheim (Germany) to Verona there is approximately 6 hours drive if there is no traffic. We didn’t want to spend the whole time on the highway so we took a more scenic route through Austria and Italy.

We arrived there in the afternoon and first drove to our apartment. We booked one night with Ai Ponti Verona and we loved it. The room was nicely decorated and very clean. I would totally recommend it. It is also very close to the city center. Piazza delle Erbe, Juliet’s Balcony and other must-see places are only 10 minutes away.

The rest of the day we spent wandering the streets of Verona. We walked by the famous Arena, kissed under Juliet's Balcony and climbed the stairs of Torre dei Lamberti, one of the only remaining towers in Verona. In between, we took a short break for dinner and really good ice cream from Gelateria Impero. Yummy!

We spent almost 24 hours in Verona and we saw basically everything so if you would like to stop there like we did, I’d say 1 day is more than enough to get a good feel for the city. Also, the center of the town is walkable so you won’t need to take any public transport. We really enjoyed our stay in this city of love and gorgeous architecture.

So, here is the list of the things you should absolutely see in Verona:

  • Piazza delle Erbe

  • Verona Arena

  • Castelvecchio

  • Juliet’s Balcony

  • Torre dei Lamberti

  • Castel St. Pietro

  • Piazza dei Signori

2. Florence

The next stop on our way to Tuscany was Florence. We were really excited about this city because we heard only good things about it. We stayed there for 2 nights in a beautiful Cantoria hotel close to the city center. The hotel has the most amazing rooftop where you can sit, relax, and enjoy the view of the cityscape from the terrace. During our stay in Florence we ate delicious sandwiches from Antico Vinaio (there is usually quite a long line in front of the restaurant but it’s worth the wait!), had really good wine and appetizers in Le volpi e l’uva and tried the best ice cream from Gelateria Perche No.

Florence is literally packed with amazing architecture and places of significance like the Cathedral/Duomo, Ponte Vecchio and Uffizi Palace. You will definitely need more than just a day to visit everything and really take in all this cultural city has to offer. I would recommend staying in Florence for at least 2 days.

Places you should definitely see in Florence:

  • The Cathedral/ Duomo

  • Ponte Vecchio

  • Uffizi Palace

  • Palazzo Pitti

  • Boboli Gardens

  • Piazzale Michelangelo

  • Church of Santa Maria Novella

  • Piazza del Duomo

3. Montepulciano

From Florence we drove to Montepulciano again avoiding some of the main roads which took us about one hour and a half. Montepulciano is a small town on a hill in the Italian province of Siena. It’s best known for the wine called Vino Nobile and beautiful views over Tuscan landscape. Montepulciano is a beautiful small city full of ancient churches and elegant Renaissance palaces. The best way to explore it is by walking through it and enjoying the stunning views of the surrounding countryside called Val d’Orcia. Since the beginning of our road trip, we wanted to do a proper wine tasting and Montepulciano was a perfect place to do it. We chose Cantina De Ricci. Their wine cellar is one of the oldest there since the Ricci family was born in 1150. We booked the tour of the cellar and wine tasting. We were not disappointed. The tour was really interesting and their wine is simply amazing. If you’re into wine tasting too, I would recommend you visit them. During the wine tasting, we met a lovely couple from Germany who told us about the cheese shop nearby, where you can buy different sorts of cheeses, bread, wine and meat products. They will put everything into one cute picnic basket and you can have a lunch break right there at their terrace with a beautiful view of Val d’Orcia and the city of Montepulciano.

We were so excited and drove there immediately. Caseificio Cugusi is only 10 minutes away from the Montepulciano and it’s definitely worth a visit.

4. Siena

We spent only a few hours in Montepulciano since it’s a small town and in the afternoon we drove to Siena, which is the capital of the Siena province. We booked a room for one night in La Coroncina Aparthotel. They only have a couple of apartments and they are lovely decorated and cozy. The owners are really nice and hospitable. Breakfast was probably our favorite part because they served it to us in a picnic basket and we sat outside on the terrace and enjoyed a quiet morning.

The historic center of Siena was declared by UNESCO as a World Heritage Site. Siena is known for its medieval cityscape, art, and lively atmosphere. The most interesting place for us was the Piazza del Campo which is the main square of the city and has a really interesting shape as it is built on a slight hill slope. You will also find a lot of bars and restaurants there. Every attraction in Siena is within 5 minute of walking distance, so you won’t need more than 1 day to explore the whole city.

Places you should visit in Siena:

  • Piazza del Campo

  • Cathedral of Santa Maria Assunta

  • Torre del Mangia

  • Porta Pispini

  • Fortezza Medicea

5. San Gimignano

The next stop on our Tuscany road trip was San Gimignano and it was definitely one of our favorite places in Tuscany. This charming small town is located about 50km southwest of Florence and if you’re planning a Tuscany trip you should add it to your list. San Gimignano is known for 13 tower houses that remained from the original 70. They give the town a distinctive skyline. The most famous place in San Gimignano is without a doubt the medieval center with Piazza della Cisterna which has the triangular main square. There you will find street musicians, bars, restaurants and Gelateria Dondoli, once awarded best ice cream in the world and the best ice cream place in Tuscany many years in a row.

Near the city center there is a history museum called San Gimignano 1300. They have a large scale model of the city as it appeared in 1300. They recreated the scenes of medieval street life and the model really shows details of the city’s architecture. San Gimignano is usually packed with tourists and finding a good parking spot is very difficult that’s why I would recommend you to park somewhere a bit more outside of the city.

6. Lucca

After we finished wandering the streets of San Gimignano in the afternoon, we drove to Lucca which is located one hour and a half away on the western coast of Italy. Lucca’s historic old town is surrounded by beautiful medieval city walls and is also called a city of hundred churches because of the large amount of historical religious structures. We decided to stay 2 nights there since Pisa and Cinque Terre (last 2 stops on our road trip) are pretty close and we could easily drive back to Lucca in the evening. The old town of Lucca is small so you can see all the places in a couple of hours. We were most impressed by gorgeous architecture and public squares. We first stopped by at Piazza dell'Anfiteatro, where we had delicious pizza and good wine. Then we walked to San Michele in Foro, a stunning church in the centre of Lucca. From there we continued to explore the town and stopped in a couple of cute little stores in between.

Things to see in Lucca:

  • Piazza dell’Anfiteatro

  • San Michele in Foro