Tuscany is one of the most beautiful regions in the world. La Dolce Vita, the best food & wine, the hospitality of the people, the unique culture and the beautiful landscape make a road trip in Tuscany an unforgettable experience. In this blog post we show you the best travel tips for a road trip in Tuscany.

Best travel destinations in Tuscany


Florence is the capital of Tuscany and a must-see on your road trip in Tuscany. The best way to get there is to park the car outside the city center, as finding a parking lot and getting around by car in the center, can be a real challenge. Park your car in a free parking lot on Viuzzo delle Case Nuove, which is situated in front of a shopping center. From there you can reach the city center easily in a few minutes by tram. Located in the heart of the San Lorenzo neighborhood, you’ll find 19th-century indoor market Mercato di San Lorenzo. There’s a food court on the second level, where you can have your own personal Tuscan tasting of the region’s best local ingredients. If you’re looking for a quick lunch with great food and something for everyone, Mercato Centrale’s upper level is a foodie heaven.
After that, visit the impressive Cathedral of Florence, which is the city’s main sight. From there simply stroll through the streets and let the cityatmosphere work its magic. If you have time, you can visit the beautiful Boboli Gardens.

In the evening, go up to Piazzala Michelangelo, from where you have a wonderful view of the city. Unfortunately, you will share the spot with many other tourists. Therefore, we recommend going a little further up to Abbazia di San Miniato al Monte. Believe us, it’s absolutely worth the hike! You will meet only a few people and have a fantastic view over the city. Lean back and enjoy the sunset.

If you want to have a typical meal in the evening, visit the Ristorante Alla Vecchia Bettola, located just outside the city center, but still within walking distance. The menu is only in Italian, you will be surrounded by locals, it’s loud, fast, chaotic and 100% authentic. Try the pasta of the house and thank us later.

The Chianti area: Radda in Chianti, Greve in Chianti, Volpaia, Montefioralle, Monteriggioni, Certaldo Alto

The Chianti region, which is located south of Florence, is famous for its red wine. If you have time visit one of the many wine tastings in the beautiful vineyards of the province. We also recommend the cooking classes offered here, for example making handmade Italian pasta.
There are numerous small villages in Chianti worth visiting, such as Radda in Chianti, Greve in Chianti, Volpaia, Montefioralle, Monteriggioni and Certaldo Alto. Our secret tip: Castello di Volpaia. A tiny and dreamy village, where time stops, and you can just relax. Not too many tourists find their way here, which is contrary to places like San Gimigiano.

San Gimigiano

The UNESCO World Heritage, San Gimigiano, is recommended in every travel guide. Therefore, many tourists come visit the ancient mountain town. Even though it is very touristic, the medieval city is absolutely worth a visit! Those who successfully complete the parking challenge, will find themselves in a picturesque place, where you can take a walk through the winding streets and feel like in an episode of Game of Thrones.
San Gimigiano


Further south of Tuscany you’ll find the city of Siena, which is typically Tuscan, but very different from Florence. You’ll be impressed by the special architecture and cityscape of this place. Simply stroll around the city and find numerous charming little corners and restaurants.

Pienza & Montepulciano

South of Siena like in Chianti, many small towns are just waiting to be discovered. We went to Pienza and Montepulciano, where we especially recommend the second one. Montepulciano impresses with its balance and serenity, it makes you feel right at home as you stroll along the path that leads through the whole village, past many small local shops and restaurants. There are not too many people, here you can really enjoy your holiday.

Bathing in Bagna Vignoni

The best way to cool off is to go to Bagna Vignoni, but not to the thermal bath found on Google Maps under this name, but to a natural pool that has formed just below the thermal bath and is almost only known to locals. You can find the place hidden in the thicket, just look on Google Maps for Terme Libere. The (short) search pays off!


Those who do not have enough of old Tuscan villages, can visit the hilly city of Arezzo, which is located east of Siena. If you can plan it, you should visit the Giostra del Saracino, the traditional medieval games of Arezzo. This day the city dives in the colors of the four districts, which participate in fascinating duels during the evening. You have the feeling to travel back in time! But beware: Buy tickets on time. There is a similar spectacle in Siena, the Palio di Siena, but the one in Arezzo is a little bit smaller and probably more comfortable.
For dinner in Arezzo you can go to Trattoria Il Saraceno. There you will find one of the best Pici of Tuscany! Speaking of Pici: Pici are hand-rolled, rather doughy, thick noodles, which are typical of this area and just delicious!

Pisa & Lucca

Pisa is one of the most famous cities in Tuscany, but we wouldn’t recommend spending too much time in Pisa. The highlight of the city is the well-known Leaning Tower of Pisa. Simply explore the surrounding area and take walk through the city. Near Pisa you’ll find the charming town Lucca. There you can borrow a bike to discover the city.
Pisa Tower

The best travel time for a holiday in Tuscany

We recommend travelling to Tuscany end of May / beginning of June or from September, as the climate is very pleasant at these times. In the main season, July and August, it can get very hot and the most popular cities in Tuscany are mostly crowded with tourists.

Getting around by car in Tuscany

It is quite convenient that in Tuscany the distances between the different destinations are not far. However, you must keep in mind that you’re not driving on highways but bumpy streets, up and down and at a rather slow speed. Therefore, you should plan enough time to reach the different locations in Tuscany. Furthermore, the parking situation is not quite easy in the most popular destinations in Tuscany, make sure to inform yourselves before driving to the desired destination.

Where to stay in Tuscany region

We wouldn’t recommend staying in the big, touristic places like Florence, Siena or even San Gimigiano. We prefer the so called Agriturismo in Italy, meaning staying at one of the traditional family-owned local farms in the countryside of Tuscany. Better value for money compared to a hotel stay and you can plan day trips from there. Choose a farm with a swimming pool, so that you can cool off after coming home from your tours. Agristurismo is the best way to meet local farmers, learn about italian culture and experience traditional Italian cuisine. And of course..what is better than waking up in a peaceful place, rolling out of bed and enjoying your Italian morning coffee with a view over Tuscany’s magical landscape?
Chianti Region