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Road trip in Italy: Tuscany in velvet

Live your best dolce vita in one of the most beautiful regions of Italy with this road trip in Tuscany in vespa.

Small picturesque villages and hills with a loss of view on which vine feet are located... Benvenuto in Toscana !

Located in the north west of the country in the form of a booth, the region gathers nearly 290 communes on an area of 23,000 km2. Beyond its ideally located geography, between land and sea, and its mild Mediterranean climate, Tuscany enjoys a historical reputation.

Indeed, it is the cradle of Italian mythical authors like Dante, and unmissable artists like Michel Ange and Botticelli (to name only three). Its gastronomy also contributes to strengthening the identity of the region.

The capital of Tuscany, Florence , made it radiate the region internationally. It is therefore a city to be discovered absolutely to learn more about the Tuscan culture and the regional heritage.

So we have concocted a road trip from Florence to discover Tuscany in another way: in vespa. In Italian, the vespas are iconic colored scooters that now integrate into the Italian fashion. The advantage is that you can discover the region at the expense, imagined in a Fellini movie... Then put the gas, and andiamo !

From Florence...

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Photo credit: Shutterstock – Pfeiffer

  • 📷 To be visited: Santa Maria del Fiore Cathedral, Ponte Vecchio, Palazzo Vecchio, Piazza della Signoria, Boboli Garden, Palatine Gallery, Office Gallery and Palazzo Pitti
  • Where to stay: in this beautiful Airbnb with terrace and views of Florence

Explore "La Bella" to start your road trip in Tuscany in velvet will immediately put you in the mood! The Tuscan capital, surrounded by hills, combines the dynamism of a student city with the solemn aspect of its architectural heritage. Indeed, Firenze is one of the most visited cities in Italy thanks to its historical and artistic heritage.

First of all, discover all the monuments that make the charm of the city like the Cathedral of Santa Maria del Fiore: a Gothic-style religious building whose construction lasted more than 100 years! The dome is also the name of the city. A few meters from the cathedral, you can stroll through the Campanile de Giotto. If you are in good physical shape, climb the 416 steps to have a magnificent panoramic view of Florence.

You will also have the opportunity to visit other must-sees in the city as a crossing Ponte Vecchio , above the Arno. There you will find jewelers who continue to live the tradition of the city. Indeed, in the Renaissance, the city had managed to extract gold, contributing to its wealth. Also, do not pass next to the Palazzo Vecchio a high place of local politics in the Middle Ages.

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Photo credit: Shutterstock – Dennis van de Water

Beyond these sights, let yourself be carried by the magic of the city and stroll around the alleys of Florence, and explore its places, such as Piazza della Signoria. You can also lose yourself in the sumptuous Boboli garden .

And to return to the trace of the famous Medici family, take a tour at the Palatine Gallery, the Office Gallery and the Palazzo Pitti . On the detour of a place, don’t hesitate to stop for local cheeses accompanied by Chianti from the Tuscan vineyards. You will need energy in the middle of all these visits!

Then go get your bladder back to a rental agency. The two-wheeled Tuscan adventure begins...

From Florence to Siena: on the Chianti road

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Photo credit: Shutterstock – Rasto SK

  • 🗺 in Itinerary: Florence to Siena
  • 📍 Traject: 90 km • 3 hours in vespa
  • 📷 To be visited: Greve di Chianti – Panzano – Lamole – Radda – Crete Senesi
  • Where to stay: in theAirbnb Villa Bonelli

This journey during your road trip to Tuscany in the countryside will make you cross beautiful Tuscan villages! It is in this region that you will find the vineyards that produce the local wine, the Chianti.

First, make a first stop at Greve di Chianti and Panzano: two small villages worth a look. You can walk in the alleys, access beautiful viewers for "a premium countryside view", and walk in the gardens. You will feel the smell of olive trees and cypresses mixed with that of the clean linen that the inhabitants extend to their windows.

Reinforce your preferred vehicle and continue your path the roads of Chianti through Lamole and Radda! There, you will see vineyards lost sight and can stop on the road to take some photos. Attention, however: the roads between the vineyards are sometimes filled with gravel. Don’t go too fast!

Do not hesitate to taste good wine in one of these villages and simply discover the peaceful life of the cities of Chianti. And if you push into the countryside doesn’t scare you, then continue to the Crete Senesi where you will enjoy what the Tuscan countryside has more beautiful to offer you.

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Photo credit: Shutterstock – H-AB Photography

Finally, it is time to make a stopover in the city Siena , known for its Cathedral, as well as its historic centre.

More intimate than Florence, Siena is full of wonders such as the famous Piazza del Campo which welcomes the famous horse races (the Palio), as well as the Santa Maria della Scala Museum. This former hospital, among the oldest in Europe, is now an unmistakable cultural centre.

Finally, walk on the streets of the city or on foot: it is the best way to find secret buildings and make pretty pictures. You may fall on a Fortress Medici or on the Basilica di San Domenico.

From Siena to Grosseto: explore rural Tuscany

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Photo credit: Shutterstock – Marco Rubino

  • 🗺 in Itinerary: from Siena to Grosseto
  • 📍 Traject: 227 km • approximately 4h45 in vespa
  • 📷 To be visited: San Gimignanello – Asciano – Montalcino – Pienza – Montepulciano – Sorano – Cala Grande
  • Where to stay: in this beautiful Airbnb close to Grosseto with sea view

After your stage in Siena, it is time to take the road through the Tuscan countryside to reach the coast, towards the city of Grosseto.

Of course, depending on your time and budget, you can skip steps or stay longer in some villages. Because in velvet, this part could be particularly long.

However, we recommend that you discover the village of San Gimignanello and eat a delicious pizza in one of the small restaurants in the area. For dessert and coffee, wait to arrive in Asciano, and sit on the terrace of a shaded square. There you can ride in the middle of the hills surrounded by cypresses! More fun than the urban scooter, isn’t it?

Continue your road trip in Tuscan with a discovery of the villages of Montalcino, Pienza and Montepulciano, "beads of renaissance" where you can admire ancient traditional stone buildings. The villages are well maintained and preserved, making every visit pleasant.

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Photo credit: Shutterstock – Alexander Ingerman

Your journey continues in the region of Grosseto with a stop at the fabulous village of Sorano. In this city, you will have the strange impression of going back to time... Indeed, this picturesque village is at the top of a rocky ridge, making it even more impressive. Overlooking the village, you will find the fortress of Orsini, built in the 14th century.

It is time to regain urban dynamism by exploring Grosseto. This town of 83,000 inhabitants has the advantage of being close to the coast. Discover its Piazza Dante where you can eat. This is the most important tourist point in the city. You should also go out of the beaten paths and explore the coast. You will find the Parco Naturale della Maremma nearby, as well as the Cala Grande, ideal for stinging a head in case of high heat!

From Grosseto to Pisa: roll on the coast

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Photo credit: Shutterstock – StevanZZ

  • 🗺 in Itinerary: from Grosseto to Pisa
  • 📍 Traject: 178 km • approximately 3h30 in vespa
  • 📷 To be visited: Cala Civette – Baratti – Pisa
  • Where to stay: in this Airbnb chic and historical

Did you like to roll hair in the Tuscan countryside? Then you may be as conquered by the coastal routes that will allow you to reach Grosseto to Pisa .

To start this long-lasting part of the road trip in Tuscany, we recommend driving a few kilometers outside Grosseto and stopping at Cala Civette. There you can enjoy beautiful beaches and other discreet coves. Access to Cala Civette is not the simplest ones, and you will have to leave your faithful companion (vespa) on the parking lot. But believe us, it is worth stopping in this corner of paradise and stinging a head in the turquoise sea. A real plus: the beach is very clean and preserved.

Find your velvet that will have quietly taken advantage of a parking space sheltered under an olive grove to drive to Baratti. This commune, which belongs to the city of Piombino, makes you enter the province of Livorno .

You can discover the famous Gulf of Baratti: a sumptuous place to swim and enjoy a sunset (if you decide to stay a night). In addition, the beach is surrounded by immenses pines that reinforce its Mediterranean postcard look. In addition, enjoy being in the area to enjoy fresh fish and seafood!

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Photo credit: Shutterstock – f11photo

Once satisfied by this coastal stage, it is time to reach the city of Pisa. Of course, you can't miss the famous leaning tower. Completed in 1372, the tower of Pisa is the campanile of Notre-Dame de l’Assomption. It is one of the must-see monuments of the piazza dei Miracoli (place of the Miracles) listed in UNESCO World Heritage.

Do not hesitate to climb at the top of the tower for a breathtaking view of the Baptistery and the camposanto. Did you know that the turn of Pisa began to look at only a few years after its construction?

Enjoy being in Pisa to discover other museums, stroll around the ramparts, and eat in the local establishments. Moreover, the city houses one of the best pizzerias in the region: Quarto d’Ora Italiano.

Pisa and return to Florence

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Photo credit: Shutterstock – canadastock

  • 🗺 in Itinerary: from Pisa to Florence
  • 📍 Traject: 147 km • approximately 3h in vespa
  • 📷 To be visited: San Gimignano – Cole di Val d’Elsa
  • Where to stay: in this Airbnb beautiful in the centre of Florence

Ready for the final stage, we propose you to go out of the beaten paths to discover the pearl of Tuscany: San Gimignano.

This city, among the most picturesque in the region, is a must-see during a road trip to Tuscany in the countryside. Moreover, it is also part of UNESCO’s World Heritage in Europe. It is also a very ancient city, which has preserved its heritage almost intact. You can admire the famous towers, alleys, common square and ramparts.

After a day's visit, enjoy it to stroll through the olive trees... And if you want to restore: direction Peruca! Remember to book in advance, especially in high season.

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Photo credit: Shutterstock – ermess

On the way back to Florence, we recommend a second stop at the Colle di Val d’Elsa. The discovery of this village will marvellously close this road trip in Italy in vespa! Walk in the medieval town, and discover small hidden palaces and other surprising buildings. You can also visit the Duomo of the Cathedral of Santi Marziale and Alberto, as well as its crypt.

After two or three hours in the village, you will be ready to take back the handlebars of your bladder full of memories. Drive a hundred kilometers to Florence to make your velvet and take the time to tell us your experience!

Scarlett Green

Scarlett Green

I'm Scarlett Green, a passionate traveler forever captivated by the world's allure. My life is a tapestry of vibrant experiences, from summiting majestic peaks to embracing cultural diversity. Every destination tells a story, and I'm here to share those stories with you. Through my words, I aspire to ignite your wanderlust, offering insights, tips, and the sheer thrill of discovery. Let's embark on this extraordinary journey together, unraveling the world's hidden treasures and creating lasting memories along the way.

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