The ultimate 5 day Tuscany road trip with the Vespa

Italy is probably one of our favorite countries for road tripping. We already did a road trip in Puglia and one in South Tyrol. Tuscany has been on our bucket list for quite some time. But we definitely wanted to make it something special. That is how we ended up at The Vespa Trip, which offers organized road trips with Vespas in various destinations. And yes, also in Tuscany! When we saw this, we didn’t hesitate for a second. And a few weeks later we already left for Italy for a 5 day Tuscany road trip with the Vespa.

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Why a Tuscany road trip?

Tuscany in Italy is a region that appeals to the imagination. The landscape with rolling hills, winding roads, extensive vineyards, golden grain and sunflower fields, driveways with impressive cypress trees, picturesque, medieval villages and historic towns with numerous sights, attract many visitors every year.

To really experience Tuscany as it should be, you can’t help but immerse yourself in this mix of nature and culture. That is why it’s advisable to explore different places within this region during your vacation. The best way to do this is of course through a road trip.

But maybe you were already aware that Tuscany is also the birthplace of the iconic Vespa. So why not opt for a road trip with a Vespa? Just a little more original, more adventurous and more authentic than by car.

Why we chose for the The Vespa Trip?

Dreaming of a Tuscany road trip with the Vespa, a lot of questions quickly came to our mind. What do we do with our luggage? Which places are we going to visit? What distances are feasible with the Vespa? And how do we find those beautiful routes that allow us to enjoy this beautiful landscape? Such a trip requires a lot of research and planning.

Although I really like to plan our trips myself, I postponed this trip many times because I always got stuck somewhere in the organization. Because of this, this adventure remained on our bucket list for years until I discovered The Vespa Trip a while ago.

The Vespa Trip is a concept of Travelbase, that offers multi-day tours with Vespa in various destinations, including Tuscany. This one is called ‘Il Giro Classico’ and takes you along the beautiful Tuscan landscape to the most impressive, historic cities in this region. The best of both worlds. When I looked at the itinerary in detail, I was immediately hooked.

Besides the intinerary, the entire organization is arranged for you. All I had to do was provide my correct details and book the flights. So The Vespa Trip was actually the perfect answer to all my questions that I got so stuck on.

During The Vespa Trip you can choose to follow the guide in a group. But you can make the trip perfectly on your own via the pre-programmed routes in the GPS. You can of course also switch from day to day! Because we like to spontaneously stop along the road when we see a nice spot, we decided to make the trip ourselves with the GPS and this worked out perfectly.

The communication in the group takes place via a WhatsApp group. All important information is shared on a daily basis on this platform, such as when we can bring our luggage to the van, when the group is leaving, where we can park during stops, … This information is also important if you decide to drive individually. But also great tips are shared in this group, such as the best restaurants in a place that’s on the program that day. I personally found this to be a very useful tool.

How to travel to Tuscany?

Traveling to Tuscany is possible in different ways. For a short trip I would recommend traveling by plane. From Belgium you can fly to Pisa with various airlines from Brussels Airport or Brussels Charleroi Airport. From the airport you can take the Pisa mover or taxi to the city center. If you buy a ticket for the Pisa mover (5 euros per person) for two people, it is about the same as the price of a taxi. So on the way back from our hotel to Pisa airport we opted for a taxi. We paid 12 euros for this ride.

If you have plans to continue road tripping through Italy before or after The Vespa Trip, you can also travel to Pisa by car.

Are you traveling from another destination in Italy? Then Pisa is very easily accessible by train or bus. We arrived in Verona and then took the train to Pisa. It only took us 2 hours. In the past we also took the train from Pisa to Florence and Cinque Terre. We can say that public transport in Italy is very well organized.

When is the best time to travel Tuscany?

Tuscany generally has a mild climate. The weather depends a bit on which place you visit. For example, it will be slightly warmer on the coast, in the cities and in the valleys than in the mountains.

The period with the best chance of sun starts from April to October. During the summer months of July and August it can get very hot. Of course, the breeze on the Vespa is a welcome refreshment.

If you are free outside the summer months, I would definitely recommend this to visit Tuscany. We went there in June and the temperature was ideal for a Tuscany road trip with the Vespa.

Our 5 day Tuscany road trip with the Vespa.

Arrival in Pisa

A few days before our departure I received a notification that I had been invited to the WhatsApp group of The Vespa Trip. With great enthusiasm I pushed the button to accept the invitation. It got real! You know, that feeling of ‘yes, we’re almost leaving’! Through this WhatsApp group we were informed how the arrival in Pisa would go, such as when the travel guides would receive us and where we still had to arrange a few things for our Vespa.

However, the day of departure was not without a struggle. Our flight had been booked for weeks. We were supposed to take off at 2.30 pm and arrive in Pisa at 4 pm. But due to the strike at the airport, our flight was cancelled. We were not informed of this until 11pm the day before. For a moment I saw this whole trip fall apart. There was even a small tear involved. But where there’s a will, there’s a way. I had to find a solution. After browsing the net, I found another affordable flight to Verona from another airport. But it left at 6 in the morning, so we had to pack everything together and leave almost immediately. It was a night without sleep.

At 8 am we arrived at Verona airport. We went by bus to the train station where we took the train to Pisa. We were on the road for about 2 hours and had to switch once in Florence. So we arrived in Pisa around 1 pm. Fortunately our hotel, Hotel La Pace, was near the station and our room was already available. So we could take a quick nap before meeting our travel guides.

In the afternoon Hans and Célia, our travel guides, were welcoming all the participants of The Vespa Trip in the lobby of the hotel. There we received a brief explanation of how the trip would go. We also received our GPS because we chose to drive the trip individually and not follow the guide.

Then we went into the center of Pisa to the Vespa rental near the leaning Tower of Pisa. We had to stop by to try on a helmet and to scan our driver’s license. We couldn’t pick up our Vespa until the next morning. And since we were in the neighborhood we also paid a quick visit to the famous Leaning Tower of Pisa.

On the way back we enjoyed a delicious typical Tuscan sandwich in an authentic setting at L’ostellino Pisa. In the meantime, the were made arrangements in the WhatsApp group to have a drink with the group that evening at Argini e Margini along the banks of the Arno. Of course everyone was free to participate.

Since we were already dead tired at 7 pm, stretched out on our hotel bed, we wisely decided to go to sleep early so that we could start our Vespa trip fresh the next day. We did visit Argini e Margini the following weekend and it is definitely recommended to drink a cocktail on sultry summer evenings.

Il Giro Classico stage 1: Pisa – Siena

After a good night’s sleep, we enjoyed a delicious breakfast at Hotel La Pace. The day before we were informed via the WhatsApp group at what time we could drop our luggage in the van and when we could pick up our Vespa. Those who preferred to drive individually could leave a little earlier.

Arriving at The Vesparent we saw a red Vespa with our name on it. Not much later, Célia came to attach our GPS to the Vespa and gave us some more instructions on how to drive the Vespa. I left the driving part to Jan, because I’m not the best driver.

And then we could leave. It felt a bit awkward at first and certainly to drive directly into such a city as Pisa, but once we reached the quieter roads, we could cruise completely relaxed.

Piaggio Museum

The first stop was the Piaggio Museum in Pontedera. This town is the cradle of the Vespa. And therefore not entirely surprising that the Piaggio Museum is devoted to this iconic two-wheeler. The museum showcases several collections related to Italian-made engines and design.

The most impressive for me was the Vespa collection where you can admire the models from 1946 to now. It’s really nice to see that full evolution side by side. And it probably comes as no surprise when I say that the oldest models are my absolute favorites

San Gimignano

Between the winding roads, rolling hills and vineyards, we could see the picturesque town of San Gimignano with its 14 medieval towers appear on the horizon. What a beautiful sight!

Arriving at the town, it took a while to find a parking spot along the historic city walls. Walking into San Gimignano is like stepping back in time. It was lovely to stroll through the narrow alleys where we occasionally slipped into one of the many shops where they sell local products as souvenirs. We could also enjoy beautiful views and of course admire the impressive towers!

These towers were built between the 12th and 14th centuries by wealthy families to further highlight their wealth. At one point, San Gimignano even had 72 towers. It is the best preserved medieval town in Tuscany and is therefore even on the UNESCO World Heritage List.

The only downside is that it can get quite busy. The many visitors consist mainly of day trippers. So if you stay just a little longer until about 5 pm, when the day trippers return home, the charm of the town returns. Then it’s time to buy a delicious gelato at Gelateria Dondoli without long queues. This is said to be the best gelateria in town. Gelateria Dondoli’s gelato has won several awards. After tasting it myself, I can only recommend it. We took a seat on the steps of Piazza Duomo in the shade. What a wonderful moment! This here is what traveling is all about for me, enjoying the moment.

On the way from San Gimignano to Siena we were treated to breathtaking views. Because the sun was already a bit lower in the sky, the countryside turned completely gold.

Siena

Once we arrived at Hotel Italia, our hotel in Siena, we decided to freshen up quickly and head into town while it was still light. Because the hotel is a bit further from the center of Siena, we took the Vespa. We drove to Basilica di Santa Maria dei Servi where we easily found a parking spot. From this point we already had a beautiful view of the Duomo di Siena.

Through the narrow, winding streets we made our way into the heart of Siena. We passed super cozy restaurants, bars, boutiques and of course the typical gelaterie. What an atmospheric city! I was immediately in the mood for a tasty apéro, but I wanted to admire the Duomo di Siena first.

And that was a good decision. As we approached the Piazza del Duomo, we were momentarily overwhelmed. What a dazzling building, the shapes, the colours, the details, … Really beautiful! The light was just right and it was fairly quiet, so we took some time to take pictures.

Unfortunately, The Cathedral was already closed. You can visit it during opening hours for a fee and inside you’ll find sculptures by Bernini, Donatello and Michelangelo. So if you also want to admire the interior, you have to be here before 5 pm.

Then we walked along the famous Piazza del Campo, one of the most beautiful medieval squares in the world. The eye-catcher here is definitely the imposing Palazzo Pubblico, considered the most elegant Gothic palace in Tuscany. Today this building serves as the town hall of Siena and also houses the Museo Civico where you can admire the beautiful, preserved frescoes of the building.

The atmosphere in Piazza del Campo was quite lively. The edge of the square is filled with numerous terraces where you can enjoy a drink or a bite. It was very busy, so we decided to return along the narrow alleys and find a cozy restaurant to eat.

Finally, we ended our evening on the terrace of Ristorante San Domenico where we dined with a fantastic view of the Duomo di Siena. I couldn’t have asked for a better ending to my visit to this magnificent medieval city.

Il Giro Classico stage 2: Siena – Florence

On day 2 of The Vespa Trip we drove from Siena to Florence through the beautiful Chianti wine region. This was by far my favorite route of the entire trip because here you can experience the absolute, rural Tuscany. A landscape of vineyards as far as the eye can see, historic castles, winding (sometimes dangerous) dirt roads and charming medieval towns. It speaks for itself that we stopped here about 100 times to take pictures.

Radda in Chianti

It was already noon when we arrived at our first stop, Radda in Chianti, the official capital of the Chianti wine region. Jan was very hungry. And when that happens, we must first find something to eat. After Jan’s stomach was filled and he was able to function normally again, we explored this charming, historic town. In the narrow streets and alleys you will find many traces of the Middle Ages. Much of the city walls that have been preserved date back to the 12th century.

Greve in Chianti

After Radda in Chianti we entered the province of Florence where we took a break in Greve in Chiante. This lively city is known for its triangular market square. On this square you can admire the bronze statue of Giovanni da Verrazzano, the discoverer of the harbor of NYC, about which I will tell you more later. The market square is surrounded by colonnades to protect visitors from the weather. Here you will find many local restaurants and wine bars where you can taste the Chianti wine.

We only did a short walk through the city center, because we preferred to taste wine at a local wine estate. I found it a very pleasant town to stroll around in. And if you’re really passionate about wine, you can also visit a wine museum here.

For a wine tasting we could go with the group to Montecalvi, but we didn’t make it to the agreed time because we stopped too much along the way to take pictures. So we just randomly decided to visit a wine estate on our route to Florence. And that happened to be Castello di Verrazzano. Do you remember the name of the man from the bronze statue in Greve in Chiante? Yes correct! This was once his castle and wine estate.

Castello di Verrazzano

Giovanni da Verrazzano was born here in 1485 and was a true explorer. He discovered the port of NYC and other places along the East Coast of the United States. Legend has it that he was captured and eaten by native tribes. No one knows if this really happened. But this makes the wine estate all the more interesting for visitors.

The wine tasting is located in the castle on top of a hill. Just the road to it between the vineyards is already worth the trip up there. The castle has Etruscan roots and the vineyards of Verrazzano are said to have been producing wine since 1150.

You can opt for various guided tours, but you can also go for a wine tasting, drink or snack. Choose a spot on the terrace, where you have a great view of the valley. We each opted for a glass of wine and not an extensive tasting, because of course we still had to drive.

Florence

From Castello die Verrazzano it was just a short drive to Florence. This last part of the route through the Florentine hills was also formidable. We stopped briefly at San Miniato al Monte and Piazzale Michelangelo where you have the best views over the skyline of Florence. Piazzale Michelangelo is also a wonderful place to admire the sunset over this fantastic city with a drink.

We enjoyed the view for a while before going to the hotel. We quickly freshened up there. Since Hotel Plus is a fifteen minute walk from the center of Florence, we decided to give the Vespa a rest and walk. How wonderful it was to be back in this beautiful city.

We ate pasta on Mammamia’s terrace and then had delicious gelato as dessert overlooking Ponte Vecchio. In the end we didn’t make it too late, because the plan was to explore Florence further at sunrise the next day.

Il Giro Classico stage 3: Florence – Lucca

Florence

That morning we walked out of the hotel at 5:30 am sharp. I always love to wander through cities super early. At that time it is still very quiet and you have beautiful light. Getting up is sometimes a bit difficult, but most of the time it is really worth it. Also this time it was super satisfying. We had the historic center of the city, except for a few early birds, to ourselves. This way we could visit the few popular sights in Florence in peace.

We returned in time for breakfast and then took the Vespa towards Lucca. Navigating during the morning rush hour in Florence was quite scary. But once back on the smaller roads it went smoothly. We made our way to the town of Vinci.

During the route we once again enjoyed dazzling panoramas. Vinci is located at the foot of the Montalbano. This region is characterized by a hilly landscape with many olive trees, vineyards and forests.

Vinci

The town of Vinci is named after Leonardo da Vinci who is said to have been born here. In fact, he was born in a small hamlet outside the village. You can still visit his birthplace. It is arranged as a small museum.

In Vinci you can visit the church of Santa Croce where Leonardo was baptized. You can even admire his baptismal font there. In the village there is also a museum completely dedicated to Leonardo da Vinci. You can view many of his inventions here.

We also found Vinci a very pleasant town to take a break. We strolled through the charming alleys, bought some souvenirs and ate lunch on a terrace. Then we continue our route towards Lucca. On the way from Vinci to Lucca passed gigantic sunflower fields. Unfortunately they weren’t in bloom yet. We also passed the impressive Aqueduct of Nottolini.

Lucca

In the afternoon we arrived at hotel Carignano just outside Lucca. We had already been informed that the hotel had a nice outdoor pool, so we eagerly took advantage of it. We enjoyed a few hours of sun and water fun with, how could it be otherwise, a delicious aperol.

After this relaxing afternoon we took the Vespa to Lucca. There we went for dinner with a group of friends at l’isola che non c’era. Highly recommended if you like hearty meat dishes. A gelato for dessert could, of course, not be missing. And finally we ended the evening with a nightcap at the hotel bar.

Il Giro Classico stage 4: Lucca – Pisa

Lucca

Before starting our route for the day, we decided to go to Lucca for a while. We thought this was such a pleasant city. And while we enjoyed the night before so much, we felt like we hadn’t explored Lucca enough. We took a brisk morning stroll through the charming streets of the city and checked out the best things to do in Lucca.

Lucca is still completely walled today. You can enjoy a lovely walk on the wall, and you also have a beautiful view of the city. Some other special sights that you should not miss are the oval Piazza dell’Anfiteatro. This extremely charming square used to be a Roman Amphitheatre. Hence its curious, oval shape.

The Basilica of San Frediano is also worth a visit. Here you can admire the monumental mosaic on the facade.

And then in the middle of the city you also have the unique Guinigi Tower, where trees grow on the top. You can also climb it, but unfortunately we didn’t have time for that.

During our walk we also came across a construction project near the historic market hall where art is now exhibited.

After our visit to Lucca we took the Vespa to our next destination.

Ponte della Maddalena

The last stage of ‘Il Giro Classico’ was very surprising. We were introduced to another side of Tuscany. The rolling hills gave way to green mountain landscapes and rivers. We followed the river to Ponte della Maddalena, also known as the Devil’s Bridge. This beautiful medieval bridge dates back to the 11th century and is the subject of several legends.

Saint Julian, the master builder of the bridge, is said to have made a pact with the devil to speed up construction. In return, the devil would get the soul of the first living creature to cross the bridge. Saint Julian consulted a priest. He advised him to send a pig/dog over. (There are different versions.) And thus the devil lost to Saint Julian and would still be furious to this day.

Perhaps so furious himself that he made sure there was almost no water in the river when we went to see the bridge. But even without water it remains an impressive construction.

Montefegastesi

We continued along the river and then into the mountains on our way to Montefegastesi. As tipped by the guides of the Vespa Trip we stopped in Bagni di Lucca at the local supermarket, to buy some food for a picnic. There are no shops in Montefegastesi.

Then we made our way with the Vespa to the top of the mountain through winding roads and hairpin bends. The roads were shaded by the many green trees that grew on the edge. Very refreshing on this hot day. Before entering Montefegastesi, don’t miss the spectacular viewpoint over this mountain village.

Just before the entrance of the village there is parking to leave your Vespa behind. We arrived in Montefegastesi just after noon. It was as if this town had been completely deserted. There was not a soul to be seen. We climbed the steep roads to the highest point of the city while enjoying the blissful tranquility. Arriving at the highest point you can enjoy a panoramic view. We decided to have a picnic here.

Secret swimming Oase

After a delicious picnic we moved on. On the way back there is a secret spot somewhere where you can swim in the river. We received the coordinates through the WhatsApp group and went to have a look. We parked the Vespa at the edge of the road and found a hidden suspension bridge over the river. When we crossed it we could easily find a spot along the bank of the river to relax and take a refreshing dip. The water was very cold! But it was so welcome on this hot day. We stayed for a while to enjoy this piece of untouched nature.

Pisa

Still reminiscing about this blissful moment, we drove on to Pisa in one ride. Driving into town, we stopped at a gas station. Because of course we had to return our Vespa with a full tank. At The Vespa Rent in Pisa we said goodbye to our little red friend, who took us to the most beautiful places in Tuscany for 4 days long, with a little heartache.

The Vespa Trip Tuscany — *photo @laurendegryse*

To end the evening, we went for dinner with the group at Ristoro Pecorino in the center of Pisa. After the a pleasant dinner everyone said goodbye and so our 5 day Tuscany road trip with the Vespa came to an end.

Want to stay a bit longer?

Can’t get enough of Tuscany after 5 days? Then you just stay a while! Explore the most beautiful sights in Pisa. Or spend a day relaxing by the sea. You can even extend your contract at the Vespa Rental in Pisa to cruise around a little longer with the Vespa at a cheaper rate. You can ask more info about that at the travel guides of the The Vespa Trip.

From Pisa you can also easily travel by train to other regions. In less than an hour and a half you are in the beautiful Cinque Terre where you can enjoy beautiful hikes between the 5 picturesque harbor towns with the most fantastic views. Or take a break and relax on Lake Garda! Do you prefer adventure? Then travel to the impressive Dolomites. The neighboring province of Umbria is also worth a visit! And the beautiful historic cities such as Florence, Verona, Milan and Venice are not far away at all.

This was our 5 day Tuscany road trip with the Vespa. We have enjoyed it to the fullest. I hope that I have been able to fuel your wanderlust to discover this beautiful region in Italy in an original and authentic way.

Did you feel like a Tuscany road trip with a Vespa? Or do you have any questions? Be sure to let me know in the comments below.

Thanks for reading!

Love,

Sarah