A Vespa trip through Tuscany: drive this epic itinerary in 8 stops

Are you ready for one epic road trip that takes you behind the wheels of Italy's most famed mode of transportation? The start of your exciting TravelBase Vespa trip through Tuscany begins in the famed city of Pisa. Upon arrival, you’ll be welcomed at your hotel where you can check into your room, and then be introduced to the Vespa Trip guides. From there, it’s time to explore Pisa as an exploratory amuse-bouche before you go off riding!

The city itself is prominent for the Leaning Tower of Pisa, which is a stunning landmark that is unmissable. A freestanding bell tower that is famous for its unintended tilt, it has continued to lean over the centuries due to various factors from the soft ground it was built on. To this day, the Leaning Tower of Pisa is considered a masterpiece of Romanesque architecture and is a UNESCO World Heritage Site.

Pisa is also home to other notable landmarks and cultural attractions that you can explore, such as the Pisa Cathedral, the Pisa Baptistry, and the Pisa Museums. By evening time, you’re invited to have a classic Italian drink at a local bar with all of the Vespa Trippers and guides before you embark on your journey the next day!

Now, the next day is when your Vespa Trip through Tuscany truly starts, as you’ll get to strap on your helmet and take a step to the pedal of your shiny pastel-colour Vespa. Yep, this is the moment you'll be handed keys to the kingdom - well, your fantastic two-wheeler kingdom, that is. Right away, you’ll set off on a journey on your new Vespa that will have you zipping through the winding roads that adorn the Tuscan landscape, heading into the idyllic countryside where the vineyards meet the olive groves.

While you’re riding your Vespa on your way to Siena, the Medieval Tuscan city is only the endpoint as there are plenty of enriching sights to explore along the way. Your first stop will be the artisanal town of Pontedera, where the emblematic Vespa itself was born. Here, you can visit the Vespa museum (Museo Piaggio) for free.

Pontedera, with strong roots in Italy’s industrial history, has an artistic soul on the Era and Arno rivers. The whole city is like an open-air museum, from the 100m long wall covered by a mosaic aka the Enrico Baj to the designer benches that welcome anyone in Piazza Garibaldi.

After the birthplace of the Vespa in Pontedera, you’ll cruise for about an hour on your Vespa through the ancient countryside where the sky meets the swaying meadows, dotted with Parish churches and Tuscan villages. Take in the sights of what makes Tuscany just so romantic and peaceful - from the neatly planted vineyards to the pebble roads, no wonder why it's so easy to fall in love with Central Italy. On one of the many scenic hills of this region, you’ll then arrive at a walled Medieval town known as San Gimignano.

San Gimignano has, hands down, one of the most breathtaking skylines in the world. Tall toppling stone towers will automatically daydream you away to the Middle Ages, and as you roam these streets that haven’t changed their design much since then, you’ll feel like you’ve stepped through an actual Renaissance painting itself.

This is the town to have a glass of Vernaccia, a white wine that is produced within the surrounding hills of San Gimignano itself. Since you’re here just in time for lunch, you can pair your wine with some of the local’s favourites - like homemade pici pasta, Ribollita (a thick vegetable and bread soup), and crespelle with asparagus and ribola cheese.

End your first day by arriving in Siena, about a 45-minute drive from San Gimignano. Siena is a Tuscan city that will easily bewitch its visitor with a true love-at-first-sight feeling. Located in the heart of Tuscany, Siena is quintessential what makes Tuscany much loved: its sensational art collection, architecture that weaves through its contrade (distinctive urban districts) and a history that reaches back further than the Romans - all the way to the Etruscans.

Siena is already prominent for its annual horse race, the Palio di Siena, which takes place in the city's main square, the Piazza del Campo. There, in the centre of town - you can wander around the Piazza del Campo, and soak up what is considered one of the most beautiful squares in all of Italy. The square is surrounded by soaring medieval buildings, including the Palazzo Pubblico, which is home to the city's government.

For dinner, sit out on one of the many places lining the piazza (unlike other landmark dining locations, most of the ones here aren’t actually a tourist trap), grab a coffee or gelato as dessert, or just people-watch and enjoy the jovial atmosphere as the locals do. It makes a simple yet delightful way to end the evening.

You didn’t think you’ll embark on a Vespa adventure in Tuscany without diving into one of the world’s most beloved wine and its region, did you?

Sprawling between the gently sloping hillsides of Siena and Florence is Chianti, a region within Tuscany known for its namesake type of wine. Made from the Sangiovese grape, the Chianti region produces both red and white wines. But it is the red Chianti Classico that it’s best known, which is a full-bodied wine with flavours of irresistible cherries and that masculine leather.

Even on your Vespa ride, you’ll notice countless vineyards ebbing and flowing alongside the road until you reach Radda. Radda is the capital of the Chianti region and will give you what an authentic charming Italian town feels like - without the tourist crowds. You can check out La Bottega di Giovannino, a petite wine bar located in town. There’s also Bar Ucci, which has a special focus on Chianti Classico.

Another pit stop close by is Greve, a Medieval town where you can explore artisanal local shops like the Macelleria Falorni (locals say that this is the oldest butcher shop in the Western world). Also don’t miss out on the triangular-shaped square of Piazza Matteotti!

The cradle of the Renaissance, a whole historic centre that’s been crowned a UNESCO World Heritage Site, all located on the Arno river itself… It can only be the golden child of Central Italy and the capital of Tuscany, Firenze. Also known as Florence, a city that is steeped in old-world romance, filled with legendary art that has influenced Western civilization and where Tuscan food is as mouth-watering as it could get since the cooking is from seasonal ingredients grown in the Florentine countryside. For any traveller, Florence is a force to be reckoned with.

A Vespa road trip through Tuscany just can’t be completed without a stay in Florence. With tons of sights to see - you’ll have your pick all around the city. The Uffizi Gallery rivals Paris’ Lourve Museum, and if you go early in the morning, it’ll feel like you have most of the art museum to yourself. Or, visit the original sculpture of David that’s located in the Accademia Gallery of Florence. Roam within the walls of the majestic Cathedral of Santa Maria del Fiore. Take a stroll down the arched bridge of Ponte Vecchio. And be sure to make your way to our favourite spot in the whole city, Piazzale Michelangelo where you can see all of Florence from its grand open balcony.

When it’s time, you’ll continue your Vespa trip out into the Florentine hills, where the Tuscan landscapes will roll out in front of you. About 45 minutes outside of the city, you’ll arrive at Lago Le Certane, to have a breather on the lake before driving to Vinci. Vinci, while small in size, is rather impactful since one of Italy’s most famous people in the world originates from here - Leonardo da Vinci.

Lucca has this small-town feel for a Tuscan city, that offers a close-to-the-sea alternative to its hilly Siena and Florence. It's easy to overlook Lucca for first-timers in Tuscany (especially since Florence and Siena get so many hearts swooning away). Still, the humbleness and local scene of Luca is what adds to this city's allure and why it's worth uncovering on this Vespa trip.

Explore the well-preserved historic centre of Lucca, which is surrounded by ancient walls. The walls, which were built in the 16th century, are now a popular place for walking and biking and offer stunning views of the city and surrounding Tuscan countryside.

Lucca’s historic centre is also home to many beautiful churches, such as the Basilica di San Frediano and the Cattedrale di San Martino, as well as the Puccini Museum, which is dedicated to the famous composer.

When you’re hungry, definitely cosy into one of Lucca’s trattorias with traditional Tuscan cuisine heavily influenced by the region's rich agricultural history. Look out for classic dishes like pappardelle al sugo di cinghiale (wide pasta noodles with wild boar sauce) that are cooked in Chianti Classico wine.

The fifth and last day of the Vespa trip in Tuscany is where you can choose between spending the day at the beach - yep, few actually know that Tuscany has pristine beaches to be discovered! Or you can continue on driving your Vespa to Bagni di Lucca.

Not that we need another reason to be absolutely smitten with Tuscany, but in the area of Bagni di Lucca is home to several thermal baths. The most famous of these is the Terme Tettuccio, which is located a stone-throw away in Montecatini and offers a variety of treatments and therapies. You can visit them as a treat to relax and unwind, especially at the end of an adrenaline-fuelled Vespa tour!

From Bagni di Lucca, there’s also one last surprise on the Vespa trip. Closed off from the outside world and unbeknownst to many travellers in Italy is Montefegatesi. Along the route to Montefegatesi, you’ll be whisked away off the River Lima to swim in a secluded spot that’s not even indicated on the map! You can only find this authentic hidden gem via the GPS coordinates that TravelBase Vespa tours will secretly share with you.

To wrap up the Vespa trip, you’ll ride back to Pisa where you first embarked on this grand journey. It’s time to say goodbye to your new two-wheeled best friend and end this adventure that’s for sure one for the books.