Vespa Tour Tuscany: 5 Beautiful Cities for Your Italy Road Trip

You can spot San Gimignano from miles away, with those characteristic medieval towers rising dramatically above the landscape. There used to be 72 of these towers (yes, really!), now “only” 14 remain. The fascinating bit? These towers were actually a kind of medieval showing-off contest – the richer the family, the higher the tower.

Take a leisurely stroll along Via San Giovanni, the main thoroughfare of the town. Here you’ll find the most delicious local specialties: from the famous Vernaccia wine (which they’ve been producing here since 1200!) to saffron from the nearby fields. Don’t miss the Collegiata – a church filled with colourful frescoes that transport you back to medieval life. They’re like centuries-old comic strips!

San Gimignano ranks high among the best places to visit in Tuscany, especially for those seeking genuine medieval architecture.

Siena is one of those cities where you feel like you’ve accidentally stepped into a time machine. The famous Piazza del Campo, shaped like a shell, is the heart of everything. Twice a year, this square transforms into a wild horse racing track for the Palio – then the whole city goes absolutely mad.

The cathedral here is a must-see. With those striking black and white marble stripes, it looks rather like a giant zebra suit. The small streets that wind up from the square? Pure magic. They lead you to hidden piazzas and churches where you discover the real Siena.

While you’re in the area, ride over to Monterriggioni. This perfectly preserved medieval fort offers one of the most breathtaking sunsets in all of Tuscany. For anyone planning holidays to Tuscany, Siena should be at the top of your list of Tuscany Italy attractions.

Florence is essentially an open-air museum, but one where everyday life simply carries on. The gigantic Duomo naturally steals the show – that red dome peeks out above everything. And yes, the Ponte Vecchio with its historic shops is something you shouldn’t miss.

But the real Florence? You’ll discover that in the most beautiful spots just outside the centre. Take the Oltrarno district, on the other side of the Arno. Here you’ll find no tourist crowds, just authentic workshops where craftsmen still practise their trade. You’ll stumble across fresh pasta shops where grandmothers still make pasta by hand, and artists working from ancient towers.

Pro-tip for your Italy road trip: ride to Piazzale Michelangelo at sunset – that view over Florence is absolutely unforgettable.

Lucca is unique: it still has complete city walls from the Renaissance period. But instead of just preserving them as a monument, they’ve done something rather ingenious with them. The entire wall is now an elevated park where locals jog, cycle, or enjoy picnics. Brilliant, isn’t it?

The most special spot? Piazza dell’Anfiteatro – an oval square that exactly follows the shape of the ancient Roman amphitheatre that once stood there. And then there’s the Guinigi tower, with real oak trees growing on the roof (yes, you read that correctly).

Lucca’s narrow streets are full of surprises and restaurants where grandmother still stands in the kitchen. On your motorcycle touring route through Tuscany, Lucca offers a refreshing change from the bigger tourist hotspots.

Let’s be honest: everyone comes for the leaning tower. And yes, it is rather impressive. But Pisa has so much more to offer! The Piazza dei Miracoli (where that famous tower stands) is actually one big architectural celebration, with a cathedral and baptistery that are at least as spectacular.

The student district tells a whole different story: here you’ll find cosy cafés and restaurants where you can eat fantastically for normal prices. And in the evening? You really must walk along the Arno. That small Gothic church by the water, the Santa Maria della Spina, is a jewel that most tourists miss.

When planning your scooter tour in Italy, don’t just dash in for a quick photo with the tower – Pisa deserves at least half a day of exploration.