Chianti

From 2 PM onwards, you are welcome to check in and settle into the hotel’s refined comfort. Your Vespa will be ready for you the next morning. Later that day, your guide will personally welcome you and provide a detailed introduction to the journey ahead.

Spend the afternoon at your leisure, unwind by the pool, stroll through the nearby village, or simply take in the beauty of your surroundings.

New to riding a Vespa?
For Vespa Trippers without prior experience, we recommend our Start to Vespa session, a relaxed and confidence-building introduction to ensure you feel fully at ease before setting off.

On your second day, the journey truly begins. You’ll leave the tranquil surroundings of Impruneta behind and ride into the rolling hills and winding roads that define the Tuscan countryside.

Your first stop is the charming town of Montespertoli, known for its peaceful vineyards and panoramic views, the perfect setting to ease into the rhythm of the road.

From there, continue on to Certaldo, a beautifully preserved medieval village perched on a hilltop. Stroll through its cobbled streets or take the funicular to the historic upper town for a glimpse into Tuscany’s past.

Next, the road leads you to the iconic towers of San Gimignano, often referred to as the “medieval Manhattan.” Soak in the skyline, and don’t forget to stop for a photo or a scoop of gelato in the town’s picturesque piazza.

After a full day of exploration, you’ll make your way back to the hotel, passing through more of Tuscany’s postcard perfect landscapes. The evening is yours to unwind, whether by the pool, at the bar, or sharing stories with fellow travelers.

This day is a true highlight of the journey, a day where every turn reveals another postcard view. Leaving Impruneta behind, you’ll ride deep into the legendary Chianti region, renowned for its timeless beauty, gentle hills, and world-class vineyards.

Your route winds past ancient castles and sleepy hamlets, eventually leading you to a first stop in Lucolena, a quiet village tucked away in the hills, where the pace slows and the scenery is unforgettable.

From there, continue toward Radda in Chianti, the historic capital of the region. Take a break to enjoy the atmosphere, perhaps with a coffee on a sunlit terrace or a short stroll through its stone streets.

The road then takes you to Greve in Chianti, one of the area’s most beloved villages. Its central square is lined with arcades, artisan shops, and historic wine merchants. Be sure to stop by Macelleria Falorni, one of the oldest butcher shops in the world, a true institution of Tuscan culinary heritage.

After a day rich in scenery, culture, and flavor, you’ll head back through the hills to return to the hotel, with maybe a few local delicacies in tow.

Today it begins with a scenic ride to Fiesole, a peaceful hilltop town just above Florence. Known for its Roman amphitheatre and breathtaking views over the city, it’s the perfect spot to pause and take in the grandeur of the Tuscan landscape before heading into the city.

From Fiesole, you’ll make your descent into Florence, arriving in time to enjoy a full afternoon in one of the world’s most iconic cities. Whether you choose to wander through Renaissance masterpieces, shop in artisan boutiques, or simply sip an espresso on a sun-drenched piazza, Florence promises a truly unforgettable experience.

Before heading back, make a final stop at the famed Piazzale Michelangelo. From here, the sweeping views across Florence, with the Duomo, Arno River, and terracotta rooftops, are the perfect farewell to the city.

As the sun sets, ride the winding roads through the Florentine hills back to the hotel, soaking up the last golden moments of your Tuscan adventure.

You will be able to enjoy a last breakfast in the hotel. From now, it’s up to you to decide to continue your journey in Italy or return home.

Here, you can choose the Late Drop-Off option (€ 50 per Vespa), to keep your Vespa until 2 pm and take it for one last farewell drive to say goodbye to your Vespa and the beautiful region.