The tour picks up at 9:30 a.m. from the Hotel Orto de’ Medici, our recommended hotel in Florence.  We then have a 1hr 15 min transfer to the village of San Sano. After a safety talk and a little bit of practice we begin our ride through the glorious Tuscan countryside. Oak forest, olive groves and vineyards set the bucolic scene. Hilltops are punctuated by castles, villas, and ancient walled villages. Our red Vespas take us to the medieval "borgo" of Castagnoli where we stop to enjoy your first taste of Tuscany’s famed cuisine. Afterwards, a short ride takes us to imposing Brolio Castle,  home to the noble Ricasoli family since 1141. We visit the castle’s park and gardens and a fascinating private museum which displays family artifacts that span the 800 years in which the Ricasoli’s have inhabited Brolio. We finish our day in the charming hilltop village of Radda in Chianti and check into the four-star hotel Palazzo Leopoldo (or similar). We have a glass of prosecco in the piazza before dinner in a local trattoria. Overnight Radda. Transfer from Florence, hotel and dinner included.

This morning you ride west towards the hilltop village of Castellina in Chianti where you have time to walk along the  ancient vaulted street which was part of the medieval fortifications. You'll have time to peruse boutiques and shops  before hopping back on your Vespa for a super scenic ride amongst the rolling olive groves and vineyards of Chianti  Classico fame. Stop for a coffee break in the village of San Donato before continuing on to Panzano for lunch at a small  family-owned winery. The setting is truly magnificent as you look out over a patchwork of vineyards, olive groves, and  forests adorned with stone villages, farm houses, and villas. The afternoon unfolds with a ride to the Badia a Coltibuono  to visit the ancient abbey where you see the 500 year old cellars, as well as the gardens, cloisters, and frescoed rooms of the abbey. Return to Radda and relax at the hotel spa or enjoy a superb gelato  from “Antica Gelateria.” We reconvene for an aperitivo and then dine in a lovely restaurant in town. Overnight Radda. Hotel, breakfast, lunch and dinner included.

This morning you ride through olive groves and chestnut forests to the highest point in Chianti for breathtaking views. We then drop down to the village of San Gusmé, which has been inhabited since the 8th century. A short walk around the medieval walls rewards you with gorgeous views over a sea of vineyards. We then ride south into a completely different terrain as we leave the green wooded hills of Chianti for the wide-open spaces of the Crete Senesi. Those who have seen the films “Stealing Beauty” or “The English Patient” will recognize this starkly beautiful landscape of barren rolling hills topped by stone farmhouses and solitary cypress trees. Stop for lunch at a quaint local trattoria in the lovely hamlet of Chiusure. After lunch, ride to Montalcino, a magnificent hill top village and home to one of Italy's finest wines, "Brunello di Montalcino". Check into the Vecchia Oliviera, a charming small, family run hotel featuring epic views over a patchwork of vineyards, olive groves and stone farmhouses and hamlets. Tonight’s dinner is at the Grappolo Blu, a lovely trattoria with an incredible wine list featuring decaces old Brunello, should you wish to treat yourself. Overnight Montalcino. Hotel, breakfast and dinner included.

Today we have a gorgeous ride through the wonderful Orcia Valley, where you’ll see the iconic rolling hills famous from postcards and calendars. Take small roads that wind their way up, over, around, and between tiny villages such as Monticchiello, where we’ll stop for a stroll and a coffee break. Then ride for another hour or so to the hilltop town of Montepulciano, renowned for its Vino Nobile wine. You have time to explore the city's colorful streets and Renaissance palazzi, do a bit of shopping, and then stop for lunch at one of the many restaurants. Afterwards, ride to the perfect Renaissance town of Pienza, which was designed and built by a local boy who made it big: Pope Pius II, who decreed that his home town was to become a center of art and humanistic scholarship. It was completely rebuilt between 1459 – 1462 according to the latest Renaissance styles. You then have a leisurely ride back to your lovely hotel in Montalcino where you can relax at the swimming pool are wander amongst Montalcino's quaint streets, from wine bar to wine bar. We walk to dinner in the village. Overnight Montalcino. Hotel, breakfast, and dinner included.

Our last ride takes us along one of the most scenic roads in Tuscany, past Trequanda and the ancient walled village of Asciano. Eventually you reach Siena, where you'll drop off your trusty Vespa and head into the historical center. Siena's Gothic architecture was left perfectly preserved after the city was taken over by Florence in 1585, and its main square, “Il Campo,” is considered by many to be among Italy’s finest. Enjoy lunch in town and then learn all about the famous bareback horserace known as "il Palio" from our local guide, who will also take us to visit the cathedral and its medieval treasures. You have free time this afternoon to explore Siena's colorful shops and backstreets, and also time to rest at our hotel before enjoying a final dinner together in town. Overnight in Siena in a centrally located superior three-star hotel. Breakfast, dinner and hotel included.

Depart at your leisure this morning. The bus station is an 8-minute walk from the hotel and you can get buses to Florence (departing every hour, the journey takes 1 hr 15 mins) or Rome (3 hrs). For rail connections, you can get a taxi to the train station, which lies a few kilometers outside of the city center. Breakfast included.

Please note: According to the departure date of your tour some details of the itinerary may change. This is because we make discoveries whenever we run a tour. Sometimes they are good, like a wonderful new wine bar that we want to take you to, and sometimes bad, like a road has been washed away. We, therefore, sometimes change our itinerary to improve it by adding something new or substituting something that is no longer up to our standards.  We always aim to provide you with the best possible experience because we want you to come back for another tour! We will let you know before departure of any changes to the original itinerary.