Tuscany by Vespa

This morning, you ride east through the beautiful Chianti countryside to Badia a Coltibuono, an atmospheric former Vallombrosan abbey founded in the 11th century in the wooded hills above Gaiole. After a short visit, you continue to the tiny walled hamlet of Vertine, followed by a coffee stop in Gaiole in Chianti. Back on the Vespas, you wind along quiet country roads through the villages and hamlets of San Sano, San Felice, and Monti in Chianti, surrounded by vineyards, olive groves, and classic Tuscan scenery. You stop for lunch beneath the imposing Brolio Castle, then walk up to explore its gardens and ramparts, with sweeping views across southern Chianti. A fascinating private museum traces more than 800 years of Ricasoli family history through personal objects, documents, and family artifacts. You then ride back to Radda, where there is time to relax at the hotel spa—or indulge in a superb gelato at Bar Sandy. Tonight, dinner is at the local butcher shop, where the star of the show is Tuscany’s legendary Bistecca alla Fiorentina. The Ride 84 kms/52 mi. Overnight Radda. Hotel, breakfast, and dinner included. 

This morning you wind your way to the village of San Gusmè, which has been inhabited since the 8th century. A short walk around its medieval walls rewards you with gorgeous views across a sea of vineyards. You then ride south into a completely different landscape, leaving the green, wooded hills of Chianti for the wide-open spaces of the Crete Senesi. Those who have seen Gladiator or The English Patient may recognize this starkly beautiful countryside of rolling clay hills, isolated stone farmhouses, and solitary cypress trees. Stop for lunch at a quaint local trattoria in the lovely hamlet of Chiusure before continuing to Montalcino, a magnificent hilltop town and home of one of Italy’s greatest wines, Brunello di Montalcino. Check into Hotel dei Capitani, a charming, family-run hotel with sweeping views over a patchwork of vineyards, olive groves, stone farmhouses, and tiny hamlets. Tonight, enjoy dinner at Osteria di Porta al Cassero, a welcoming family-run trattoria in the heart of Montalcino. The Ride 87 kms/54 mi. Overnight Montalcino. Hotel, breakfast and dinner included.

Today your guide will lead you on a gorgeous ride through the wonderful Orcia Valley, one of Tuscany’s most beautiful landscapes—a rolling sea of wheat fields, vineyards, cypress-lined lanes, and ancient hilltop villages. Your first stop is the magnificent Abbey of Sant’Antimo, a serene Romanesque church nestled among olive groves beneath Montalcino. From here, you climb back onto your Vespa and follow wonderfully scenic country roads past Castiglione d’Orcia and the medieval fortress of Rocca d’Orcia, before winding across the valley to the tiny walled village of Monticchiello. Your morning ride ends in Montepulciano, where you have free time to explore its handsome Renaissance streets and enjoy lunch at your leisure. In the afternoon, you saddle up again and ride to Pienza, the jewel of the Val d’Orcia, before making the final panoramic ride across the hills to Montalcino. You can relax at the swimming pool or wander amongst Montalcino's quaint streets, from wine bar to wine bar before dinner in the village.The Ride 92 kms/58 mi. Overnight Montalcino. Hotel, breakfast, and dinner 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 take a taxi to the train station, which is a few kilometers outside the city center.  Breakfast included. 

Please note: Depending on your tour's departure date, some itinerary details 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 replacing something that no longer meets our standards.  We always aim to provide you with the best possible experience so you'll come back for another tour! We will let you know of any changes to the original itinerary before departure.