The Tuscan Odyssey tour is a private luxury tour through some of the best parts of Tuscany including Siena, Orbitello, Montepulciano, Cortona, Pitigliano and many of it's least traveled roads. The itinerary is ideal for a broad range of riders, you can choose to ride the distance from town to town, or for those that want to ride more we customize the routes to include longer distances and climbing. The tour starts in the town of Orbitello which is on the Etruscan coast of Italy one and a half hours north of Rome. You can arrive in Florence or Rome for the start of this tour. Your group is picked up from the airport in a private car and taken to the start of the tour where your bikes are waiting. We supply Bianchi road bikes for our bike rentals. Being a private tour there are plenty of opportunities to customize the itinerary some to include additional wine tasting or cooking classes.

Package Includes

• Fully supported with superior accommodations

• Support Van

• Local guide

• Granfondo Cycling Tours kit included

• Breakfasts and dinners included

• Rental bike included (Bianchi road)

Tour Itinerary

Arrive in Florence or Rome for the start of this tour. Your group is picked up from the airport in a private car and taken to the start of the tour where your bikes are waiting. After arrival your group can take a ride around Orbitello and its picturesque national forest.

Today you will ride inland though rolling hills and countryside to Pitigliano. Pitigliano seems to have stepped out from a fairytale and appears to have grown from the stone of this wildly beautiful area, bounded by green valleys crossed by the Lente and Meleta rivers. The high walls of volcanic tufa, are carved by a thousand caverns, and tower-houses that heighten the picturesqueness of the medieval town. It has several stores, cafés and restaurants. This past becomes present while walking the old streets and admiring the ancient houses and visiting the famous Jewish ghetto. The large and active Jewish community, dating from the 15th century, has prompted the name “Little Jerusalem” for this splendid village. Wine tasting in Pitigliano is a must, the wines from the surrounding vineyards are superb.

After breakfast we will ride into the heart of the Val d’Orci, dotted with cypress trees and traversed by the ancient Roman road the Francigena. This area is one of Tuscany’s best-preserved natural wonders. It has become known all over the world as the classic Tuscan landscape. The UNESCO World Heritage List recognizes Val d’Orcia’s extraordinary beauty and its inspiration and prominence in landscape painting.  Important films like the Oscar winners The English Patient, La Vita è Bella, and Gladiator were shot here, and most recently Under the Tuscan Sun, extending Val D’Orcia’s beauty and influence into cinematic history. Castel del Piano is a very lovely town along the base of Mount Amiata.

Today we ride through rolling hills and vineyards to the walled hill top town of Montalcino. "From this height, you are left breathless by the panorama," recounted Gabriele D'Annunzio in his great work "The Prank of Buccari," he defines Montalcino as the "window sill of the Apocalypse. On a clear day with naked eyes we see Corsica, the island of Elba, the island of Giglio, the Tyrrhenian Sea, the Apuane Alps, the Abetone, the Consentine with the Sluices of Verna and the Terminillo. Still closer, we see the cities of Siena, Pienza and Montepulciano. We see the long sleeping volcano Monte Amiata casting its shadow over our valley." Here is produced some of Italy's best wines. The brunello wines are made exclusively from the brunello grape. This is an area that no wine lover visiting Italy will want to miss.

Montepulciano is Tuscany's largest hill top towns. Montepulciano, with its medieval alleyways and plethora of Renaissance palaces and churches, is a great place to have lunch. The fields around the town produce a violet-scented, orange-speckled ruby wine called Vino Nobile di Montepulciano. This area has been known since the 8th century for its superior wine. In the 17th century Francesco Redi wrote his vino-praising poem, Bacchus in Tuscany, describing the vintage of Montepulciano as "The King of all wines," Vino Nobile.

Cortona is the beautiful romantic town made famous recently in the book, "Under the Tuscan Sun" by Frances Mayes. Cortona is surrounded by defensive walls, the foundations of which date back to the Etruscan period. Tightly-clustered medieval houses pack the slopes, leading upwards to an open green area where the hill is crowned by a Medici fortress, the Fortezza Medicea. This town is home to many famous painters who no doubt used the surrounding landscape for inspiration.

After a day riding in the Tuscan Country side you will arrive to pure luxury. Tonight we will be staying at Locanda dell'Amorosa. Prehaps there web site tells it best. "The location exudes an atmosphere of true serenity and sweetness and anyone exposed to it will be awestruck. Perhaps this feeling has been instilled by the generations that have loved and respected this village. Perhaps it is because in the last seven hundred years of existence it has changed owners only once. Each room has its own character and design. Rustic furniture of peasant origins is mixed with antique furniture, prints and paintings. Some, that open directly to the outdoors give the sense of having a place of one's own; others have a relaxing view of the typical Sienese countryside; yet other look out onto the complex's quadrangle and face the lodgings the peasants at one time inhabited. In addition to the extensive garden maintained and reserved for the guests' use, the hotel is surrounded by its own farmlands, vineyards, olive orchards, woods, and well - cultivated plains of corn wheat and sunflowers, rendering an ideal environment for walks in the countryside.

Surrounded by olive groves and vineyards, Siena is one of the most beautiful cities of Tuscany. The town is built on three hills and surrounded by well preserved walls. This town is filled with fine examples of Gothic architecture and has one of the world's most unique piazzas - il Campo. This piazza is the spiritual and virtual heart of the city where each year the neighborhoods of Siena compete with one another in the now world famous “il Palio” a bareback horse race around the square. Tonight we dine at a restaurant frequented by the locals and known for its exquisite cuisine.