Bike Tours in Italy!

Tuscany and Umbria

This tour has been carefully designed to capture the essence of the Tuscan and Umbrian experience (think of places such as Siena, Montalcino, Pienza, Spello and Assisi!). We have selected absolutely stunning accommodations, include superb meals, wine tastings, personalized walking tours of Siena and Assisi…and you will be led by talented, engaging and very experienced bilingual Italian guides, whose intimate knowledge and love of all things, places and people Italian will assure that your vacation is a visual, culinary, and cultural delight.

The hotels are exquisite. Each was carefully selected by us not only for their superior quality but also to ensure that you are always staying within the city walls so you can stroll the narrow cobbled streets, visit the shops, see the sights at your leisure, and truly immerse yourself in all the day-to-day Italian experiences that make this a true adventure. Il Chiostro del Carmine is one of the few small elite hotels within the walls of Siena; every room at Hotel Dei Capitani in Montalcino offers endless views over the Tuscan countryside; Hotel Relais Il Chiostro de Pienza, located in the heart of the Renaissance town of Pienza, is surely one of Italy’s finest; and La Bastiglia, in Spello enjoys fame as both a superb hotel and as one of Umbria’s most highly acclaimed restaurants.

We have taken great care to develop a tour that offers you the full pleasures of the sunny and enchanting Tuscan countryside as well as visits to a delightful collection of small villages and towns. We travel through vineyards; past olive groves; and along narrow ancient roads lined with cypress. We wander the narrow alleyways of tiny medieval villages like Murlo; Montisi; Castlemuzio and Bevagna; listen as the monks sing at Sant'Antimo; gaze in awe as we tour the Basilica di San Francesco in Assisi; relive movie scenes from "The English Patient" as we stroll the grounds of Santa Anna in Camprena; lounge in the thermal pools of Bagno Vignoni; and delight in a visit to the elegant Castello Banfi estate and vineyards.

We are also the fortunate beneficiaries of the Italian obsession with all things culinary. Abundant regional produce, wild game, local mushrooms, olive oil, pecorino cheese, local truffles, and homemade pastas, all complemented with the finest local wines (and a superb wine tasting event!) assures that we will be treated to the finest regional cuisine imaginable.

We designed this route fully mindful of the need to accommodate the energy and desires of all types of riders. Montalcino and Pienza are both on hills and we will be encouraging some to ride in our carefully positioned van the 2-3 last miles into town. Likewise, on Day 3, there are a few challenging miles before arriving at the abbey at Sant'Antimo. Due to these exceptions (all avoidable with a short van ride), and despite the fact that the vast majority of the cycling is "Easier to Intermediate", we think the tour, as a whole, is appropriately rated "Intermediate."