Independent arrival in Perugia. Perugia’s stone alleyways link charming squared framed by Gothic palaces and friendly cafes. The main shopping promenade, “il Corso,” is the central artery while hundreds of narrow medieval streets wind around this ancient hilltop town. Perugia is the perfect introduction to Umbria’s vibrant contemporary culture which is rooted firmly in its glorious past. Meet your guide(s) at the train station at 2 p.m. and transfer to the countryside where we begin our first ride to the wine-producing village of Torgiano. You will have time to explore the town and the fantastic Lungarotti wine museum before continuing on to Bevagna, a beautiful walled village with Roman, Medieval, and Renaissance architecture. Our hotel, Il Chiostro (or similar), is a converted 12^th-century convent. Bevagna also boasts some excellent trattorias and wine bars where we will enjoy a drink before dinner at the Osteria Podestà. Overnight Bevagna. Let us know if you would like to stay the Saturday night in Perugia. We will be happy to recommend hotels. Overnight Bevagna. Hotel and dinner included.

Assisi rises dramatically on a hill beneath Monte Subasio in the heart of Umbria. Like so many Umbrian towns, Assisi has its own particular color, a rosy glow reflected from the pink hues of the locally quarried stone used in the town’s centuries’ old buildings. You will have time in the morning to explore Assisi and visit the basilica of San Francesco, famous for its 14^th-century frescoes depicting the life of St. Francis attributed to Giotto. A delightful afternoon ride takes you to the charming walled village of Spello past ancient olive groves. It is then a short ride back to Bevagna. Strong riders can do a challenging optional ride via Gualdo Cattaneo. Overnight Bevagna. Hotel, breakfast and dinner included.

Today we ride across the valley to the hillside village of Trevi for mid-morning cappuccino in the village square before heading into the rolling hills and vineyards that surround Montefalco, Umbria’s most prestigious wine-growing town. This afternoon we have a guided visit and tasting at one of the producers of the famed Sagrantino di Montefalco. The town itself is worth a visit. It sits high above the Clitumnus valley and was once a Roman garrison town and later a strategic fortress in the conflict between the Guelphs and Ghibellines. The 14^th-century ramparts that surround the village date from this period. Our home for the next two nights is the Hotel Degli Affreschi (or similar), a beautifully renovated noble house in the heart of the old town. This evening is a “free night” dinner so you can choose to splash out on a lavish meal or try some lighter fare at one of the town’s many trattorias. Overnight Montefalco. Hotel & breakfast included, dinner not included.

Today’s destination is splendid Spoleto. Ringed by Roman and Medieval walls and surmounted by an imposing 13^th-century fortress, it is one of Italy’s most beautiful towns.  A breathtaking gorge, verdant with holm oak forest, is traversed by a dramatic 1000-year-old arched aqueduct. The town’s narrow streets are lined with homes and shops whose origins go back to Roman, Lombard, and Medieval times. Our return ride meanders through Montefalco’s vineyards and appropriately we end the day with a tasting of the sought-after Sagrantino di Montefalco. Overnight Montefalco. Hotel, breakfast and dinner included.

Leave Montefalco this morning to head into the wild hills of Umbria. The ride takes us through a sparsely populated area, into tiny hamlets and villages and past imposing castles and villas, before dropping us back down to the valley beneath the perched town of Todi. Dramatically situated on the peak of a hill at a sharp bend in the Tiber river, Todi has for centuries been an important strategic city. Three sets of concentric walls date from Etruscan, Roman and medieval times, encircling the stone palaces and townhouses of the ancient city. Todi has one of the most beautiful squares in all of Italy, set between the 12^th century cathedral and the city's imposing public buildings, including the crenellated walls of the Palazzo dei Priori, the Romanesque-Gothic Palazzo del Popolo, and the Gothic Palazzo del Capitano. We dine tonight is in Todi's finest restaurant. Overnight Todi. Hotel, breakfast and dinner included.

Cross the Tiber river on the 14th-century Ponte Cuti bridge before starting a long but gradual climb up onto a high plateau. The views are stunning throughout the day. The ride continues through rolling country before a long descent towards Orvieto, which sits atop a pedestal of volcanic tufa rock surveying the Tiber valley. Like so many Umbrian towns, its foundations are Etruscan but its most prosperous period was during the Middle Ages when the Popes came to Orvieto to escape the summer heat in Rome. Orvieto's cathedral is widely considered to be one of the finest in Italy. Our hotel is located within the thick city walls. Overnight Orvieto. Hotel, breakfast and dinner included.

You can choose to do a relatively short ride out to the stunning village of Cività di Bagnoregio, which is perched precariously on a narrow plinth of tufa rock. From there, return to Orvieto to explore its underground city or continue biking to the lakeside village of Bolsena to make for a satisfying 70 km day. Both rides “feature” a steep climb from the base of Orvieto out to Porano and then pleasant, rolling countryside. The village of Bolsena has a beautiful medieval quarter dominated by the 13th century castle, and there are several good seafood restaurants around the lake. The return ride gives you an unforgettable view of Orvieto as the low afternoon sun glitters off of the mosaics that adorn the façade of the Duomo. Enjoy another fabulous dinner tonight at a local trattoria. Overnight Orvieto. Hotel, breakfast and dinner included.

Transfer to the Orvieto train station for connections throughout Italy. Orvieto is on the main north-south train line, so offers direct trains to Rome, Florence, Bologna and Milan.  Hotel and breakfast included.

The biking in Umbria can be quite hilly, with some longer “flattish” stretches. We ride 40 – 65 km a day, with optional extensions as well as van support, which allows you to relax off the bike for a while. We have designed the trip so that there is always some free time in the late afternoon so you can relax, read, or explore the towns where we stay. Breakfast is included every day, and dinners reflect the excellent traditional food of the region.