This ten-day tour is a true full immersion into two beautiful regions that are considered among the greatest places for bicycling vacations. You will see the very best of Central Tuscany and Umbria. These two regions are in themselves historically, culturally and climatically different.
Tuscany is known for its hamlets and hill towns, terracotta rooftops, swaying cypress and golden valleys, as well as being the birthplace of the Italian Language, the Renaissance, and the cradle of Italian art. It was a land of wars between hundreds of its towns and villages.
The holy Umbria was a land of peace historically bound to the Church State. It is the land of St. Francis and it is the “Green Heart” of Italy - with its green fields, plains, forests and meadows of the Apennine Mountains. It is known not only for its precious liquid, olive oil, but also for its white and pink Umbrian limestone that was used to build many of its medieval villages.
Day 1: BENVENUTI! Arrival at Montepulciano
Our Representative will meet you in Montepulciano and introduce you to the tour.
We have also prepared for you a self-led walk in the town and its environs.
Special Event of the Day: Visiting the town of Montepulciano and some of the local wineries.
Day 2: MONTEPULCIANO-MONTICCHIELLO-PIENZA-MONTEPULCIANO
Highlights of the Day: Views of Tuscan towns and countryside, and Pienza - the dream town of Pope Pius II, a place of architectural masterpieces where you can shop for ceramics and sample delectable Pecorino cheese.
Ride details: The level is moderate - 40 km (20% dirt, 80% asphalt) with rolling hills. A longer route (70 km) is also available.
Special Event of the Day: Visiting the town of Pienza.
Day 3: MONTEPULCIANO-CORTONA
Highlights of the Day: Views of Tuscan towns and countryside, and Montepulciano - one of the most beautiful hilltop towns of Italy.
Ride details: The level is moderate – 42 km (100% asphalt) featuring rolling hills with a big final climb to the town. A longer route (70 km) is available.
Special Event of the Day: Visiting the town of Cortona and cycling along the bike path on Trasimeno Lake.
Day 4: CORTONA-MONTONE/UMBERTIDE
Highlights of the Day: Views of the Chiana Valley and Lake Trasimeno from the slopes of the pre-Apennines Mountains, and the gorgeous gradual descent onto a minor asphalt road that will take you to the Upper Tiber Valley.
Ride details: The level is moderate to difficult - 55 km (1% dirt, 99% asphalt) with a long climb to pass, and an easy ride with another climb to the village of Montone. A longer route (75 km) is available.
Special Event of the Day: the fantastic descent and the medieval village of Montone.
Day 5: MONTONE/UMBERTIDE-ASSISI
Highlights of the Day: Today’s ride continues to follow the Tiber Valley, passing medieval castles and abbeys, on a road flanked by fields and forests to the slopes of Mt. Subasio where the fabulous Roman and Medieval town of Assisi lies, the home of St. Francis.
Ride details: The level is easy - 50 km (100% asphalt), mostly flat with some climbs and the final climb to Assisi. A longer route (70 km) is available.
Special Event of the Day: Visiting Assisi and the Lower and Upper Basilica.
Day 6: ASSISI-SPELLO-BEVAGNA
Highlights of the Day: Today, the core route is a short ride so you can stay longer in Assisi if you choose. The ride is along the Via degli Olivi, “Olive Grove Way”, and it will take you around the lower slopes of Mount Subasio. This road affords wonderful views over the plains below. The very picturesque town of Spello is the ideal location for a lunch stop on this route. From Spello, you’ll ride across the Umbra Vale to the foothills of the Montefalco territories, home of the superb Sagrantino red wine, to the Roman settlement of Bevagna.
Ride details: The level is easy - 40 km (70% dirt, 30% asphalt) with a short rolling section on the slopes of Mt. Subasio and then from Spello (10km) it will be pretty flat. A longer route (65 km) is also available.
Special Event of the Day: Wine tasting in Bevagna.
Day 7: BEVAGNA Loop
Highlights of the Day: Bevagna is a lovely small Roman medieval village. You may choose to relax in town or, for those who would like to cycle, there is a choice of wonderful rides to the wine areas, ceramics region and outstanding medieval hilltop towns.
Ride details: The level is easy to difficult (depending on the specific ride) and longer routes are available.
Special Event of the Day: From wine tastings to visits to your choice of Central Umbrian towns.
Day 8: BEVAGNA-SPOLETO
Highlights of the Day: Enjoy a gentle, easy ride on the Umbra Vale with scenic views of the hilltop towns that face it. A longer route will take you to Montefalco - a medieval town famous for its wines - and to Trevi, a gorgeous medieval town that is also known as the capital town of olive oil.
Ride details: The level is easy – 40 km (10% gravel, 90% asphalt) with rolling hills. A longer route (70 km) is available.
Special Event of the Day: The climb to Trevi and its descent, and a walk to the Towers’ Bridge (Ponte delle Torri) in Spoleto.
Day 9: SPOLETO Loop
Highlights of the Day: Spoleto is a wonderful roman medieval town with lots of things to see and places to go, our rides will be a short half day easy ride and a challenging and epic climb towards a remote area of Umbria.
Ride details: The level is easy to difficult (depending on the specific ride you choose) and longer routes are available.
Special Event of the Day: From wine tastings to a visit to Central Umbria.
Day 10: Ciao Ciao!
The tour ends after breakfast. Departure by train is available to reach Rome, Perugia or Firenze.