Welcome to Hooked on Cycling holiday and our cycling holiday in Italy which takes you by bike from the Adriatic coast in the east to the Tuscan coastline in the west. This fabulous biking vacation takes you from Marche through the Umbrian hills and onto the Tuscan mountains before descending to the blue sea of the Tuscany coastline. This independent cycle tour (self-guided) has been graded level 3 as there are a number of climbs to navigate but daily distances are never too extreme. You will be rewarded with stunning views, UNESCO Heritage sites, medieval fortified villages, and of course fabulous Italian hospitality and wine.
Most days have a long and short option
It is a requirement of booking this tour with Hooked on Cycling that you have suitable travel insurance which covers you for the chosen activity and for emergency evacuation and hospital care.
Relax in the beautiful Roman town of Fano with its nice beach
Leave the wonderful views of the Adriatic Sea and enter the rolling hills. The magnificent medieval and renaissance town of Urbino awaits you full of architectural and artistic masterpieces. On your ride visit Fossombrone an ancient Roman town located in the Metauro valley. The ancient fortified medieval town is well worth spending time exploring and being just over half the distance ideal for a refreshment stop. Once in Urbino visit the Duke of Urbino Palace, one of the most important Renaissance buildings in Italy. It has been a UNESCO World Heritage site since 1998.
Today continue cycling with views of towns and countryside to the beautiful medieval town of S. Angelo in Vado. S.Angelo in Vado has again Roman origins and like many such towns long historical ties to the church of which there are seven to be seen. After some refreshments, you start the long climb to Bocca Trabaria pass at around 1050m but it is followed by a wonderful descent to the Upper Tiber Valley and finally into Sanselpolcro.
Optional loop day on the 10-night tour around Sansepolcro.
Today you have an epic ride across the pre-Apennines Mountains that separate the Upper Tiber Valley from the Chiana Valle. First, you leave Sansepolcro in a southerly direction which is mostly flat terrain before you head west and start climbing gently to 1000m. You will have great views as you descend to Cortona located just north of Lake Trasimeno and Chiana.
Today you have a choice of 4 different rides depending if you are staying in Montepulciano or Pienza. Now you are in Tuscany where your cycle ride today is to Montepulciano one of the most beautiful hilltop towns of Italy known since old times for its prestigious Vino Nobile wine. Maybe your chance to taste some wine. Pienza is a town in Tuscany, Italy. The central Piazza Pio II is framed by 15th-century buildings like the Pienza Cathedral and Piccolomini Palace. The latter was Pope Pius II’s summer residence.
Optional loop day on the 10-night tour around Montepulciano or Pienza.
A fantastic ride on the slopes of the ex-volcano Mt Amiata passing through olive groves, durum wheat fields to chestnut woods of Amiata. A must-stop today is Monticchiello located in the Val D’Orcia a UNESCO World Heritage Site for its natural beauty. Monticchiello is a tiny village not as well known, as its neighbours Montepulciano or Pienza but just as stunning to explore.
Today you will cycle the wonderful descent from the slopes of Mt Amiata to the remote Maremma, a rural area once the core of the Etruscan Territories. You can also soak in the hot springs of Saturnia. Pitigliano really is quite stunning, carved out of volcanic stone it sits above the stunning green landscapes. The town is also locally known as “Little Jerusalem” thanks to its position close to Rome, where escaping Jews could find refuge. Pitigliano, as early as the 14th century, became an important haven for the Jews, and their numbers grew so much that they built a Temple in 1598.
Today a more relaxing easy ride in the flatlands of Maremma to the scenic promontory of Mt Argentario in front of the Tyrrhenian Sea. Your tour is now complete, and you have cycled Italy coast to coast! Spend a relaxing afternoon on the beach or take a dip in the sea to bathe those tired legs!
Possible extension to 10 nights with loop rides Sansepolcro and Montepulciano/Pienza.
Fly to Ancona, Bologna Forli or Bologna International airports and transfer by train to Fano
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