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Tuscany Bike Tours

Exploring Tuscany & Umbria by bike

Italy’s central regions of Tuscany and Umbria have some of the most stunning scenery for you to explore on your cycling holiday. The serene and beautiful rolling green hills, vineyards, olive groves and sun-baked stone villages make this one of our clients' favourite Italian cycling destinations. Pedal along Tuscany’s Via Flaminia – once a Roman road over the Apennine mountains to Rome – visit the vineyards of Chianti and stop for a picnic by Lake Trasimeno. 

Cycle to charming medieval villages and hilltop towns in the countryside. San Quirico d’Orcia is a walled village in southern Tuscany with Etruscan origins, the 13th-century San Gimignano and Montepulciano are pretty towns made from sun-baked Tuscan stone on the hillside. E-bikes are available on Cycling for Softies tours to help you on the inclines, so you can save your energy for wine tastings and sightseeing.

The Tuscan and Umbrian cuisine does not disappoint, taste homemade parpadelle, pecorino cheese and fresh vegetables, paired with a glass of Chianti wine. Don't miss the Italian gelato for dessert; after a morning of cycling and sightseeing you will have earnt it.

Insiders tips:

  • Visit the Etruscan hilltop town of Cortona
  • Cycle along the famed Via Flaminia
  • Experience Italian hospitality at an agriturismo
  • Glide up the beautiful hills on an e-bike
  • Learn how to make home-made pasta

Italian cuisine and wine

Tuscany and Umbria produce rich olive oil, which is doused on salads, vegetables and meats. After cycling the surrounding hills, dine on Florentine T-bone steak, Umbrian trout, wild boar, cured meats and dishes made with Norcia black truffles, accompanied with vegetables.


Produced in central Tuscany, medium-to-full-bodied red Chianti wine has been produced for over 2,000 years, since Etruscan times. Montepulciano is a rich, medium-bodied red wine that complements pork dishes and red meat. Brunello di Montalcino wine has notes of cherry and plum and pairs well with cold cuts.

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Historical sights

Pedal around the charming towns dotted through the Tuscan and Umbrian countryside. Assisi was the birthplace of Latin poet Propertius and St Francis, who founded the Franciscan religious order. Cortona is enclosed with stone walls atop a hill, offering sublime views of the countryside and Lake Trasimeno.


Take a break from cycling and visit the ancient castles and fortresses in the Niccone Valley, the Romanesque Abbey of Sant’antimo and medieval towns of Montone and Gubbio, which is on Mount Ingino and has views of the Apennine mountains.

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