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Umbria–Tuscany itinerary by e-bike: climbs and wonders

E-bike cycling tour between Assisi, Lake Trasimeno, Val d'Orcia, Pienza, and Siena: a journey through hills, dirt roads, medieval villages, and the culinary excellence of Umbria and Tuscany.

A traveling ebike trip through Umbria and Tuscany that is not just a vacation, but a real experience to be enjoyed with your legs, heart, and mind. It starts in Assisi and cycle through green hills and scenic roads that look like they were designed. You will embrace Lake Trasimeno, and cross the village of Passignano sul Trasimeno, and climb towards breathtaking views that take your breath away and fill you with wonder. Then you enter Tuscany: vineyards, dirt roads, and a stretch of the historic Via Francigena, an ancient pilgrimage route that still today tells of centuries of journeys, encounters, and stories. The warm light of the Val d'Orcia accompanies you towards the Renaissance elegance of Pienza and the timeless charm of Siena. It is a challenging journey by e-bike, with challenging stages, climbs that make you feel the effort, and descents that make it all worthwhile. But that's where the magic happens: in the shared effort, in the toasts at the end of the day, in the kilometers that become memories.


Travel code
TOSEB
When are we leaving?
Based on the date
When are you coming back?
Based on the date
How long does it last?
5 days 4 nights
Per person
890 €

WHERE ARE WE GOING?

Program

First day

Individual arrival in Assisi, the green heart of Umbria and a city symbolizing spirituality and beauty. In the afternoon, welcome briefing: we get to know the group, the e-bikes, and our cycling itinerary cycling tour through Umbria and Tuscany. First dinner together to break the ice and start breathing in the atmosphere of the trip. Overnight stay in a hotel, ready to get on the saddle.

Second day

Between spirituality and vineyards: from Assisi to Trasimeno
We set off on our e-bikes with the right energy: we leave behind us behind us and dive into green hills, scenic roads, and silences that taste like summer. We climb towards Monte Civitelle amidst postcard views and fresh air. Along the way, for those who wish, there is a stop at a winery for wine tasting (optional, not included). Then Castel Rigone offers us a view of Lake Trasimeno and a descent that smells of freedom. Arrival in Passignano sul Trasimeno for dinner and a night in a hotel. This is Umbria in pure slow travel vibe. We will all meet up for dinner to spend the evening together.

Route information: 70 km and 1200 m elevation gain

Third day

From Umbria to Val d'Orcia: towards Pienza
Today we cross the border between Umbria and Tuscany, a true cycling tour through hills and historic villages. We cycle towards Montepulciano, home of Vino Nobile, through vineyards and scenic roads, then we pass by Chianciano Terme, famous for its thermal baths. The arrival in Pienza, a UNESCO jewel in the heart of the Val d'Orcia, is pure wonder: iconic views, Pecorino di Pienza cheese, and a Renaissance atmosphere. A sustainable travel experience by e-bike through nature, food, wine, and culture. After settling into our accommodation, dinner is free, and we are spoiled for choice!

Route information: 70 km and 1400 m elevation gain

Fourth day

Along the Via Francigena and arrival in Siena
We set off again from Pienza, cycling along the iconic white roads of the Val d'Orcia, among rolling hills and postcard views. We follow a stretch of the Via Francigena, passing medieval villages and ancient churches in the heart of authentic Tuscany. The entrance to Siena is pure excitement: the magic of Piazza del Campo welcomes us like an epic achievement. A cycling tour in Tuscany among history, nature, and iconic landscapes. After leaving our luggage at the hotel, all that remains is to choose a good trattoria for a typical dinner.

Route information: 80 km and 1200 m elevation gain

Fifth day

Last breakfast together, check-out, and a few more glances at the wonders we have experienced. Option to return to Assisi by van, crossing once again the hills and landscapes that have accompanied us on this e-bike trip through Umbria and Tuscany. Goodbyes, hugs, and that wonderful feeling of having shared the road, the effort, and the smiles. We return home with tired legs and full hearts.

  • accommodation in double rooms
  • return transfer of people and bikes from Siena to Assisi,
  • breakfasts and 2 dinners
  • cycling guide
  • health and baggage insurance
  • luggage transport from stage to stage
travel, entrance fees, tourist tax, drinks and extras, two dinners (in Pienza and Siena), any entrance fees to museums and monuments, and anything not specified under "Includes."
Single occupancy accommodation from €190.
Good to know
Where
accommodation
3- and 4-star hotels in Assisi, Passignano sul Trasimeno, Pienza, and Siena.
Tour guide
A member of the Jonas team who coordinates the group and accompanies them throughout the trip.
Itinerary information
This is a moderately challenging itinerant e-bike tour. The stages are consecutive and require good physical condition: you will be cycling for several days in a row, with long climbs and hilly sections. The e-bike helps manage the effort, but does not eliminate the challenge: you need to be used to cycling, able to stay in the saddle for several hours and willing to put yourself to the test. Recommended for those who already have experience in cycle touring or practice sports regularly. Not suitable for beginners.
Important
As with any active trip, the itinerary is subject to change—including the order of activities or stops—depending on weather conditions, road conditions, any temporary closures or restrictions at sites, locations, or areas to be visited, as well as the guide’s judgment, who will always act in the best interests of the group and the safety of the participants. The activity will take place even in case of bad weather, except in situations involving weather alerts or conditions that could compromise safety; we therefore recommend bringing appropriate gear for possible precipitation and temperature changes.
Train

Reference station: Assisi. From here, you can take a taxi or bus to reach the first hotel in Assisi.

Do you need more information?

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