Just southeast of Tuscany lies Umbria: Italy’s « green heart » is a wonderful mix of vineyards, olive groves and tiny Medieval villages perched upon the hillside.
#Soak up the medieval ambience and ancient traditions of charming hilltop town
#Taste the splendid wine Sagrantino of Montefalco
# Delight in hearty ribollita, panzanella, fresh pastas and delicious pastries
#Enjoy gracious luxury hotels with distinct regional flavor
Stunningly beautiful region waiting to be discovered. Cycle through rolling hills dotted with castles, fortresses and watchtowers harks you back to the mysticism and mysteries of the Dark Ages and visit the well-preserved medieval hill towns harboring splendid Renaissance art and Assisi, where the region’s rich history can be found at every turn.
Bike tour to Torgiano and Lungarotti Winery estate, explore Deruta the pottery town. Two days in Montefalco: wander through vineyards of sagrantino grapes and taste the outstanding Umbrian wines
We’ll meet you at charming Vannucci. After the fitting of bikes you’re free to explore this delightful hill town Città della Pieve is a town high up on a hill striking for its intense terracotta colour. At the highest point the fortress dominates with its five square towers, while the town centre is Piazza del Plebiscito.
Bike ride from Citta della Pieve to Torgiano via Deruta
Your first tour wind past cornflower fields and isolated farmhouses, then into a series of gently rolling hills studded with minuscule towns that you’ll want to stop and visit. Not-to-be-missed is Deruta the pottery town. Highlight is Torgiano with his Museum of Wine, and just outside of town is one of Italy’s most prestigious and modern wineries Lungarotti. For the visitor interested in food and wine, Torgiano is a veritable treasure trove.
Level: Easy to moderate.
Total Distance: 56km/ 35miles
Bike ride from Torgiano to Montefalco via Assisi, Spello, Bevagna
Today you begin with a nice downhill ride into the broad Upper Tiber Valley, followed by a short climb up to Assisi, hometown of Saint Francis, perched on an outcrop overlooking the valley, gleaming soft pink against the dark-green backdrop of wild Mount Subasio. You’ll want to explore the city’s revered and very beautiful churches, its romantic castle and impossibly narrow streets. Visit Saint Mary of the Angels, one of the largest Christian basilicas in Umbria
Then continue and visit Spello, the hamlet Bevagna and finally arrive to Montefalco, quintessential Umbrian delicacy: the medieval hilltown. Extremely tiny, it occupies a hilltop placed so strategically that majestic views are available at the end of every street.
Total distance: 60 km/37,5miles
Along the way, you breeze past a few isolated rural churches and through a couple of towns too small to even make it onto the map. The first big church is Madonna delle stelle after 7 km form departure. Today is very gentle hills and part of flat terrain. Highlight is the visit of Spoleto, within its wooded setting, is the loveliest of the Umbrian hill towns. Its urbane atmosphere is enhanced by its superb monuments and by the Festival dei due Mondi, Europe’s leading arts festival held in june and july. Come back in time for a wine tasting in Montefalco, the area is famous for the Sagrantino Wine.
Total distance: 52 km/32,5 miles
Bike ride from Montefalco to Todi via Giano dell’Umbria, Viepri, Castagnola
Back roads are the main roads today, as you wend your way over hill and dale, past the tail end of mountain streams, silent forests and wild mushroom stands. You’ll see fewer people today, hear fewer 20th-century sounds and see fewer modern sights than any other day. At the end of this unique excursion you’ll take the customary uphill incline leading into Todi, whose proximity is heralded by the wonderful Santa Maria della Consolazione, a magnificent Renaissance church set amidst shrubs and treetops on the outskirts of town. Todi still has almost all of its medieval walls, and its pristine charm has made it a favourite country home of wealthy Romans and artists, as well as a host of artisans who have enlivened its streets with their shops.
Total Distance: 40 km/25 miles.
Bike ride from Todi to Orvieto via Prodo Castle.
Yet another – perhaps the most glorious – church awaits you at the end of this day, your reward for mastering some pretty steep inclines. Along the way you’ll pass several ruined castles which provide a perfect backdrop for a picnic, perhaps based on local salamis, cheeses and breads purchased in the morning.
By late afternoon you’ll see Orvieto, looming ahead on its strange plateau, crowned by the cathedral of Santa Maria, considered by one and all to be among the very finest churches in all of Europe.
Total distance: 46 km/28,7 miles
Optional bike tour to this ghost town: striking position a top a plateau of friable volcanic tuff overlooking the Tiber valley.
Distance 44 km/27,5 miles. Arrivederci

Price
Cost: € 1790 per person in double occupancy
Single room supplement € 690
Solo Traveller Supplement price on request
Inclusions
Six nights in luxury four & five star hotels
Six breakfasts
All Baggage transfers
RideWithGPS App: tracks, route notes, off-line navigation
Trip notes: Sightseeing & meals suggestions
Maps with elevation gain
Delivery bike at Citta della Pieve hotel & bike fitting
Pick-up of bikes and gear in Orvieto
Keepsake Cicloposse water bottle
Sales taxes
Not Included
Bike Rental per entire tour
Hybrid bike € 190 | Road bike, E-Bike, Gravel € 260 | E-Gravel € 350
City Tax each village charges a tax per each day between € 0,70 to 3,00.
Hotel Vannucci is a charming boutique hotel in the heart of Città della Pieve, a beautiful hilltop town overlooking the Umbrian countryside. Elegant yet relaxed, with a peaceful private garden, it is a lovely place to settle in and begin your cycling journey.
We particularly like the combination of comfort and location: step outside and you can explore the historic center on foot, enjoy the little streets, cafés and restaurants, and start getting a feel for the slower rhythm of Umbria. A warm and welcoming introduction to the days of cycling ahead.
Borgobrufa is an elegant countryside resort set on a panoramic hill about 4 km from Torgiano, surrounded by vineyards, olive groves and the rolling Umbrian landscape. It is also a luxury bike-friendly hotel, with a warm welcome for cyclists and facilities that make arriving and staying with a bike easy and comfortable.
We particularly like it as a place to completely relax after the ride. Once you arrive, there is little reason to leave: the extensive spa and pools are a real treat for tired legs, while the 4 Sensi restaurant lets you enjoy Umbrian cuisine right at the resort. A beautiful combination of cycling, countryside, wellness and good food
Palazzo Bontadosi is a beautiful historic hotel set directly on the main square of Montefalco, right in the heart of one of Umbria’s great wine towns. Once the bikes are put away, everything is just outside the door – restaurants, wine bars and plenty of opportunities to discover the local food and the celebrated Sagrantino di Montefalco.
We particularly like the combination of history and comfort: the hotel occupies a 15th-century palazzo, while its intimate spa, complete with a heated pool, is tucked away in the medieval cellars below. A perfect place to relax after the ride and enjoy the food-and-wine atmosphere of Montefalco.
Hotel Fonte Cesia is set in a beautifully restored 17th-century palazzo in the historic heart of Todi, surrounded by the atmospheric streets and architecture of this wonderful Umbrian hill town.
What we particularly appreciate here is the warm, welcoming hospitality and the character of the historic building. Once the bikes are put away, you are perfectly placed to explore Todi on foot, enjoy its cafés and restaurants, and simply soak up the atmosphere of the town. A comfortable and very friendly place to end a day of cycling in Umbria.
Hotel Palazzo Piccolomini is a charming historic hotel set in the heart of Orvieto, housed in a beautifully restored palazzo once connected to the noble Piccolomini family. Its centuries of history can still be felt throughout the property, right down to the ancient rooms carved into the volcanic tuff beneath the building.
We particularly like its location: once the bikes are put away, Orvieto is yours to explore entirely on foot, from the magnificent Duomo to its lively streets, restaurants and wine bars. A comfortable and atmospheric base for enjoying one of Umbria’s most fascinating hill towns.
For guests looking for a more refined stay in Orvieto, we can propose Palazzo Petrvs, an elegant historic residence located in the heart of the old town, just a few steps from the magnificent Cathedral.
Set inside a beautifully restored palazzo, the hotel combines frescoes, original architectural details, and contemporary comfort. The restoration was carried out with great attention to local materials and colors, inspired by the warm tones and stonework of Orvieto and its Cathedral.
Luxury spa & Wine tour
Pienza | Montalcino | Scansano
Breath-taking seascape

Tour Reviews
Ciao from Canada Giuliana, Matilde and Panos,
We want to take a few minutes to thank you all so much for making our cycling trip to Umbria so memorable. We had a wonderful time and felt extremely well looked after throughout our trip. This included all the pre-trip communication and advice but especially the care and friendliness with which Matilde and Panos attended to us. Panos was a master at setting us all up on our bikes which made a big difference to our comfort and confidence on new bikes. He managed to accomplish this with patience and a smile on his face despite our somewhat high maintenance group of riders. He and Matilde also kept a close eye on us after we lost all credibility by getting ourselves lost on day two and disappeared into a series of farmers’ fields – all part of the great adventure!
The routes were exceptional, the scenery spectacular and the itinerary along the way was just what we were looking for – just the right balance of lovely villages, gelato, wineries and Churches!
So thank you again for providing such a great trip for all of us. We are already talking about returning to Italy next year – perhaps you have a trip to Sicily that might work for us??
We wish you all good health and hope you have a great summer.
Regards,
Stephen, Janet and the rest of the crew.
Thank you very much for making my bike trip in Tuscany so enjoyable. I may try to ride with you in Sardinia next year in late September and early October. You should be very proud of your business and yourselves for being such great ambassadors for your country.
Dear Giuliana- We had a wonderful time on the cycling trip. The maps and route descriptions were excellent and the length of cycling for each day was just right. The hotels were all lovely – central and charming. I think that the route from Todi to Orvieto was my favourite. We got such a great view from up high and it was mostly quiet country roads. Thanks for organizing such a wonderful trip. It was a pleasure. Regards,
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