Choose a cycling tour:

Tuscany and Umbria taylor made holidays since 1992

Cycling Italy coast to coast

The tour Coast to Coast, starts in Capo Conero near Ancona; it crosses the Appennino visiting the unspoiled Sibillini park. Along the way you will cycle by the most famous hill towns of Umbria and Tuscany fom Spoleto and Assisi to Pienza, Montalcino and Siena; Cycling further you will descends into the Etruscan Maremma to end on the Mediterranean shores near Capo Argentario. An incredible variety!


Activity Level: moderate to difficult / advanced bikers |  Mileage: 500-800 Km | Daily Cycling: 2 – 5 hr

Duration: 9 to 14 Nights

Distances: the tour feature up to 70 km on moderate terrain and 50 on mountain roads

Avalaible with hybrids/road bikes or personal bikes with a transfer of bike boxes to last hotel






Day 1 – Arrival in Pesaro

welcome service and bike fitting -Overnight at a charming country House outside the town. Pesaro is a small town by the sea. You can relax on the beach.



Day 2 – km 55 – moderate to diff

Urbino is one of the hidden treasures of Italy. Its glorious Medieval and Renaissance history has left many masterpieces worth visiting. Overnight at Hotel Italia or



Day 3 – km 40 diff – ride to S Angelo in Vado ( via Sassocorvaro –Piandimeleto)

After the Urbino visit you’ll start on traffic free roads, riding through an amazing scenery of soft hill the beauty of which has often inspired famous Renaissance painters such as Piero della Francesca! Reach St Angelo in Vado, of Roman origins, but whose present aspect testify of its Medieval splendour
Overnight at Historical residence ( 3 stars sup) and, because this is truffle land, a gourmet special truffle dinner is avalaible (not included).



Day 4 – km 60 diff. – ride to Citta di Castello ( via Apecchio e Bocca Seriola)

this is quite a tough ride crossing the Appenino mountains with spectacular winding roads and beautiful view over the Tiber valley. For those interested in Modern Art, the Buri museum is well worth visiting. Overnight at Borgo di Celle Country Inn (4 stars) not far from Citta di Castello – dinner included or at a charming, historical b&b in town.
Borgo Celle Country Inn or Antica Canonica.



Day 5 – km 60 level diff – ride to Cortona ( via S M del Monte e Portole) .

Today we have a great, though tough ride with beautiful views in a rugged landscape to reach Cortona that Frances Meyer book “Under the Tuscan sun” has made famous! Overnight at a central 4* hotel in Cortona.
Hotel San Michele



Day 6 – km 78 level difficult – Cortona to Montalcino

The soft hills covered by olive trees make a charming crown to the Trasimeno lake that can be seen while descending from Cortona. You are now in Tuscany heading for Montepulciano. It is wine country and you bike among vineyards. Lots of ups and downs first through a land of vineyards (Nobile di Montepulciano wine) then through the “Crete Senesi” then again among the Brunello vineyards. Take the time to stop either in Montepulciano or in Pienza; both towns deserve a visit. Stop for lunch in a tiny Monyticchiello hamlet on the terrace of a little restaurant that enjoys an amazing view. Overnight in a central hotel in Montalcino.



Day 7 – Ride ti Siena – – 50 km

Ride to Siena on a scenic road among the “Crete Toscane” ; Along the way you can stop to visit Monte Oliveto Maggiore imposing building with is superb cloister frescoed by Luca Signorelli. The ride is short enough that you have time to explore this famous cit. the duomo is very interesting and you should indulge an ice-cream at one of the cafés in Piazza del Campo, the famous square where the “Palio” is run. Night at hotel Chiusarelli.



Day 8 – 65 Km – Siena to St Antimo

Head back towards Montalcino on different roads and beyond it to reach St Antimo, a beautiful abbey in a serene setting. Along the way you can stop in Murlo, a charming hamlet of Etruscan origin. If the museum is open, it is worth visiting to get a better understanding of this mysterious civilization. Night in a nice b&b – il Borghetto (no web site)


For really strong bikers the loop can be done in one day (Montalcino Siena Montalcino)



Day 9 – Km 80 – Montalcino / Sovana

A rather difficult day, with some hard slopes around one of the most peculiar mountain in central Italy, Mt Amiata, the ancient volcano,. The first half is easier as it is a long slow descent among a sea of vineyards. Down from Montalcino to the peaceful St Antimo abbey The second part is the hardest as we get to the mountains area: cool chestnut woods and oaks groves makes this area pleasant even in the warm early summer days. We leave the mountains and start our way toward the sea. Leaving the mountains the landscape opens up and there are some nice views of the valleys. We reach Semproniano, a lovely hamlet on the top of a steep hill, then we descend toward Pitigliano, Sovana and Sorano, one of the most interesting Etruscan area. Of volcanic origin, the soft stone called “Tufo” could easily be carved both by wind and water, shaping a landscape of high perched cliff towns the Etruscan have also carved this soft stone into tombs, cellars and the amazing “Vie cave”(man carved canyons). We spend the night in Sovana. Sovana Resort



Day 10 – Km 75 – Etruscan land: Sovana loop

An almost unknown part of Tuscany: Sorano, Sovana and Pitigliano, the high perched so called “tufo towns”, made of soft rock that turns golden at sundown. The monumental, Etruscan tombs, the romanesque
Visit the archeological park in Sovana with the most imposing 3000 year old Etruscan tombs; Tour Pitigliano, a medieval town with the oldest Jewish getto in Italy, Soak in the hot pools of Saturnia hot spring and be back in Sovana with its Romanesque churches and a timeless atmosphere.



Day 11 – Km 85 – Sovana / Pitigliano / Porto S. Stefano

Last biking day of this trip. We enter Maremma a land that used to be a marshy hell ,( “My heart cries whenever you travel to Maremma fearing that you will not come back” says an old popular song). Now a day it is a fertile land, where cattle is grazing and wine is good, but still wild and unspoiled. At the end of the day you will be able to dip your toes in the salty Mediterranean. Spend the night in Porto S Stefano on the Argentario Peninsula. Hotel La Caletta.



Day 12 Transfer to Grosseto train station





At Viadelsole we are specialist in tailor made tours. Contact our team!

Share this tour: