Cycling Italy coast to coast

€ 1550 (from) / Per person

Cycling Italy coast to coast

From the Adriatic to the Tyrrhenian Sea
You will begin at the sparkling beaches of the Adriatic Coast. From there you’ll enter in a breathtaking mountain landscape. Beyond lies the vine-covered hills of Tuscan wine country, where you can enjoy the charming medieval towns & taste the rich, diverse wines at beautiful vineyard estates. Continue to the medieval fortress overlooking the picturesque Lake Bolsena & onwards to the shores of the Mediterranean Sea.

Along the way you will also be able stop in the small towns to experience the best of Italian culture & cuisine: the Renaissance Palazzo Ducale of Urbino, the ancient Roman amphitheater of Spoleto, the churches of Assisi, the medieval streets of Pienza, the wineries of Montalcino & the magnificent piazza of Siena.

  • 12 Days
  • Age 15+
  • Coast to coast


  • Urbino
  • Città di Castello
  • Montalcino and Brunello
  • Pitigliano and the Etruscan Mysteries


Day 1 – Pesaro   

Day 2 – Urbino   

Day 3 – Sant’angelo   

Day 4 – Città di Castello   

Day 5 – Cortona   

Day 6 – Montalcino   

Day 7 – Siena   

Day 8 – Castelnuovo dell’Abate   

Day 9 – Sovana   

Day 10 – Sovana Loop   

Day 11 – Posto Santo Stefano 

How does it work

We transfer your luggage

Just leave it at the reception desk with your name tag & you will find it at your next accommodation.

We book your hotels

We will book double rooms with private bathrooms in 3- or 4-star hotels, boutique B&Bs, or agritourism estates. You will find the vouchers to each hotel in your welcome package.

We supply GPS files.

In order to be more eco-friendly, we will provide a GPX reader application with a user-friendly interface, allowing for easy and real-time navigation

We can provide bike rental and delivery with hybrid, road or e-bikes with an additional cost (200-300 euros)

Departure: Pesaro
Destination: Porto Santo Stefano
  • 11 nights (in 3/4 stars accommodation)
  • All breakfast (dinners on demand)
  • Emergency number 24/7
  • Gps files 
  • Luggage transfer
  • Dinners
  • Tips

Our rental bikes

Our bikes are equipped with plastic water bottle, rear pannier, lock, kit repair, spare tubes, GPS available on demand.

Tour Plan


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. Overnight at central Hotel sea front.


Distance 50 km (moderate)

Day 2: Ride to Montegridolfo

Riding on the undiscovered Marche hills! beautiful landscapes and villages are the highlights of the day. Overnight at Palazzo Viviani a nice country resort in Montegridolfo.


Distance 55 km (moderate to difficult)

Day 3: Ride to Urbino

Urbino is one of the hidden treasures of Italy. It's glorious Medieval and Renaissance history has left many masterpieces worth visiting. Overnight at Hotel Italia Overnight at Historical residence ( 3 stars sup) and, because this is truffle land, a gourmet special truffle dinner is available (not included).


Distance 55 km (moderate to difficult)

Day 4: Ride to S. Angelo in Vado (via Saccocorvaro)

After the Urbino visit, you’ll start on traffic-free roads, riding through the 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 splendor Overnight at Historical residence (3 stars sup) and, because this is truffle land, a gourmet special truffle dinner is available (not included).


Distance 60 km (difficult)

Day 5: Ride to Città di Castello

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


Distance 60 km (difficult)

Day 6: Ride to Cortona (via Santa Maria del Monte)

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.


Distance 78 km (difficult)

Day 7: Cortona - Bagno Vignoni

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 Monticchiello hamlet on the terrace of a little restaurant that enjoys an amazing view. Overnight at Osteria dell’Orcia.


Distance 55 km (moderate to difficult)

Day 8: Ride to Arcidosso Monte Amiata

A long climbing to the Amiata, the highest mountain on the south of Tuscany which was an old Vulcan, overnight and special Tuscan dinner at Residence Capenti in Arcidosso, managed by Vincenzo.


Distance 50 km (moderate)

Day 9: Ride from Arcidosso to Sovana

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.


Distance 75 km (moderate)

Day 10: Sovana loop - Etruscan land

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 archaeological park in Sovana with the most imposing 3000-year-old Etruscan tombs; Tour Pitigliano, a medieval town with the oldest Jewish ghetto in Italy, Soak in the hot pools of Saturnia hot spring and be back in Sovana with its Romanesque churches and a timeless atmosphere.


Distance 85 km (moderate)

Day 11: Sovana - Pitigliano - Porto Santo 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.


Day 12: End of our service

Transfer to Grosseto train station.

Photo Gallery