This 10-day guided road cycling tour crosses Italy from west to east, from the Tyrrhenian coast near Pisa all the way to the Adriatic. The route moves through three of the country’s most rewarding regions: Tuscany’s iconic rolling hills and world-famous wine country, the green valleys and hilltop towns of Umbria, and the unspoiled Marche. The Apennine stages in the middle of the trip are the highlight for serious riders, with long mountain climbs and sweeping descents. A support van follows every day, luggage is transferred between 4-star hotels, and great dining means nothing is left to chance.
You’ll be transferred from Pisa airport or train station to the hotel, where the team welcomes us, walks us through the week ahead, and gets our bikes set up and ready. The evening ends with a welcome dinner together, a proper introduction to the Italian food and company we’ll have for the next 10 days.
Accommodation: 4-star hotel
Meals: Dinner
We leave the Tyrrhenian coast behind and set off from Bibbona, riding through the famous vineyards of Bolgheri, home to the legendary Sassicaia wine. A climb takes us to Montecatini Val di Cecina, where a mountain ridge road opens up sweeping views before we pass through Larderello, a fascinating geothermal area that produces 12% of the world’s geothermal energy. Contrasting, surprising, and beautiful, the stage ends in the ancient Etruscan hilltop city of Volterra.
Accommodation: 4-star hotel
Meals: Breakfast, dinner
Cycling: 62 km (39 mi)
Elevation: +1,150 m (+3,770 ft)
After breakfast, we drop down from Volterra toward Colle Val d’Elsa and work our way through quiet backroads, rolling through old historic villages in a constant rhythm of ups and downs. Our destination is Siena, one of Italy’s great medieval cities. The evening gives us the chance to explore its historic center on foot: the magnificent Duomo, the iconic Piazza del Campo, and everything in between.
Accommodation: 4-star hotel
Meals: Breakfast, dinner
Cycling: 82 km (50 mi)
Elevation: +1,300 m (+4,250 ft)
Today takes us through some of the most iconic scenery in all of Italy, the rolling hills at the heart of Tuscany. We pedal past old farmhouses, rows of cypress trees, vineyards, and olive groves on a stage that’s never brutal but never flat either. We stop in the medieval town of Asciano for a light lunch before continuing to Montepulciano, an Etruscan hilltop town famed for its Vino Nobile wine, its historic buildings, and its suggestive medieval center.
Accommodation: 4-star hotel
Meals: Breakfast, dinner
Cycling: 89 km (55 mi)
Elevation: +1,450 m (+4,757 ft)
We cross into Umbria, known as the Green Heart of Italy, and the landscape immediately shifts to something softer and greener. It’s a long day but without any major climbs, passing the shores of Lake Trasimeno, the largest lake in central Italy, where we stop for lunch or a coffee. Assisi comes into view early, perched dramatically on its hilltop. One of Italy’s most important cultural and religious cities and the birthplace of Saint Francis, it rewards the effort. Dinner and a glass of Umbrian wine cap the day.
Accommodation: 4-star hotel
Meals: Breakfast, dinner
Cycling: 90 km (56 mi)
Elevation: +900 m (+2,952 ft)
Today we enter the Apennines, the long mountain spine that divides the Italian peninsula, and the cycling changes character entirely. Long climbs with a steady, manageable gradient replace the rolling hills, and the scenery grows wilder and more dramatic. It’s the kind of riding that demands focus and rewards it equally. We arrive in Norcia, a culturally rich mountain town at the foot of the Monti Sibillini, well inside the boundaries of the national park.
Accommodation: 4-star hotel
Meals: Breakfast, dinner
Cycling: 91 km (56 mi)
Elevation: +1,508 m (+4,947 ft)
This is the queen stage of the tour. We ride from the valley of Norcia up to the Piano Grande plateau, where the fairytale village of Castelluccio di Norcia sits at 1,452 m above sea level. In spring, the surrounding fields burst into a wildflower bloom that’s unlike anything else in Italy. After taking it all in, a long descent carries us down into the Marche region, La dolce regione as the locals call it, and into the university town of Camerino.
Accommodation: 4-star hotel
Meals: Breakfast, dinner
Cycling: 86 km (52 mi)
Elevation: +1,700 m (+5,577 ft)
We explore the Marche today, a region that doesn’t get the fame of Tuscany but matches it for beauty. The route takes us through the Regional Park of Gola Rossa e di Frasassi, a dramatic natural canyon carved between the mountains. We ride quiet backroads through small, unhurried villages before finishing at an agriturismo, where dinner is all about local organic produce and regional wine. A simpler, more grounded way to end the day.
Accommodation: Agriturismo
Meals: Breakfast, dinner
Cycling: 66 km (41 mi)
Elevation: +1,500 m (+4,921 ft)
The final ride is a triumphant one. We set off from the hills of the Marche and pedal east toward the Adriatic, its sparkling green water coming into view as we descend toward the coast. In eight days of riding, we’ve crossed three regions, climbed over the Apennines, and pedaled all the way from one sea to the other. The last kilometers feel earned. They are.
Accommodation: 4-star hotel
Meals: Breakfast, dinner
Cycling: 75 km (46 mi)
Elevation: +1,100 m (+3,608 ft)
After breakfast, we transfer to Ancona airport or train station, marking the end of our amazing Italian cycling adventure.
Meals: Breakfast
Included:
Add-ons:
Not included:
This Italy cycling vacation is designed for experienced road cyclists with solid fitness who are comfortable spending several hours a day in the saddle. Daily distances range from 62 to 91 km (39–56 mi), with significant elevation gain throughout: up to 1,700 m (5,577 ft) on the hardest Apennine mountain stages.
Sustained climbing is a central part of the experience, so comfort on long ascents is essential. If you ride regularly and are used to multi-day cycling tours, you’re good to go.
Want to see what else is there in the area? Discover more Italy bike tours here!
On this tour, you can rent an entry-level carbon frame road bike; a high-end road bike; and an e-bike.
If you’re interested in any of these options, please leave us a note at checkout or contact us before the tour starts.
Here’s a list of the equipment you need to bring:
Cycling gear:
Other:
Dress comfortably and for the weather in clothes you can move in. We suggest bringing clothing appropriate for the season. Layers are best and don’t wear jeans.
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Group sizes and pricing
A cycling vacation in Italy can be arranged for larger groups. Contact us to make arrangements.
Min. age requirements
If your group has participants under the age of 18, contact us prior to booking to make arrangements.
The price for this cycling vacation in Italy is based on twin-share rooms, but a single occupancy room can be arranged at an additional fee. You can add it to your booking at checkout.
The starting point of your cycling vacation in Italy is Pisa International Airport – Galileo Galilei (PSA). From there, the guides will transfer you to the hotel on Day 1.
We highly recommend that you cover all your bases with insurance. To make your booking and traveling experience as carefree as possible, you’ll be offered to simply insure your trip with Redpoint at checkout.
Redpoint—the official 57hours insurance partner—tailors protection packages for adventure travel, offering a comprehensive travel program, even in remote locations! Trip cancellation, natural disasters, pandemic coverage, medical evacuation, primary medical expenses—regardless of the travel interruption that may happen, Redpoint will have you covered.