From the Tyrrhenian to the Adriatic, we cross Italy the way it deserves to be crossed: on a bike, through three of its finest regions, at a pace slow enough to actually taste the Vino Nobile in Montepulciano and fast enough to earn it. Ten days, nine dinners, one unforgettable Apennine crossing through the Monti Sibillini. We ride through Tuscany’s iconic rolling hills, Umbria’s green valleys, and the unspoiled Marche before the Adriatic finally comes into view. The finish line has never looked so good.
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.
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.
Deposits
Secure your spot either by paying in full or with a 50% deposit! The remaining 50% of the trip price must be paid 120 days prior to departure, at the latest. If booking within 120 days of departure, the full amount is required at the time of booking.
Cancellations
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Schedule a call with our adventure experts and let us help planning your dream adventure.
Luca was so helpful from the moment we booked, answering all our questions and helping us plan our trip. Our guide, Richi, and driver, Lorenzo, were fantastic. They took such good care of us and were always focused on the safety and comfort of the rider. We appreciated the small group size. The bikes (both regular and e-bikes) were top-notch. The scenery was, of course, spectacular. We enjoyed every day, our meals, and the accommodation immensely.