Ride through the heart of Italy from the Adriatic Sea to the Mediterranean coast in Tuscany on a thrilling cross-country bike tour.
Come and ride across Italy with us on this quintessential cross-country journey as we dip our toes in the Adriatic sea and traverse the enchanting regions of Le Marche, Umbria, Lazio, and Tuscany to the Mediterranean coast. You’ll cover an incredible 280 miles and climb over 24,000 feet. Along the way, you'll indulge in sumptuous cuisine, world-renowned wines, and see charming medieval towns. You'll ride across the rugged, misty Apennine mountain range, roll through vine-covered landscapes, and climb up to the towering tufa mesas of Umbria before you celebrate your journey's end on the stunning Orbetello peninsula in Tuscany with a sunset cocktail. This is truly the once-in-a-lifetime experience for lovers of all things Italian!
Trip Wows
Traverse the rugged, misty Apennine mountains, which form the spine of Italy
Ride over 280 miles (450 kilometers) and climb over 24,000 feet (7,300 meters) as you go from coast to coast in five incredible days
Wander the twisting alleyways of the medieval town of Gubbio, beautifully set on the lower slopes of Mount Ingino
Savour fresh green olives and the crisp, dry, white wines of Orvieto
Enjoy a spontaneous gelato and the allegria of Italians' renowned hospitality
Happy cyclists in a medieval town square
Ancient towns of Umbria
Riding through the narrow cobbled streets and medieval piazzas of ancient towns in the Umbria region makes for an unforgettable Italian journey.
What Guests are Saying
I wanted a challenging ride and an opportunity to experience some Italian culture. It happened well beyond my expectations.
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I’m hooked! This felt extravagant but now I realize how important that extravagance was for having a great experience vs. a stressful experience. The guides made all the difference. I like the fact that there are different levels so we weren’t feeling held back or that we were holding up the group. The guides were all very professional about getting us to the finish each day still feeling confident about our rides…even if we were the last ones in.
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The food was fantastic. I thoroughly enjoyed getting to sample the local fare from each area.
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I saved for this trip for a long time, and I could not be more thankful for the guides and the experience. This was truly the trip of a lifetime and just the first in many more to come!!!!
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This was a great trip. I am glad I did it but it was tough. Because of your guidance, I think I was well prepared. Italy was the star—riding through intimate landscapes on relatively untraveled roads was delightful. Your preparation and staff made it even better.
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Truly an amazing and inspiring experience from start to finish. I would happily do this trip again.
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Great Ride
A century ride from Orvieto to the Orbetello Peninsula
What an epic day in the saddle! Achieve a great sense of fulfillment as you reach the Mediterranean Sea and toast with drinks on the beach!
Dates & Pricing
Book early for the best price
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Guaranteed
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Join Waitlist
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Private
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Limited Availability