Italy Coast to Coast by Gravel Bike

We meet in the city of Ancona and transfer to Sirolo where we gather for a trip briefing and welcome dinner. Enjoy views over the Adriatic Sea and stroll Sirolo’s old town streets.

We head inland, cycling through Marche’s undulating hills and historic hinterlands on a mix of asphalt and gravel roads. We'll encounter the fortified medieval villages of Offagna and Polverigi and spend the night at a wine estate with excellent natural wines on offer.

We head for the eastern foothills of the Apennine Mountains via winding gravel roads. At first we pass through olive groves and vineyards before transitioning to the rugged valleys of the Gola di Frasassi. We spend the night in Italy’s 'City of Paper', Fabriano.

We cross the Apennines and cruise down to the town of Assisi, home to the UNESCO World Heritage site of the Basilica of St. Francis. From there we ride through the Umbrian countryside to reach our accommodation nestled in the green heart of Italy, famous for its olive oil.

Riding through Umbria’s wine region we reach Lake Trasimeno, Central Italy’s largest lake. From there, we follow an ancient canal into Tuscany and, surrounded by farms and vineyards as far as the eye can see, arrive in the picture-perfect hilltop town of Montepulciano.

Today we ride the famous chalky-white roads of Tuscany, twisting through Tuscan hills and vineyards for a challenging yet dreamy ride. We visit the Renaissance town of Pienza and the medieval village of Buonconvento. We spend the night in Montalcino, home of the renowned Brunello red wines.

We head south into the region of Maremma, a pristine and lesser-known region of southern Tuscan. Along the way we stop at the early medieval Abbey of Sant'Antimo and the beautifully restored Porrona castle Tonight we go glamping at a nature lodge nestled in the Maremma hills.

After a final climb to the town of Scansano, we descend steadily to the Tyrrhenian coast. Concluding the ride on the Argentario promontory – a rugged headland with stunning views over the sea – we gather for a farewell dinner in the evening.

Arrivederci! Extend your stay or travel onwards to your next destination.