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Coast to Coast

Can’t decide where you want to go? CyclinginItaly’s coast to coast tour is the perfect way to sample the nation’s many and varied landscapes and experiences. There’s something for everyone on this west-to-east adventure, so check it out!
jetty marina di pietrasanta Versilia Tuscany
aerial tuscany hills


Where better to start this premium cycling holiday than Lucca, Tuscany’s jewel, where we embark on our tour through olive groves, vineyards and lush hillscapes? We take on challenging ascents and descents to reach the Chianti area.

Moving on to Siena and Montalcino, we travel through Etruscan villages that time forgot, past hot springs to Cortona via a procession of medieval hilltop settlements in Umbria. The lovely town of Ancona on the Adriatic sea awaits for some rest and recreation.

719 km
8 days
7 nights
7 cycling days
10,270 m

Trail Highlights

Take in the sights and a unique five-star dinner in the world-famous town of Assisi, renowned for its beautiful architecture and the Basilica of San Francesco.

Journey into the hills to discover the hidden Chianti villages of Castel San Gimignano, Colle Val d’Elsa and Radda, then visit a local winery to sample the rich, ruby red wines of this fertile Tuscan region.

san gimignano tuscany
Tour and Stopovers

“I don’t ride a bike to add days to my life.
I ride a bike to add life to my days”

— unknown


Mouthwatering local and home-made dishes will tantalise your taste buds as you cross the Italian countryside.

Enjoy rich breakfasts, traditional lunches and chef-created five-star dinners as you refresh between rides. It’s an unforgettable culinary experience, topped up with the finest wines.

Useful Information

Look Forward to

The medieval Belforti Tower, surrounded by stunning hills and woodlands.

Hot springs bathing year-round in the tranquil natural haven of Fosso Bianco. .

The beautifully preserved medieval city of Orvieto, perched on high