Grand Tour Tuscany w Charley Boorman 2027

The Bike Shed Grand Tour with Charley Boorman returns in 2027 with a new route, a richer Tuscan heart, and the same ingredients that made the previous editions so special: brilliant roads, beautiful places, proper food, relaxed evenings, and the unmistakable atmosphere of riding through Italy with The Bike Shed community.

We start and finish in Rome, keeping the same easy arrival and departure format as the 2026 edition. But this year, once the city falls away behind us, the route opens into something different. We ride north through the green ridges of Umbria to our first countryside stop near Orvieto, before crossing into Tuscany and settling for three nights in a Chianti agriturismo.

That is one of the key changes for 2027. Instead of passing through Chianti, we stay. We unpack, slow down, and use the agriturismo as a base for two very different loop rides: one through the classic world of vineyards, towers and wine culture; the other into a quieter, more hidden Tuscany where the roads become wilder and the villages feel further from the usual trail. From there, the tour turns south again through warm Tuscan landscapes, before the final ride back to Rome by lakes, open countryside and one last lunch by the water.

With Charley leading the group, The Bike Shed bringing its unique energy, and All Routes Italy shaping the route, hotels, food and details behind the scenes, this is a Grand Tour built around the things that matter: great riding, memorable places, generous hospitality, and enough time to enjoy where we are rather than simply move through it.