Bike Shed Grand Tour with Charley Boorman

Tour Plan

Day 1 (26/08)
‘Welcome to Rome’

Arrivals, bike pickup, briefing and dinner in Rome

We meet in Rome, where every great Italian experience deserves to begin. After the airport pickup and hotel check-in, the pace becomes deliberately easy: aperitivo, introductions, a full welcome briefing, checking the bikes, and dinner together in the city. This is the evening where the group comes together.

Day 2 (27/08)
‘The Umbria Ridges’

Roman backroads climbing into the green Umbrian ridges, with the first night near Orvieto

We leave Rome on smaller roads, cutting north as the city slowly disappears behind us. The first riding day is not about rushing. It is about finding the rhythm of the group, feeling the bikes settle underneath us, and watching the landscape change. The road begins in the Roman countryside, then gradually climbs into the greener folds of Umbria. The traffic fades, the bends arrive, and the views open across wooded valleys, ridgelines and hilltop silhouettes. It is the kind of riding that makes the tour feel like it has truly begun without making the first day too heavy. By the afternoon we arrive near Orvieto, in the volcanic heart of Umbria. It is the perfect first overnight stop: peaceful, atmospheric, and far enough from Rome to feel that we have crossed into a different Italy.

Day 3 (28/08)
‘The Chianti Region’

From Umbria into Tuscany and to our Chianti base

Today we cross from Umbria into Tuscany, taking the scenic way towards Chianti. The distance is deliberately modest, giving us a relaxed day on the road and time to arrive properly. The scenery changes gradually: Umbrian green gives way to Tuscan softness, with vineyards, olive groves, cypress trees and pale stone farmhouses beginning to appear along the route. The roads here have a different rhythm. They flow rather than attack, rolling through a landscape that feels familiar even if you have never been there before. By the afternoon we reach our agriturismo in the Chianti region, our base for the central part of the tour. Bags come off the bikes, helmets stay down for a while, and the mood shifts. For the next three nights, we are not passing through Tuscany. We are staying in it.

Day 4 (29/08)
‘To The Towers and The Vines’

The classic Chianti loop — vineyards, hilltop towers, a great winery, and a tasting back at base.

Our first Chianti loop is a ride though the Tuscany people dream about, but unfolded in the All Routes Italy way: by beautiful roads, with the famous places used carefully and never as a checklist. We ride through vineyard country, rolling hills and medieval villages, following the curves that make this region so rewarding on a motorcycle. The landscape is classic, but the pleasure is in the details — a cypress lined lane, a sudden view, a perfect sequence of bends, a perfectly kept historical home hidden behind olive trees. Lunch is in San Gimignano, the Manhattan of Tuscany, where the towers still dominate the skyline and the stop feels properly earned by the ride. There is time to pause, look up, and enjoy one of the most distinctive towns in the region without letting the day become too busy. The route also leaves space for a visit to Antinori, one of the most impressive wineries of the region. It brings a different layer to the day: contemporary Italian wine culture set into a landscape shaped by centuries of vineyards, farms and stone. Then we return to the same agriturismo, where a wine tasting awaits us.

Day 5 (30/08)
‘The Hidden Tuscan Route’

The rougher, quieter side of Tuscany: forest roads and old stone villages, ridden as a loop

The second loop shows a different side of Tuscany. Less polished, less obvious, and in many ways more rewarding on a motorcycle. We ride east towards hill towns, forested roads and old stone villages where the landscape becomes more rugged and the riding more varied. Anghiari is one of the highlights, with its strong sense of history and position above the valley, but the day is not built around a single stop. It is built around the roads that connect them. Beautiful places like Raggiolo and Poppi give the route character, but the priority remains the riding: clean bends, quiet stretches, changing scenery and enough flexibility to follow the best roads on the day. By the time we return to the agriturismo, we will have spent two full days exploring Chianti and its surrounding hills from the same base. That slower rhythm is what makes this part of the 2027 tour different.

Day 6 (31/08)
‘Val d’Orcia To Saturnia’

South through the cinematic Val d'Orcia and the thermal springs at Saturnia

We leave Chianti and begin turning south through some of the most iconic roads in Tuscany. This is the landscape that has travelled around the world in photographs, films and postcards: rolling hills, cypress-lined ridges, pale farmhouses, wide valleys and long views that seem almost too perfect to be real. On the bike, it feels even better. The roads flow naturally through the land, rising and falling with the hills, giving us a day that is scenic, relaxed and deeply satisfying without needing to be long. We pass through Pienza, a small Renaissance jewel with huge views over the Val d’Orcia, where lunch gives us time to slow down and enjoy one of the most characterful towns in southern Tuscany. From there, we continue towards Bagno Vignoni for a lazy coffee overlooking the thermal water, one of those stops that feels completely timeless. In the afternoon the landscape becomes warmer, more volcanic and more open as we ride towards Saturnia. We arrive early on purpose: the riding is done, the boots come off, and the final reward begins. Thermal baths, spa time and a little hard-earned pampering at the hotel — a perfect way to close the last full day of the tour before the return to Rome.

Day 7 (01/09)
‘Return To The Eternal City’

Tuff-stone country, a last lunch by the lake, and the run back into Rome

The final riding day begins with one last taste of southern Tuscany. We leave Saturnia on small roads, passing through the atmospheric tuff-stone country that makes this corner so distinctive. The villages here seem carved from the same rock they stand on, rising from cliffs and ravines in a way that feels older, rougher and more mysterious than the Tuscany of vineyards and cypress trees. The roads are part of the pleasure: narrow at times, twisty, scenic and full of character. It is not a long day, but it still gives us proper riding before the route begins to soften towards lake country. There is time for a morning swim before we continue towards Lake Bracciano for lunch by the water — an easy, relaxed final stop before Rome starts to pull us back in. From there, the last stretch brings us back into Rome. The bikes are parked, the helmets come off, and the week shifts from riding to celebration. One final evening in the city — aperitivo, dinner, stories from the road, and the easy camaraderie that has been building since the first night.

Day 8 (02/09)
‘Fly Home’

Breakfast and farewells.
For those staying on, Rome is not a bad place to let the trip fade slowly.