Bike Shed Grand Tour 2026 with Charley Boorman
From a swim in Lake Bolsena to the mountains of Umbria, with Tuscany’s quiet back roads and very generous tables in between.
Three weeks since we got back, and we’re still going through the photos. This September’s Bike Shed Grand Tour brought us together with Charley Boorman for a week riding from Rome into Tuscany, through Umbria and back over the mountains. Plenty of time on the bikes, some exceptional food, and a group that got very comfortable around a dinner table together.
We gathered at our hotel in Rome, surrounded by green, with space for the bikes and a first aperitivo together. The following morning we headed north into Lazio’s lake country, and by lunchtime we were swimming in Lake Bolsena. Riding gear off, cool water, lunch by the lake. We were getting into the holiday part of this pretty quickly.
By evening we’d reached our agriturismo in the Maremma. Warm-coloured walls, the pool catching the last light, and dinner being prepared outside. We unpacked for three nights and made ourselves at home.
From there we rode out towards the coast, into the hills and through Chianti. Tuscany was dry and golden, with dark rows of cypresses and vineyards stretching away from the road. Coming through the woods, we could feel the air cool through our jackets before heading back into the sun.
The riding was so good. Smooth tarmac, bend after bend, barely any traffic. We passed castles, crossed little stone villages and kept finding another stretch worth getting excited about.
Tuscan lunches became a serious part of our days. Thick-cut bistecca alla fiorentina, charred on the outside and beautifully pink inside, platters passed along the table, bread dragged through the juices. At one lunch, the hills rolled away below our terrace in layers of vineyards, olive trees and distant farmhouses. We had quite a view to go with that T-bone.
There was still plenty of riding ahead, but we weren’t about to rush this.
In Montalcino we visited Padelletti, whose family winemaking history goes back to 1571. One of the latest generation came out to welcome us as we gathered around the tasting table in the garden.
Among the wines were the 2020 Riserva and the 2016 Brunello Riserva, the one rated 97 points by Decanter. Some very special bottles to share, in the company of the family behind them.
Back at our agriturismo, the earlier finishes gave us time for a swim before aperitivo. Then dinner beside the pool, still warm enough to sit outside, with everyone getting progressively louder as the evening went on. A full day riding together somehow left us with even more to talk about.
Leaving Tuscany, we stopped for coffee at Bagno Vignoni, where a great stone basin of thermal water fills the centre of the village. As we pushed into Umbria, the landscape grew steeper and more rugged. Wooded slopes closed around the road, stone villages clung to the hillsides, and we followed the valleys deeper into the mountains.
The ride back towards Rome took us up into open mountain country, with bare ridges above us and long curves unfolding ahead. After the vineyards and shaded Tuscan lanes, the scale of it all was something else.
By our final dinner we’d spent a week riding, swimming, eating and laughing together, and there was a lot to raise a glass to. A huge thank you to Charley and everyone who joined us and brought so much life to the trip.
Three weeks later, we’re back to work, but those roads and those noisy evenings are still very much with us.
Thanks for a brilliant Grand Tour, everyone.
Next year, you could be in the photos. We’re heading back out with Charley and the Bike Shed crew from 4 to 11 September 2027, with a fresh route through Italy and three nights in the heart of Chianti. Bookings are already coming in—we’d love to have you along.