Tuscany Trail

The Tuscany Trail began in 2014 as a trip among friends, Andrea Borchi's attempt to bring bikepacking culture to Italy, and 68 riders turned up for that first loop. It has since grown into what the organisers describe as the largest bikepacking gathering anywhere, with riders from around 70 countries, yet the founding rule has not changed: no standings, no clock, and reaching the finish is the only goal. More than half the field arrives for their first ever bikepacking event, so the mood is less about splits and more about who you end up sharing a table with in the evening.

The route is redrawn every year after long scouting of the region: white roads between vineyards, forest tracks, hilltop villages and historic centres, plus a few private stretches opened to riders only for this week. It starts on the Maremma coast, in wine country, and is designed for a gravel bike, though plenty of people ride it on a mountain bike. For 2027 there is an optional twist at the end: a ferry from Piombino to Elba, where the gravel runs past old mines, Mediterranean scrub and Napoleon's house of exile, with the sea at almost every bend.

It is self-supported in the true sense, with outside help ruled out, but you are rarely alone. Most riders sleep in hotels, B&Bs and farm stays along the way, while others pitch a tent at Base Camps run by the villages the route passes through, where dinner turns into swapping stories about the day. Mechanics with vans work along the route, and the team is out on the road photographing and filming as the field spreads across the region.