Chianti to San Gimignano Bike Tour

About this tour

Cycle through Chianti's wine country on a 30km intermediate-to-advanced route, passing vineyards and olive groves before reaching San Gimignano, the medieval town famous for its 14 towers. Over eight hours you'll navigate rolling Tuscan terrain with a support vehicle in tow, explore the UNESCO-listed hilltop settlement on foot, and finish with wine and olive oil tastings. Small groups of two to seven riders keep the pace manageable.

Highlights

• 30km ride through Chianti vineyards and olive groves
• Medieval San Gimignano with 14 iconic towers
• 45-minute walk around UNESCO world heritage site
• Wine and extra virgin olive oil tasting included
• Support van accompanies the group throughout
• Private tour with English-speaking guide
• 400m elevation gain across rolling Tuscan hills

What to expect

Expect a steady day in the saddle across variable terrain—mostly country lanes with some main-road sections. The route climbs 400 metres total, spread across the ride rather than in one punishing stretch. You'll stop frequently for photos and to catch your breath at viewpoints overlooking the Chianti landscape. Once you reach San Gimignano, ditch the bike and walk the medieval streets for 45 minutes, soaking up the compact town's architecture and atmosphere. The tour finishes at a local producer where you'll taste regional wines and olive oils. A support vehicle trails the group, so mechanical issues or tired legs aren't deal-breakers.

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