Meet in Arezzo, a small Tuscan city steeped in Etruscan and Roman history • Find the rhythm of the region with a farm-to-table lunch at a countryside agriturismo • Pedal into the UNESCO World Heritage landscape of Val d’Orcia, a dreamscape of ancient olive groves and cypress-lined winding roads • Ride to Pienza, famed for its pecorino and ceramics • Continue to Montepulciano, a hilltop town of Renaissance palazzi and medieval passageways • Unwind in style at our serene resort hotel with its thermal pools and spa.  

Ride west through Brunello country, climbing to Montalcino’s fortress-topped hill and winding streets • Sample bold reds over lunch at a tucked-away countryside vineria • Pedal lesser-known roads with sweeping views and a final climb to Castiglion d’Orcia • Spin through the Crete Senesi, where chalky hills ripple beneath vast skies • Toast your adventures with a private dinner at a local winery • Close out the trip with one final push—ride along the slopes of Monte Amiata to Campiglia d’Orcia or hike to Vignoni Alto for panoramic views across the Val d’Orcia.