Experience must-see highlights including Pienza, a World Heritage site famous for pecorino cheese, exquisite ceramics and Renaissance architecture • After an abundant spread of Tuscan specialties, pedal cypress-lined roads through southern Tuscany's undulating terrain into the famed Val d'Orcia • Montepulciano, with its winding streets and hidden squares, invites a stroll • Unwind after the ride with a poolside lounge at our welcoming hotel.

Pedal an ascent through a sea of vineyards to the wine village of Montalcino, where enoteche pour samples and remarkable views reach as far as Siena on a clear day • Leave Val d'Orcia behind as you climb up the ridgeline to enter the lunar landscapes of the Crete Senesi, where we stop at an agriturismo with farm fresh Tuscan food • Our hotel's terrace provides an idyllic venue for a sunset aperitivo.

Bike along the exposed chalk hills of the Crete Senesi, often depicted in 14th- and 15th-century Florentine and Sienese paintings • Sun-drenched pastures dotted with sheep and crumbling stone farmhouses give way to oak woodland and olive groves • Take some time to explore Siena on your own • Ride rolling hills alongside Chianti Classico and Sangiovese vineyards • Get to know ridgetop Radda, the center of Chianti wine production • Looking for a gift? Family-owned Ceramiche Rampini offers ceramics hand-painted in the Renaissance tradition.