Route: Ghisallo con Valbrona
Distance: 87.2 miles
When in Milan, see da Vinci's The Last Supper, eat risotto, and ride this legendary course. Biking from the city to Santuario della Madonna del Ghisallo belongs in the cycling canon of epic rides. Locals make the two-wheeled journey to pay homage to the patroness of cyclists (Madonna del Ghisallo) and visit the small mountaintop bike museum, but the whole route is like rolling on holy ground, with each turn offering a splendid new surprise. Years from now, you'll be able to recall it all: the 16th-century villas, ancient monasteries, abandoned medieval castles, sky-high villages framed by the Grigna Mountains, and the stunning hamlets tucked along Lake Como.