Cycling Through Tuscany
Credit: David Epperson / Getty Images

In Tuscany, the most bike-crazed region of one of the world's most bike-crazed countries, two-wheeled tourists are treated like family. Those who pedal Tuscany's quiet back roads past Roman viaducts and through ancient walled villages are likely to get stopped by cars – not for a scolding, but for a prosciutto and mozzarella sandwich. Any Tuscany cycling trip should center around the region's most beautiful city, Siena, and should incorporate plenty of planned lunch breaks. (Ribollita, a hearty, fortifying bread soup, is a local specialty.) The classic route is a two-week loop on rolling roads past Siena's medieval ramparts and famous clock tower, heading south through the towns of Montalcino and Castelnuovo Berardenga, and ending in Montepulciano. In the lowlands olive presses, cheese-making shops, and vineyards are often open for tastings – and on steeper stretches, there's always wine at the top of the hill. The American outfitter Backroads offers a six-day tour along the rolling route.