Twenty of the world's top athletes and explorers share their wildest dream trips—a dazzling list of never attempted feats daunting to even these world-class competitors. For the rest of us, consider their must-do adventures—and start planning. —Kate Siber

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Photo: A biker rides in the Medieval town of Maremma Roccalbegna
A biker rides in the medieval town of Roccalbegna in Tuscany, Italy.

Photograph by Martin Kirchner, laif/Redux

Kristin Armstrong

Road Cyclist

There are few things Italians love as much as food and wine, but bicycles are one of them. “Cycling in Italy is like football in America; everyone loves the sport,” says Kristin Armstrong, whose favorite Italian bike destination is Tuscany. “There is so much passion for bikes that while you are riding from town to town, or up the mountain passes, to and from the wineries, and even just down the road to get a nice cappuccino you can feel the passion.”

On narrow lanes, cyclists pedal through olive groves, lines of cypress trees, and crumbling farmhouses set in picturesque vineyards. In walled medieval towns, they indulge in a few of the Italians’ other passions—handmade cheeses, rich pasta dishes, and, naturally, plenty of vino. “The beauty of the country, the roads, the food, the people—you can’t beat it,” says Armstrong.

Outfitter Backroads offers guided six-day biking trips through Tuscany from $2,998.

Next: See Kristin Armstrong's Dream Trip: Bike the Highest Roads in Western Europe

See the Ultimate Adventure Bucket List 2011

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Photo: Cyclist Kristin Armstrong poses near her bike
Kristin Armstrong

Road Cyclist

Road cyclist Kristin Armstrong won the World Time Trial Championship in 2009 and a gold in the individual time trial event at the 2008 Beijing Olympic Games. She and cycling legend Greg LeMond are the only Americans to ever win three career medals at the UCI Road World Championships.