Countries: Poland, Czech Republic & Austria
Distance: 250 miles
If you shrank the best of the Continent—stunning alpine valleys, historic sites and castles, local wines and cheeses—into the smallest space possible, it’d look a lot like the 250-mile stretch between Kraków and Vienna. The path connecting the two cities can be biked (painlessly) in five days, so take time when you arrive in Poland to explore medieval Kraków. Then rent some wheels from Art Bike and hit the road ($10 a day; art-bike.pl).
The path’s first 50 miles are bordered by a thick strip of apple orchards—a nice (and edible) perk. Towering rocks replace fruit trees near Mników, a valley studded with Jurassic fossils. Overnight in Oświęcim, next to one of the most unforgettably haunting sites in the world: the Auschwitz-Birkenau memorial (three-hour tour, $70; auschwitz.org.pl). Day two takes you across the Polish-Czech border, past ruined castles spiked with Gothic towers. Have a nightcap brew (or two) in the Czech college town of Olomouc and bed down at the comfy Hotel Gemo (doubles from $140; hotel-gemo.cz). Farther south, skip commercial Brno, but don’t miss a subterranean cruise through the Moravian Karst’s 1,100 caves ($7; moravskykras.net). Sleep at Penzion Kopecek, in Blansko (doubles from $50; kopecek.cz).
Fifty miles south, the low-rolling Palava Hills give way to the Czech Republic’s up-and-coming wine-growing region. (You’ll see plenty of Cabernet Sauvignons, but try Frankovka, a local red varietal.) Your last day on the trail, the language shifts from Czech to German as the path flattens out on its descent into Vienna. No one except for Czech border guards could get this close to the Austrian line during the 41 years of communist rule. Now you can cycle right through without even having to flash a passport.