Dozens of pros in the Euro peloton—and an obscene number of Michelin-starred chefs—call the Basque region home. On this eight-day trip, pedal along the snaking mountain roads of the western Pyrenees, past pine forests, remote villages, and cherry orchards, pumping up for Indurain-worthy climbs, like a five-mile ride up Monte Jaizkibel, the highest point on the Cantabrian coast, and a 13-mile haul up Col Bagargui—known locally as the "Col du Sinistre," or "Evil Mountain." Feed-zone snacks include nutty Ossau-Iraty cheese and gâteau Basque (sweet cake with cherries). At night, sip Armagnac in white-stucco villas and historic inns, including a tenth-century castle, and dine on regal fare like wood pigeon and txipirones (baby squid). For cross-training, there's the txikiteo (tapas crawl) in San Sebastian and surfing in Biarritz. OUTFITTER: Velo Classic Tours; veloclassic.com PRICE: $5,000 DIFFICULTY: Challenging WHEN TO GO: June