Stefan Brinkmann, from Tarifa Bike (011-34-956-681373, www.tarifabike.com), has an encyclopedic knowledge of the mountains of Sierra de Grazalema Natural Park, just north of town. He also has a permit that grants access to miles of backcountry singletrack, which weaves through classic Mediterranean cork-oak forests. Try the grueling 3.4-mile ascent of 3,609-foot Pico del Aljibe. Your reward will be a view clear to Morocco. Roadies can climb through the orange and olive groves to the ridgelines of Los Alcornocales Natural Park, then snack on tapasgazpacho, goat cheese, olives, paella, and fried calamariwhile riding from one ancient whitewashed village to the next. Cortijo El Aguilón (doubles from $180; 011-34-637-424-251, www.elaguilon.com), a cozy country inn tucked between the rolling hills just outside Tarifa, is a five-minute spin from the best of the backcountry singletrack. At day's end, its Turkish bath and spa will rejuvenate your weary quads.
If you need an energy infusionlocals are so laid back they often don't show up to kite until late afternoonbuy a ticket for the high-speed FRS ferry (one way, $44; www.frs.es) from one of the travel agents on Tarifa's main drag, then take the 35-minute ride across the Strait of Gibraltar to Tangier, Morocco. But don't stop there. Book a first-class berth on the ONCF ($31; www.oncf.ma), a train that will take you 11 hours south to the raucous markets of Marrakesh.