JIMENA DE LA FRONTERA , 20km further north of Castellar de la Frontera along the A369, is a far larger and more open hill town, rising to a grand Moorish castle with a triple-gateway entrance.
There are several bars , a beautiful old fonda ( which has no sign - ask for the Casa Maria , Calle Sevilla 36; under Euros12), the more expensive Hostal El Anon with restaurant and rooftop pool at Calle Consuelo 32, and another hostal at the train station, Los Arcos, a little way out of town. The best place for food is Restaurante-Bar Cuenca , Avenida de los Deportes, on the way into town, which does wonderful tapas and meals and has a pretty terrace patio at the rear.
Beyond Jimena, it's 23km further along the A369 - or on foot a 16km climb - through woods of cork oak and olive groves to reach GAUCÍN ; along the way there are bars at San Pablo, a hamlet about 7km out. Gaucín, almost a mountain village, commands tremendous views (to Gibraltar and the Moroccan coast on a very clear day), and makes a great place to stop over. Rooms and food are to be had at Hostal Moncada , Calle Luís Armiñian (tel 952 151 324; Euros18-27), next to the gasolinera as you enter the village from Jimena (get a room at the back for a view). Gaucín's charming fonda , the Nacional , Calle San Juan de Dios 8, closed its doors a few years back after 125 years in business, but is steeped in history and still serves meals .
You can reach the village by bus, but far more rewarding is the 13km, mostly uphill, walk from its train station . Though it's now known as Gaucín, this station is actually at El Colmenar, on the fringes of the Cortés nature reserve: if you need to rest up before the hike (getting on for 3hr) there's a hostal , Bar-Restaurante Flores (tel 952 153 026; Euros12-18) and several bars here. Should you chicken out, the hostal can arrange a taxi ride (about Euros12 one-way).
The train line between Gaucín and Ronda passes through a handful of tiny villages. En route, you can stop off at the station of Benaoján-Montejaque: from here it's an hour's trek to the prehistoric Cueva de la Pileta . From Benaoján, Ronda is just three stops (and thirty minutes) down the line.