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Anyone living in Sotogrande is likely to make excursions. It does not take long to discover old Andalusia. Minutes away from Sotogrande is San Roque. Although it cannot compare with some of the older towns on our itinerary, having been founded only in 1704, San Roque deserves credit for being a working inland hill town, unfazed by the smoky proximity of Algeciras or the looming Rock of Gibraltar. It's an ordinary-Joe sort of place, ignored by people dashing past on the way to Gibraltar, but it introduces you to the main themes of the remoter (but still accessible) historic towns further up into the hills.

Here you will find the steep narrow streets of white houses with their iron-grilled bay windows, the tiny squares and the profusion of flowers, date palms and orange and lemon trees that are characteristic of the region.

From here you can continue along the coast road, past Gibraltar, to the wonderfully Moorish town of Tarifa and the excellent if windy beaches along the coast of Cadiz, many of them magnets for serious windsurfers. That way also takes you, if you are a wine lover, to the fortress hill town of Vejer de la Frontera and the sherry towns of Jerez and Sanlucar.

But for the moment, turn inland instead and head up into the hills towards Jimena de la Frontera; the "de La Frontera" suffix to many town names round here stems from the time of the Christian fightback against the Moors when these hill fortresses were on the frontier between one culture and another. You pass through a country of cork and olive groves where huge storks' nests adorn telegraph poles and electricity pylons.

After a while, take the turning up to Castellar de la Frontera. Where the woods start to give way to rocks and prickly pears, high above a lake in the valley below, the moorish fortress suddenly materializes, an evocative and mysterious place.

Castellar's military high days, when Christians and Muslims fought over this strategic stronghold, ended in 1492. Since then, it has been a simple hill town with a rather dramatic presence from the outside and a marvelously unspoilt interior. Effectively, it is a cluster of houses, some amazingly tiny, crowded together within the old walls of the 13th century fortress and interwoven by flower-hung alleyway.

But only 20 years ago Castellar was virtually abandoned as people were decanted into a new town down below. After a phase as a hippy hangout, it has been gradually reclaimed by a mixture of its old population and a variety of expatriates from Britain and elsewhere in northern Europe.

On, then, to the other towns of the region, driving along twisting hill roads where one white town can nearly always just be seen from the next and where horses, mules and the long-horned Spanish cattle familiar from the bull-ring watch your progress. In the Arcadian woods below Castellar, the former Almoraima convent with its Moorish tower has become a Parador-type hotel. Jimena de Ia Frontera is a busy place, once people have emerged from their midday siestas. A fairly large town on its hill rising to an interesting Arab castle, it's a good place to find a café or restaurant, order some tapas or raciones and a chilled glass of Manzanilla sherry and watch the world go by. You'll need the refreshment because from here it's quite a climb to the next strategic stronghold, Gaucin.

Something of the vastness of Spain becomes apparent on this next leg of the trip. The countryside, good hunting territory for deer and wild boar, rolls on seemingly endlessly; traffic is normally very light and people and houses are very far between. But the trip is well worth it. Gaucin, built on a broken ridge to which cling astonishingly steep and narrow streets, commands remarkable views right across to Gibraltar and North Africa.

It is tempting to head straight off from here on the long march to Ronda, one of the most famous and romantically sited towns of the region. But instead, venture a little further off the beaten track, to Casares, a tiny little town that tends to get overlooked by the guidebooks. For me though, it is one of the highlights of the area, as good in its (very different) way as Castellar. If you're coming to it from the Gaucin direction, be prepared to subject your car suspension to the thumps and bumps of an often rough road.

In the old part of Casares, you will find not only houses built straight out of the rock, but rocky outcrops emerging unexpectedly straight out of the white walls of the houses, alongside the strings of tomatoes drying in the sun.

Take the alley up through an arch to the 16th century church on top (ruined since the Spanish Civil War). Up here is one of the most spectacular viewing points you'll find in this country of unexpected vistas. A stone wall marks the edge of the huge rock on which the town is built: something you might not be aware of until you lean over it and find yourself looking down, down, to the valley far below.

From Casares, take the winding road through the olive trees to the coast; a sprinkling of smart villas tell you that you are approaching a different kind of civilization. A few miles along the coast road and you're back in Sotogrande.