Cascais or Ronda?

This is the starkest difference between the two. In Cascais the beach is part of daily life: Conceição, Duquesa and Rainha lie under the old centre, the promenade runs on to Estoril, and Carcavelos is a few stops up the line for surf. The water is cool Atlantic, and wild Guincho is for watching rather than swimming, but a swim is never more than a short walk away.

Ronda has no sea of its own. The Costa del Sol is roughly 50km away over hairpin roads, warmer but built up, and the trip uses up a whole day. Most visitors settle for a hotel or farmhouse pool instead.

Cascais eats better, mainly because of the sea and the capital next door. Grilled sardines and bream, clams and seafood platters come from a working harbour, the Mercado da Vila is worth a morning, and long lunches on the Guincho coast are a local habit. When the town's own range runs thin, Lisbon is close enough for dinner.

Ronda offers sturdy mountain cooking instead: oxtail stew, lamb and game, hams from the Serranía and chestnuts and mushrooms in autumn, with local wines from the Sierras de Málaga. The good eating is in the Mercadillo tapas bars rather than the gorge-view terraces, and a few days exhaust it.

Ronda has the stronger sights by some distance. Its town is split by the Tajo gorge and joined by the eighteenth-century Puente Nuevo, and around it stand the Real Maestranza bullring, the Arab baths, the Mondragón palace and the rock-cut stairway of the Casa del Rey Moro.

Cascais has charm rather than monuments: the aristocratic villas of a former royal summer resort, the Citadel, and the Paula Rego museum in its red towers. It makes a pleasant day's walk, but for major heritage visitors go to Lisbon or Sintra.

Neither is a place for clubbing, but Cascais has a little more to offer after dinner. The old centre's narrow streets have pubs, wine bars and cocktail terraces that fill on summer nights, Estoril's casino adds a dressier evening, and Lisbon's nightlife is a train ride away if you plan for the last trains home.

In Ronda the evening is the late dinner itself, with tapas around the Plaza del Socorro and only a few bars afterwards. The town goes quiet early except during the September fair.

Both are excellent for time outdoors, and the difference is ocean against mountain. Cascais looks to the Atlantic: the cycle path to Guincho, the Boca do Inferno arch, cliff walks at Cabo da Roca, wind and waves for kitesurfing and surfing, and misty cork oak trails in the Serra de Sintra.

Ronda is ringed by limestone sierras. Grazalema has crags, the Garganta Verde and griffon vultures, Sierra de las Nieves has its Spanish fir forests, the gorge cliffs draw climbers, and the Caminito del Rey is an hour away. It is the choice for serious hiking, while Cascais suits watersports and coastal walks.

Cascais has the easier and grander set of outings. Lisbon and Belém are a short train ride along the shore, Sintra's palaces are just over the ridge, and Mafra, Ericeira and Óbidos are comfortable drives, so a week fills itself even without a car.

Ronda's outings are rewarding but more spread out. Setenil, Grazalema and Zahara are close, along with the Pileta cave and the Acinipo ruins, but the white villages really need a hire car, and Seville, Málaga or Gibraltar make long days on the road.

Cascais is far more comfortable with young children. Its shallow, sheltered coves, the flat promenade for scooters and pushchairs and the peacocks in the Marechal Carmona park make easy days, and Lisbon's Oceanarium and zoo are a train ride away.

Ronda welcomes children in its squares late into the evening, and older ones enjoy the bridge and the gorge walk. But steep cobbled lanes, exposed viewpoints and no sea make it harder work, and families tend to stay in a country house with a pool.

Both centres are walkable, but Cascais connects better beyond them. The coastal train runs straight to Lisbon, buses go to Sintra and Guincho, and a cycle path heads west, so many visitors never need a car.

Ronda is easy on foot apart from its steep lanes down into La Ciudad, but the trains and buses are slow and infrequent. For the villages and natural parks a car is close to essential, and parking in the old town is tight.

Neither is a shopping destination, but Cascais has more to browse. Its pedestrian streets mix surf brands, beachwear and small boutiques with tiles, cork and tinned fish, and Lisbon is close for anything serious. Ronda has Carrera Espinel's everyday shops and some souvenir ceramics and leather, and its best buys are the edible ones: local wine, cured meats and convent sweets.

Ronda is the cheaper stay. Tapas bars and set lunches are good value, the sights charge little, and rural houses in the hills are fairly priced, with costs rising mainly at the gorge-view hotels, at Easter and during the fair. A hire car is the main extra.

Cascais is an upmarket resort, priced high for Portugal, especially for seafront rooms in July and August. Back-street cafés, set lunches and the cheap train help, and coming outside high summer saves the most.

Both have only a little on stage, and Cascais has slightly more. There is the long-running Teatro Experimental in Estoril, casino shows, small concerts at the cultural centre and a summer jazz tradition, with Lisbon's opera and fado houses a train ride away. Ronda has mainly flamenco staged for visitors and an occasional municipal programme, and its big occasion is the Corrida Goyesca at the September fair.

Cascais has more for a restful break. Estoril grew up as a spa resort around its thermal springs, the big hotels have good spas and thalassotherapy, and seaside yoga and promenade walks set a gentle pace, though summer weekends bring crowds from Lisbon.

Ronda's Arab baths are a monument to visit, not to bathe in, and treatments are limited to a few hotel spas. What it does have is the quiet of a farmhouse in the hills, with a pool and olive groves.