Lisbon or Valparaiso?

Neither city has a beach of its own, but Lisbon's are better for swimming and easier to choose between. The Cascais train passes the surf at Carcavelos and the calmer bays of Estoril, Costa da Caparica has miles of sand across the river, and the Arrabida coves have the clearest water. The Atlantic stays cool, but a swim is a real swim from June to September.

Valparaíso's waterfront is all docks and rocks, so beach days mean Viña del Mar, Reñaca or Concón. The sand is wide and sunny, but the Humboldt Current keeps the Pacific a few degrees colder than Lisbon's sea, and strong waves close some beaches, so most people sunbathe and take a quick dip.

Both cities eat from the sea, but Lisbon has much more depth. Family tascas, seafood beer halls, bacalhau cooked many ways, pastelarias on every corner and markets such as Campo de Ourique give plenty of choice, and good Alentejo and Douro wine is poured cheaply almost everywhere.

Valparaíso's cooking is plainer and more tied to the port: fried fish and conger eel soup at simple picadas, the morning catch at Caleta Portales and chorrillana to share over beer. The harbour-view restaurants on Cerro Alegre do more ambitious cooking with Casablanca whites, but the choice is narrow and quality is uneven.

Lisbon has the stronger sightseeing. The Manueline monuments of Belem, the rebuilt Baixa grid, the castle above Alfama, and museums such as the Gulbenkian and the National Tile Museum fill three or four days.

Valparaíso works the other way round. Its UNESCO-listed hills of painted iron-clad houses, funiculars and murals are the main attraction, and there are fewer collections to visit, with La Sebastiana the highlight. It suits wandering more than museum-going, and two or three days is enough.

Lisbon's nights are bigger and go on later. Crowds fill the lanes of Bairro Alto outside door-hatch bars, then move down to Cais do Sodre, and the riverside warehouse clubs at Santos and Alcantara run until morning. Principe Real adds quieter cocktail bars and the gay scene.

Valparaíso has a student and bohemian night that is lively for a city its size, from the wine bars on Cerro Concepción down to Subida Ecuador. It is rougher, though, and taxis between areas are wise late at night.

Lisbon puts more kinds of landscape within easy reach. The misty Sintra hills, the cliffs at Cabo da Roca, the kitesurfing beach at Guincho, the surf reserve at Ericeira and the limestone ridges of Arrabida, with dolphins in the Sado estuary nearby, each make an easy outing, and the Monsanto forest park gives shaded trails inside the city.

Valparaíso's outdoors is a rockier Pacific shore: cliff walks towards Laguna Verde and Quintay, the Concón dunes, sea lions in the bay and Humboldt penguins off Cachagua. For a proper hike you go to La Campana's palm forests and Darwin's summit, a longer trip inland, and in late summer the hills are dry and brown.

Lisbon has one of the best lists of day trips in Europe. Sintra's palaces are a short train ride away, and further out are walled Evora, the UNESCO monasteries of Alcobaca, Batalha and Tomar, and Obidos and Nazare.

Valparaíso's day trips are varied but less impressive. Viña del Mar is almost part of the city, Santiago gives a full day of museums, the Casablanca Valley wineries are close inland, and Neruda's house at Isla Negra sits on the rocks to the south. Few of them would justify a trip on their own.

Lisbon is far easier with children. The Oceanário's huge central tank, the science centre and cable car at the Parque das Nacoes, the zoo, and rides on trams and the Santa Justa lift give plenty to do, even though the hills are hard work with a pushchair.

Valparaíso's funiculars and harbour boats please children, but there is little else made for them. Broken pavements, traffic on narrow streets and street dogs make the city tiring, which is why many families stay in Viña del Mar and visit for the day.

Lisbon has far more ways to spare your legs. Its four metro lines, the trams, three funiculars, a street lift, suburban trains and river ferries all run on one card, though the metro misses Belem and the steepest old quarters, so some climbing is unavoidable.

Valparaíso has no metro or tram network up its cerros. The coastal train runs along the shore to Viña and trolleybuses work the flat lower town, but the hills rely on funiculars that do not always run, local buses and fixed-route colectivo taxis, and walking between neighbourhoods means long stairways.

Lisbon is the better place to shop. It ranges from the luxury boulevard of Avenida da Liberdade and the old shops of Chiado to designers in Principe Real and the LX Factory, and its crafts are worth bringing home: azulejos, cork, Burel wool and port.

Valparaíso's shopping is limited to galleries and studios on Cerros Alegre and Concepción, which are good for prints and lapis lazuli, and the weekend flea market near Plaza O'Higgins. For anything bigger, people go to Viña or Santiago.

Costs are broadly similar, but they fall in different places. In Lisbon, coffee, tasca lunches, wine and transport are cheap, while central rooms cost as much as elsewhere in southern Europe, especially in summer.

In Valparaíso the gap is between parts of the city. Hostels and guesthouses in the lower town and quieter hills are cheap, and set lunches, buses and funicular rides cost little. The boutique hotels and restaurants on Cerros Alegre and Concepción charge close to international prices.

Each city has a music of its own: fado in Lisbon and cueca porteña with boleros in Valparaíso's port bars. Lisbon's fado houses in Alfama and Mouraria are easier to find on any night.

Lisbon also has a fuller formal programme, with the Gulbenkian orchestra, opera at the Sao Carlos and the Centro Cultural de Belem. Valparaíso has the Teatro Municipal and the arts centre in the old prison, but for opera or a full classical season you have to go to Santiago.

Neither city has a bathing tradition, so a spa vacation belongs elsewhere. Lisbon still does rest better: hotel spas along the Estoril coast, shady gardens such as the Gulbenkian and Estrela, and quiet nights in the Sintra hills.

Valparaíso has only a few massage rooms in boutique hotels, plus the spas of Viña del Mar. Its restful moments are a terrace above the bay or a cliff-edge promenade watching the ships.