Havana or San Jose, Costa Rica?

Havana has a real beach day close by. The Playas del Este, about half an hour east, are white sand with warm, clear water, full of Cuban families at weekends and calmer midweek. Facilities are simple, but a swim is easy to fit into a city stay.

San Jose cannot offer that. It sits high in the Central Valley, and Jaco or Puntarenas on the Pacific are two hours or more away by road, so the coast becomes a separate part of the trip and a hotel pool is the only swimming in town.

Neither city is worth travelling to for its cooking, and both rely on simple rice-and-beans plates: ropa vieja and roast pork in Havana, gallo pinto and the casado in San Jose. Where they differ is in where the pleasure lies. Havana's is in the glass, with daiquiris, mojitos and aged rum in old bars, and its best meals come from paladares in mansions and on rooftops, while state-run places disappoint.

San Jose is more reliable for everyday eating. Family sodas and the counters of the Mercado Central feed you well and cheaply, the local coffee is excellent, and Barrio Escalante adds modern restaurants and craft beer.

This is where Havana pulls well ahead. The colonial squares of Habana Vieja, the Morro and La Cabaña fortresses across the harbour and the art deco streets of Centro and Vedado make the whole city a sight. The Bellas Artes collection of Cuban art and the Museo de la Revolución add depth, and days of walking barely exhaust it.

San Jose lost most of its old buildings to earthquakes and rapid growth. The gilded Teatro Nacional, the Pre-Columbian Gold Museum, the Jade Museum and the National Museum in the bullet-marked Bellavista fortress are worth seeing, but they fill one or two days, not a whole trip.

Havana has the better night out, and it is built on dancing. There are rum bars in the old town, salsa clubs in Vedado and Miramar full of serious dancers, and on warm evenings the Malecón becomes an open-air meeting place. The scene is spread out and unpolished, but nights run late.

In San Jose, going out is smaller and mostly a weekend affair for locals: craft beer and cocktails in Barrio Escalante, student bars in San Pedro and the salsa bars of the El Pueblo courtyard. The downtown empties after dark, so you take taxis from door to door, and there is enough for a few good evenings.

Havana's outdoor life is mostly the Malecón, with waves breaking over the sea wall and sunsets over the Straits of Florida, plus the shade of the Almendares river park. Real landscape starts an hour west at Las Terrazas, and Viñales is around three hours away.

San Jose, ringed by volcanoes, is far better placed. At Poas and Irazu you can stand on the rim of an active crater, Braulio Carrillo drops from cloud forest to rainforest within an hour of the centre, and the Pacuare offers some of the best white-water rafting in the Americas.

Havana has only a few easy outings: Hemingway's Finca Vigía and Cojímar on the outskirts, Matanzas about an hour and a half east and the resorts of Varadero at two hours. Cuba's best places, such as Viñales and Trinidad, really need overnight stays.

San Jose has more to choose from close by. Cartago's basilica and church ruins, the old colonial church in the Orosi valley, the orchids at Lankester, the painted oxcarts of Sarchi and the coffee farm tours on Barva and Poas all make comfortable days out, though none of them is a destination in its own right.

Children are welcome in both cities, but Havana has less built for them. Its treats are the National Aquarium in Miramar, classic-car and carriage rides, the cannons at the fortresses and a beach day. Against that come broken pavements, heavy summer heat and shortages of baby supplies and medicines, so it suits older children better than toddlers.

San Jose comes out ahead because of what surrounds it: volcano craters you can drive to, waterfall gardens with sloths and hummingbirds, and butterfly farms, plus the Museo de los Ninos and La Sabana park in town. Families usually stay in the quieter western suburbs and get around by car.

Neither city has a metro or a bus network a visitor can easily use, so both depend on taxis. Havana has the edge because its core is walkable. Habana Vieja is compact, and you can walk along the Malecón to Centro and Vedado. For longer hops there are classic cars, shared almendrones and coco-taxis, with the fare agreed before you set off.

San Jose's downtown is small too, with a pedestrian stretch of Avenida Central, but heavy traffic clogs the valley at most hours and trips out of town take longer than they look. Taxis and ride-hailing cover the city, and anything further needs a hire car, a shuttle or a tour.

Neither city is a shopping destination, but they fall short in different ways. Havana is the one for things you can only take home from Cuba: a box of cigars, a bottle of aged rum, or a canvas bought straight from the painter in an old-town studio. San Jose has nothing as personal to offer, and beyond those few purchases Havana has little else to buy.

San Jose wins on everyday range. The Mercado Central is a working market where you can browse coffee and spices among the lunch counters, the craft stalls sell Boruca masks and oxcart miniatures, and when you need clothes or a forgotten charger the Escazu malls have them, which Havana does not. Neither city has a street worth strolling for style.

The two cost much the same, and in both you spend least by living as locals do. In Havana that means a room in a casa particular with a large breakfast, shared taxis and cheap live music. State hotels, paladares that price for foreigners and anything imported push the bill up, and you should carry cash, as card payments are unreliable.

In San Jose the savings are in soda lunches, buses and city hotels that cost less than those on the coast. Sit-down restaurants and alcohol cost close to North American levels, though, and park fees and tours charge foreign visitors more.

Music is a reason in itself to go to Havana. Son, salsa, bolero and rumba play live from midday in bars, courtyards and on street corners, and the jazz clubs of Vedado host some of the island's best players. The Gran Teatro is home to the Ballet Nacional de Cuba, and there is weekend rumba in the Callejón de Hamel and cabaret at the Tropicana as well.

San Jose's formal performance centres on the Teatro Nacional and its symphony orchestra, with dance and folk shows at the Melico Salazar and salsa bands in the dance halls. That fills an evening or two well, but it is not a scene to plan a trip around.

Rest in Havana comes from the pace of the city itself, while San Jose's quieter places lie just beyond its edge. In Havana that means long afternoons in a rocking chair in a colonial courtyard and evenings watching the sea from the Malecón. Spas are few, and the noise, heat and fumes make a guesthouse in leafy Vedado or Miramar the calmer place to stay.

San Jose offers a little more real retreat. There are lodges among the coffee farms on the volcano slopes and in the hills above Escazu, where nights are cool and quiet, and the Orosi valley has simple thermal pools within a couple of hours. The city centre itself is no more restful than Havana's.