Havana or San Juan?

You cannot swim in central Havana, where the Malecón meets the sea as a wall of rock and concrete. A swim means a taxi half an hour east to the Playas del Este, which have white sand and clear water, simple shade, food stalls and lively local weekends. It works best as a day off from the city.

San Juan has its beaches in town. Condado, Ocean Park and the reef-sheltered sweep of Isla Verde line the hotel districts, and Escambrón's calm bay near the old town suits children and snorkellers. Some open stretches have strong currents, so it pays to use the lifeguarded balnearios, and Luquillo's palm-backed crescent is the classic outing.

Havana's table is narrow. The paladares in old mansions and on rooftops serve good ropa vieja, pork and lobster, but state restaurants are dull, menus depend on what the kitchen can get, and there is little street food. Havana's strength is in the glass: daiquiris and mojitos in the old bars, aged rum and strong sweet coffee.

San Juan eats more widely and more casually. You can have mofongo and alcapurrias at the Piñones kiosks, a night around La Placita, and the roast-pork stalls of Guavate in the hills, while Santurce and Condado have chef-led restaurants. Rum is everywhere in both, and San Juan adds the piña colada and its own mountain-grown coffee.

Both cities have a Morro fortress guarding the harbour mouth, but Havana has much more behind its fort. Habana Vieja spreads across four great colonial squares, with baroque churches and arcaded mansions, and beyond it come the Capitolio, the art deco and mid-century streets of Centro and Vedado, the Plaza de la Revolución and two important museums. That is several days of looking, with the crumbling buildings as much a part of it as the restored ones.

Old San Juan is smaller and better kept: blue cobbles, pastel houses, El Morro and San Cristóbal, and the cathedral with Ponce de León's tomb, all walkable in a day. Outside the walls there is the island's art museum and the murals of Santurce, then mostly modern city.

San Juan has the denser night out. From Thursday to Saturday the crowd around La Placita drinks in the street between small bars, Calle San Sebastián mixes salsa and reggaeton on its dance floors, and Condado and Isla Verde add hotel lounges, casinos and proper clubs.

Havana's nights are built around dancing too, in the serious salsa clubs of Vedado and Miramar and in old town bars that serve rum late. Its most memorable evening is the free one, sitting on the Malecón with the city. The scene is spread out, so a night usually means taxis between neighbourhoods.

San Juan has real landscape close by. El Yunque's rainforest, with its tree ferns, waterfalls and lookout towers, is under an hour's drive, and near Fajardo you can kayak at night through bioluminescent water or sail out to snorkel the cays. Closer in, there are the Piñones mangroves and winter surf on the north coast.

Flat Havana offers the sea wall, sunsets over the Straits of Florida and the shade of the Almendares park. For forest trails and river pools you go to Las Terrazas, an hour west, and for Viñales' limestone valleys about three hours.

San Juan has more to fill a day out. Ponce, over the mountains, has a colonial plaza and a fine art museum, a short ferry crosses to the rum distillery at Cataño, and Loíza is the home of bomba. Culebra and Vieques deserve a night of their own.

From Havana the easy outings are Hemingway's Finca Vigía, Cojímar and Matanzas, with Varadero's resort strip further east. Cuba's real prizes, Trinidad, Cienfuegos and Viñales, are too far for a day, and with poor public transport you need a car with driver or a tour.

San Juan is the easier city with children. English is widely spoken, and pharmacies, supermarkets and resort pools work as they do in the US. The calm water at Escambrón and Luquillo, the tunnels of El Morro with kites flying on the lawn outside, and the short paved trails in El Yunque make simple days out. The main things to plan around are the midday heat and the steep cobbles.

Havana welcomes children warmly and has the aquarium in Miramar, classic-car rides and cannons on the fortresses. Broken pavements, heavy summer heat and gaps in supplies such as baby goods and medicines make it better suited to older children who are curious about music and history.

In both cities you walk the old town and take taxis for everything else, and neither has public transport a visitor can rely on. In Havana the taxis are part of the experience: classic American cars, shared almendrones on fixed routes and coco-taxis, with the fare agreed before you set off. A walk along the Malecón links the old town to Vedado in under an hour.

San Juan runs on ride-hailing. Its single rail line misses both the old town and the beaches, and a hire car is the usual way out to El Yunque or Ponce, with heavy traffic on the highways at rush hour. Watch your footing in both places: on the hilly cobbles in San Juan, and on the broken, poorly lit pavements in Havana.

Neither is a shopping destination, but San Juan gives you more choice. Plaza Las Américas is one of the Caribbean's biggest malls, Ashford Avenue has designer boutiques, and the old town sells carved santos, vejigante masks, cigars and local coffee among the shops aimed at cruise passengers.

Havana has no fashion or department stores, and its shop shelves can be sparse. What it does offer is worth buying: cigars, aged rum and, above all, paintings and prints from the artists' studios in Habana Vieja and Vedado, plus the craft market by the harbour.

Havana is cheaper, if you travel its way. Casas particulares are good value and come with a big breakfast, and live music, museums and shared taxis cost little. State hotels, the smarter paladares and anything imported are expensive, though, and you need to carry cash because cards are unreliable.

San Juan costs about what a mid-sized city on the US mainland does, with tips and taxes added to restaurant bills and high winter rates at the beach hotels. Kiosk meals and the forts' small fee help, but car hire adds up. Summer rooms are cheaper because it is hurricane season.

Music is the main reason many people go to Havana, and it is the stronger of the two here. Son, bolero, salsa and rumba play from midday in bars, courtyards and on street corners, at a high standard everywhere. Vedado's jazz clubs and the Jazz Plaza festival add more, and the Gran Teatro is home to the Ballet Nacional de Cuba, with Callejón de Hamel and the Tropicana for the popular side.

San Juan's live music is more of a dance-floor affair, with salsa bands in Santurce and the old town. It also has bomba, where open sessions invite visitors to join in. The Centro de Bellas Artes, the Casals Festival and big reggaeton concerts in Hato Rey cover the rest.

San Juan makes rest easier to arrange. The resort hotels in Condado and Isla Verde have spas, pools and beach loungers, and yoga and massage are easy to find, though the streets outside are loud and real quiet means going out to the countryside or the small islands.

Havana has hardly any spas and no bathing culture. Its kind of rest is slowness: a rocking chair in a colonial courtyard or an evening by the sea. Traffic fumes and noise mean you sleep better in a guesthouse in leafy Vedado or Miramar.