San Juan or Trinidad, Cuba?

San Juan has its beaches inside the city. Isla Verde has long sand sheltered by a reef, Condado and Ocean Park run in front of the hotels, and the calm bay at Escambrón is a short way from the old town. Luquillo is there for a classic day out. The catch is that some stretches have rough surf and strong currents, so swim at the balnearios with lifeguards.

Trinidad has one real beach, Playa Ancon, a taxi or bike ride from town, plus the smaller local shore at La Boca. The Caribbean there is calm and clear with snorkelling on the reef, but it is an afternoon away from the old town rather than a base for a beach trip.

Food is one of the clearest gaps between the two. San Juan has a full Puerto Rican cuisine to explore: mofongo and alcapurrias at the seaside kiosks of Piñones, the chef-led restaurants of Santurce and Condado, the market square of La Placita and the pork-roasting stalls of Guavate up in the hills.

In Trinidad the best meals are often at your own casa particular: rice and beans, roast pork or lobster, with a canchanchara in a clay cup. Menus repeat, supplies are uncertain and there is no street food, so eating is pleasant but not a reason to go.

Both are UNESCO-listed colonial towns you can cover in two or three days, but they feel different. Old San Juan is a walled fortress city. It has El Morro and San Cristóbal and the cathedral with Ponce de León's tomb, and out in Santurce there is a proper art museum and streets of murals.

Trinidad is quieter and more fully preserved. It is a sugar-era town of single-storey houses and red-tiled roofs around the Plaza Mayor, with small house museums and a view from a bell tower. You go there to wander rather than to tick off sights, and the UNESCO listing extends out into the sugar valley.

San Juan has far more to go out for. Crowds drink in the street at La Placita, Calle San Sebastián mixes dive bars with dance floors playing salsa and reggaeton, and Condado and Isla Verde add hotel lounges, casinos and clubs. Weekends are much busier than weeknights.

Trinidad's nights are warm and sociable but small. They centre on the steps by the Plaza Mayor, a few courtyard bars and a club inside a cave above town, and after a few evenings you have seen the pattern.

San Juan has the edge for a varied outdoor trip. El Yunque's rainforest is under an hour away, the glowing lagoon near Fajardo makes a good night kayak trip, the reefs of the offshore cays are good for a day of snorkelling, and the north coast has surf in winter.

Trinidad's mountains are closer and more rugged. Topes de Collantes has steep, humid trails down to waterfall pools, and horse rides cross the Valle de los Ingenios. With the reef off Ancon as well, it is a good base for hiking, best in the dry winter months.

Trinidad is better placed for days out. The Valle de los Ingenios begins at the edge of town, with its ruined sugar mills and the Manaca Iznaga tower. Cienfuegos, Sancti Spiritus and Santa Clara each fill a day with colonial streets or history, though you can only reach them by taxi, hired car or tour.

From San Juan the main town to visit is Ponce, over the mountains, while Cataño's rum distillery and Loíza's Afro-Puerto Rican culture are nearer. Culebra and Vieques are the real prize, but they need an overnight stay.

San Juan is the easier pick with children. The forts and the kite-flying lawn at El Morro, the calm water at Escambrón and Luquillo, and El Yunque's short paved trails fill several days. Resort pools, pharmacies and familiar US standards make the practical side easy.

Trinidad is friendly to children and the shallow water at Ancon makes a good day out. But pushchairs are useless on its cobbles, and power cuts and the shortage of familiar food and medicine make it hard work with small children.

Neither city has transport a visitor can rely on, but the problems differ. San Juan is spread out. Old San Juan is walkable and the beach districts are a taxi or ride-hail away, but the one rail line reaches neither, and seeing the rest of the island means a hire car on busy highways.

Trinidad is compact. You can walk the whole old town, and many lanes are closed to cars. Getting out is the hard part, with shuttles or bikes to Ancon and slow, infrequent coaches to other cities.

San Juan offers much more range. There is the huge Plaza Las Américas mall and the designer boutiques on Ashford Avenue, and Old San Juan sells santos, vejigante masks, guayaberas and local coffee to take home.

Trinidad's shopping is almost all handmade: embroidery and crochet along the craft market lanes, family pottery workshops and small galleries. It is worth an hour, but there is nothing else, and the same goods appear from stall to stall.

Trinidad goes much further on a modest budget. A room in a casa particular with breakfast costs little, the music in the squares is nearly free and you need no transport in the old town. Taxis, tours and paladar meals priced for visitors are what add up, and you need cash.

San Juan costs about the same as a city on the US mainland, with expensive beachfront rooms in winter and tips and taxes added to restaurant bills. Kiosks and the cheaper summer months help, but a hire car soon adds to the total.

Music matters in both cities, in different ways. San Juan has the broader scene. Salsa bands and open bomba sessions sit alongside the Centro de Bellas Artes, the Puerto Rico Symphony Orchestra, the Casals Festival and big reggaeton concerts in Hato Rey.

Trinidad has no formal stage. What it has is close at hand every evening: son, bolero and trova at the Casa de la Musica and the Casa de la Trova, and Afro-Cuban drumming at the Palenque de los Congos Reales.

Neither is a place for a wellness trip, but San Juan makes rest easier. There are resort spas in Condado and Isla Verde, yoga and massage near the beaches, and pools to lie beside, even if the streets beyond are loud.

Trinidad's calm comes from the slow pace of shaded courtyards and rocking chairs, broken by roosters, horse carts and late music, and the only massages are at a few hotels near Ancon. Power cuts that stop the fans make it harder to rest.