San Juan or Santo Domingo?

San Juan is a real beach city. Isla Verde has a long stretch of sand sheltered by a reef, Condado and Ocean Park run along in front of the hotels, and Escambrón's calm bay is a few minutes from the old town. The open stretches can be rough, so stick to the lifeguarded balnearios.

Santo Domingo's Malecón faces surf breaking on coral rock, and nobody swims there. Beach days mean the shallow lagoon at Boca Chica, crowded and loud at weekends, or the quieter sand of Juan Dolio a little further east. Both are a pleasant outing rather than part of daily life.

The two cuisines are close relatives, and you will find mofongo and fried pork in both. San Juan offers more ways to eat. There are the seaside kiosks of Piñones, the Santurce market square at La Placita, the weekend pork-roasting stalls up at Guavate, and chef-led kitchens in Santurce and Condado. Island-grown coffee is worth seeking out too.

Santo Domingo's strength is simple, cheap home cooking: la bandera at a comedor lunch, sancocho, and late-night chimi burgers from street carts. Piantini and Naco do have modern Creole cooking, but once you have tried the classics there is less left to explore than in San Juan.

Both cities have a walled colonial core on the UNESCO list that takes two or three days to see properly, but the character differs. San Juan's is defensive. The great forts of El Morro and San Cristóbal command the headland, and the blue-cobbled streets and pastel houses between them make a pleasant place to wander.

Santo Domingo's draw is being first. It has the oldest cathedral, hospital and paved street in the Americas, the Alcázar de Colón and the monastery ruins. It also has more museums beyond the old town, around the Plaza de la Cultura.

Both cities stay out very late, and the weekend is when things really get going. San Juan's best nights happen on the street. People drink in the open between the small bars of La Placita, and the clubs on Calle San Sebastián play salsa alongside reggaeton. Hotel lounges and casinos in Condado and Isla Verde are the more polished option.

In Santo Domingo, almost every night ends with merengue and bachata on a crowded floor. The classic local night out is the colmadón, a corner shop turned open-air bar. The Colonial Zone is easy to walk at night, but elsewhere you need a taxi, and late at night it is wiser not to walk.

San Juan has far more within reach. El Yunque's rainforest trails and waterfalls are under an hour away, there are night paddles on the glowing Laguna Grande, catamarans take you snorkelling off the cays, and the Piñones mangrove boardwalk is on the edge of the city.

Santo Domingo's outdoors amounts to the cave lagoons of Los Tres Ojos, the botanical garden, Parque Mirador Sur and a sunset walk on the Malecón. The mangroves of Los Haitises, the pine mountains around Jarabacoa and the whale waters of Samaná are further off, each a long day out or an overnight stay, so keen hikers rarely use the capital as a base.

San Juan has more variety for day trips. Ponce has a colonial plaza and a major art museum, a short ferry crosses to the rum distillery at Cataño, and Loíza is the place for bomba and Afro-Puerto Rican culture. Culebra and Vieques are better as overnight stays.

From Santo Domingo, trips mostly head east along the coast: Altos de Chavón above its river, and Bayahibe for boats to Saona. Most of what is sold in the city is a beach or boat day, so there are fewer towns to see.

San Juan is the easier city with children. Kites on the lawn at El Morro, safe swimming at Escambrón and Isla Verde, and the short paved trails at El Yunque all fit into a day. English, US-style pharmacies and resort pools make everyday logistics simple.

Santo Domingo actually has more built for children, with the National Aquarium and the National Zoo, and Boca Chica's lagoon suits toddlers. The constant heat, broken pavements and the need for a taxi everywhere make it harder going, though, which is why many families add a coastal resort.

Getting around is much the same in both. You walk the old town and take ride-hail taxis everywhere else, because the rail lines serve commuters rather than visitors. Old San Juan is hilly with uneven cobbles, and seeing the rest of the island usually means hiring a car or booking a tour.

The Colonial Zone in Santo Domingo is easier on the feet. Beyond it, guaguas and shared carros públicos are cheap but confusing, and intercity coaches make it practical to travel out of the city without driving.

San Juan has a slight edge thanks to range. Plaza Las Américas is one of the largest malls in the Caribbean, Ashford Avenue has a short run of designer boutiques, and the old town sells carved santos, vejigante masks and guayaberas.

Santo Domingo's souvenirs are hard to find anywhere else: larimar, amber with insects trapped inside, and faceless clay dolls. You can shop for them along Calle El Conde or bargain hard in the Mercado Modelo. Both cities sell good cigars and rum.

Santo Domingo is much cheaper. A comedor lunch, street snacks, colmado beer and app taxis cost little, and mid-range hotels are reasonably priced. Only the boutique hotels and smart restaurants of Piantini push the budget up.

San Juan costs about what a mainland US city does. Restaurant bills include tips and taxes, beachfront rooms are expensive in winter, and a hire car adds up quickly. Eating at the kiosks helps, but it remains the pricier trip.

San Juan offers more on stage. The Centro de Bellas Artes hosts the symphony and touring theatre, the long-running Casals Festival brings classical music, and big concerts fill the arenas in Hato Rey. Open bomba sessions also let visitors join the drumming and dancing.

Santo Domingo's best-loved performance is free. On Sunday evenings son and merengue are played among the San Francisco monastery ruins while couples dance. The Teatro Nacional's season is modest by comparison.

Neither city has its own spa tradition, and both are noisy, but San Juan makes it easier to unwind. The resort spas of Condado and Isla Verde, yoga near the beaches and a lazy day by the pool or on the sand are all close at hand.

In Santo Domingo, a hotel spa on the Malecón, a shaded colonial courtyard or the botanical garden gives a short break from the horns and music. Most people who want real rest leave for the coast.