Kingston or Santo Domingo?

Neither city is a beach destination in itself: Kingston faces a working harbour and Santo Domingo a rocky, surf-beaten Malecón. Santo Domingo has the better beach days, though. Boca Chica's reef-sheltered lagoon is calm and shallow at about 40 minutes away, and quieter Juan Dolio lies just beyond.

Kingston's best swimming means a boat out to the little sandbar of Lime Cay, which is lovely but small, while Hellshire is known more for its fried fish than its sand.

The two are broadly level, each strongest in its island home cooking rather than in variety. Kingston's food centres on smoke and spice: jerk from oil-drum grills, patties, ackee and saltfish, with Blue Mountain coffee grown in the hills above.

Santo Domingo cooks heartier and milder, with la bandera at lunch, mangú for breakfast and sancocho on Sundays. It also adds atmospheric courtyard dining in the old stone houses of the Colonial Zone.

Santo Domingo has much the richer set of sights. Its UNESCO-listed colonial quarter packs together a run of New World firsts, from the cathedral to Calle Las Damas, with the Alcázar de Colón and the monastery ruins all within a short walk.

Kingston's sights are about modern Jamaica rather than architecture: the Bob Marley Museum, Trench Town Culture Yard and the National Gallery's Jamaican art, with Port Royal's pirate history across the harbour. They are memorable, but more scattered and less grand.

Both cities go out late and loud, but the nights feel different. Kingston's signature is the weeknight dancehall street party, with huge sound systems in neighbourhood lanes running until dawn. It is unique, but best reached with someone who knows the scene.

Santo Domingo is easier for a visitor to dip into. The Colonial Zone's bars and plazas fill up at weekends, and nights end on merengue and bachata floors or at a colmadón with plastic chairs and loud speakers.

Here Kingston is far ahead. The Blue Mountains climb straight from the city to a 2,256m summit, with cloud forest, rivers, coffee farms, the cool trails of Holywell and birds found nowhere else, all reachable in a day with a driver.

Santo Domingo sits on a flat, hot plain. Its outdoors means the cave lagoons of Los Tres Ojos, the botanical garden and seafront walks, while Los Haitises or the Jarabacoa mountains need an overnight stay.

The day-trip options are about equally limited, but they point in different directions. From Kingston you can go west to old Spanish Town, cross to Port Royal, take the highway to the north coast or tour a mountain coffee estate.

From Santo Domingo trips run east along the coast, to the hilltop village of Altos de Chavón or to Bayahibe for boats to Saona island, so they lean more towards beach and boat days.

Santo Domingo is the more manageable choice with children. An aquarium, a zoo, the cave lagoons and the cannon-lined forts give a few days of outings, and Boca Chica's shallow lagoon is gentle for small swimmers.

Kingston offers less: Hope Zoo and Gardens, ice cream at Devon House and a boat to Lime Cay. Heat, traffic and missing pavements weigh on families in both cities, which is why both often pair with a coastal resort.

Santo Domingo is easier to get around, mainly because its historic core is compact and walkable, and a simple metro and cheap app taxis cover the rest.

Kingston has no walkable centre to speak of. Its museums, downtown, the mountains and Port Royal are far apart, there is no rail, and most visitors end up paying for taxis or a driver for the day.

Kingston offers less to browse, and its malls are plain and practical. What it does well is things to eat, drink and play: Blue Mountain coffee, aged rum, hot sauces and reggae vinyl from the downtown record shops, with Jamaican-made gifts in the courtyards of Devon House.

Santo Domingo gives shoppers more to do. Calle El Conde is a pleasant pedestrian street to wander, and the Mercado Modelo suits anyone who enjoys bargaining for crafts. Blue larimar, found only on this island, and amber with insects caught inside are distinctive things to take home. Neither city does much luxury or design shopping.

Santo Domingo is the noticeably cheaper city. Local meals, colmado drinks, guesthouses and app taxis all cost little, and only the boutique hotels and smart Piantini restaurants approach European prices.

In Kingston, street food and patties are good value, but hotels are priced for business travellers and transport is the hidden expense, so a comparable stay costs more.

Kingston has the deeper live-music life. It is the birthplace of ska, rocksteady, reggae and dub, with weekly sound-system sessions, the studios around Orange Street and concerts through Reggae Month, alongside the National Dance Theatre Company and the national pantomime.

Santo Domingo's music is mostly danced rather than watched. The Sunday son and merengue concert in the San Francisco ruins is a lovely ritual, and the Teatro Nacional hosts the symphony, but the formal season is modest.

Neither city is restful, but Kingston has more ways to unwind. Its trump card is the mountains, where small retreats offer cool air above the coffee terraces, and simple mineral pools at Rockfort and the old hot springs at Bath add a bathing tradition.

Santo Domingo has no equivalent. Relaxation there means a hotel spa on the Malecón, a shady colonial courtyard or an evening walk by the sea.