Kingston or San Juan?

Kingston faces a working harbour, not the open sea, so swimming always means an outing. You can take a boat to the sandbar at Lime Cay, or drive to Hellshire, which is crowded and better known for its fried fish than its sand.

San Juan has proper city beaches along its Atlantic shore. Isla Verde has a long stretch of sand sheltered by a reef, and Escambrón is calm enough for small children and snorkelling. Luquillo is under an hour away when you want a classic palm-lined bay. Parts of the open coast have strong currents, so stick to the lifeguarded balnearios.

Both cities serve hearty island cooking with plenty of rum and mountain-grown coffee, and San Juan comes out a little ahead. Kingston's food is fiercely local: jerk from oil-drum grills, patties, ackee and saltfish, and curry goat at lunch counters. Beyond Jamaican cooking, though, the choice thins out quickly.

San Juan has its own staples, such as mofongo and roast pork, and seaside fritter kiosks at Piñones. On top of that, Santurce and Condado have chef-led restaurants, so a week of dinners has more variety. Weekend drives to the pork-roasting stalls of Guavate are a local ritual to match Kingston's Blue Mountain coffee.

San Juan has the stronger set of sights. Its walled old town of blue cobbles and colonial houses, guarded by El Morro and San Cristóbal, is a UNESCO site you can cover on foot in a day. The cathedral holds the tomb of Ponce de León.

Kingston's sights are about modern Jamaica rather than grand buildings. They include the Bob Marley Museum on Hope Road, the yard in Trench Town where he grew up, and the National Gallery's fine collection of Jamaican art. Port Royal's sunken pirate past adds some history, but much of downtown's Georgian architecture is worn.

In Kingston, a night out means a dancehall street party, with towering sound systems in neighbourhood lanes and dancers showing off new moves until dawn. In San Juan it means the crowd drinking in the street at La Placita. Kingston's version is the more singular experience, but it is hard to find without a local guide, and some of the best events take place in districts you should only visit with someone who knows the scene. Otherwise there are rum bars and lounges uptown.

San Juan gives you more nights out with less effort. La Placita fills from Thursday to Saturday, the bars around Calle San Sebastián switch between salsa and reggaeton, and Condado and Isla Verde add hotel lounges, casinos and clubs. You can find all of it on your own, though weeknights are much quieter than weekends.

Both cities have outstanding countryside close by, but it is very different. Kingston's is the Blue Mountains, rising steeply from the edge of the city to a 2,256m summit. Hikers climb through the night to watch the sunrise, past coffee terraces, cloud forest and birds found only in Jamaica.

San Juan's nature is wetter and closer to the sea. El Yunque's rainforest has waterfalls, and there are night kayak trips on the glowing bay near Fajardo, snorkelling around the offshore cays and winter surf on the north coast. In both cities, most outdoor days start with a drive.

San Juan has the slightly better choice of day trips. Ponce has a colonial plaza and a major art museum, and the drive takes you over the mountains. The rum distillery at Cataño is a short ferry ride across the bay, and Loíza is the place to hear bomba. Culebra and Vieques deserve a night or more.

From Kingston, Spanish Town and Port Royal are easy half days, and the coffee estates offer tastings. Ocho Rios and Port Antonio are within reach, but slow roads mean much of Jamaica is better seen with an overnight stay.

San Juan is by far the easier place to bring children. Kingston's one advantage is small: it has Hope Zoo, which San Juan lacks, with the lawns and shade of Hope Gardens next door. Add ice cream at Devon House and a boat out to Lime Cay, and that covers most of what Kingston offers families. A pushchair is no use on its roads, so the days are spent in the car between sights.

In San Juan the beach does most of the work. The sheltered stretches of Isla Verde and the calm, palm-backed bay at Luquillo make easy days in the water, and resort pools fill the gaps. English is widely spoken, and pharmacies and supermarkets work to familiar US standards, so the practical side needs little thought. The things to plan around are the midday heat and the steep cobbles of the old town, where a carrier works better than a pushchair.

You'll rely on taxis in both cities, but San Juan is easier to manage. Old San Juan can be explored entirely on foot, steep cobbles aside, and the beach districts are a short ride-hail away.

Kingston has no walkable centre to speak of. The museums, downtown, Port Royal and the mountains are spread far apart, the route taxis are confusing at first, and some districts are not safe to cross on foot. You'll need a hotel taxi or a hired driver for most days out.

San Juan has more choice. Plaza Las Américas is one of the Caribbean's largest malls, and Ashford Avenue has a short run of designer boutiques. The old town sells carved santos, vejigante masks and guayabera shirts alongside its cruise-passenger souvenirs.

Kingston's shopping is plainer, with simple uptown malls and almost no fashion. The best buys are things to eat, drink or play: Blue Mountain coffee, aged rum, jerk seasoning and reggae vinyl from the downtown record shops.

Neither city is cheap, but Kingston costs somewhat less. Street food is good value, though hotels are priced for business travellers, and paying for taxis, drivers and boats is the hidden expense.

San Juan charges US mainland prices in its tourist districts, with tips and taxes on top, and beachfront hotels cost the most in winter. In both cities, eating at kiosks and roadside stalls is the best way to save.

Both cities take music seriously, in different ways. Kingston is the birthplace of ska, reggae and dub. Sound-system sessions still run in its yards and hills, Orange Street keeps the memory of the golden-age labels, and the National Dance Theatre Company and the Jamaican pantomime give it a stage tradition of its own.

San Juan's music is salsa and bomba. Bomba has open sessions that visitors can join, and the Loíza festivals are its high point. For classical music it does better than Kingston, with the symphony orchestra at Bellas Artes and the long-running Casals Festival.

Kingston's way to unwind is a soak in spring water, while San Juan's is a resort spa by the sea. In Kingston the choices are the simple public pools at Rockfort Mineral Bath, the old hot springs at Bath, which are worth the long drive east, and quiet guesthouses in the cool mist of the Blue Mountains. Hotel spas uptown are the only pampering in the city itself, and the streets below are hot and loud.

San Juan makes a slow few days easier to arrange without leaving town. The large hotels in Condado and Isla Verde have spas, there is massage and yoga around the beach districts, and a lazy day by the pool or on the sand is never far away. The city gets noisy at weekends, and for real quiet you need the countryside or the small offshore islands.