Montego Bay or Trinidad, Cuba?

Montego Bay has the better sea. You can walk from the Hip Strip onto Doctor's Cave Beach, the resorts east of town have their own sheltered sand, and the calm reef water is the backdrop to the whole stay. The town beaches are small, but a long beach day at Negril's Seven Mile Beach is within reach.

Trinidad's beach is a separate outing. Playa Ancon is a long, pale strip a short taxi or bike ride from town, with good snorkelling, and La Boca offers a smaller, local stretch of shore. It is a fine place to spend an afternoon between days in the old town, but the sea does not shape the trip the way it does in Montego Bay.

Montego Bay eats better and with more variety. Jerk smoked over pimento wood at roadside pits, patties from bakeries, ackee and saltfish, curry goat and fruit from street vendors give it a real street-food culture, even if fine dining barely goes beyond hotel dining rooms.

In Trinidad the best meals are often the home cooking served at your casa particular, along with lobster and roast pork in paladares on colonial rooftops. Shortages mean the same rice, beans and ropa vieja appear on menu after menu, and there is no street food to explore between meals.

Here Trinidad is in a different league. The whole old town is the sight: cobbled lanes, pastel houses with wooden grilles, the Plaza Mayor ringed by planters' mansions, and the San Francisco bell tower, all listed by UNESCO with the sugar valley beyond. The museums are small, but simply walking the streets fills two or three days.

Montego Bay's heritage fits into a morning or two. Rose Hall and Greenwood great houses, Sam Sharpe Square and the Georgian parish church are worth seeing, but the centre is a commercial district, and serious history lovers end up in Falmouth.

Both scenes are small, but they feel very different. Montego Bay's evenings centre on the open-air bars of the Hip Strip, busy with cruise passengers. The more exciting nights are the local street dances and waterfront parties with dancehall sound systems, best at weekends and best done with someone who knows them.

Trinidad's nightlife is one shared gathering: rum cocktails and salsa on the steps by the Plaza Mayor, a few courtyard bars and a nightclub inside a cave above town. It is friendlier and easier to join, but each night follows much the same pattern.

Both offer plenty outdoors, but the focus differs. Montego Bay looks to the water and the estates: the marine park's reefs, catamaran trips, bamboo rafting on the Martha Brae and the hummingbirds at Rocklands. Its walking is mostly short and guided, with Cockpit Country for those who want rougher ground.

Trinidad turns towards the mountains. The Escambray rises right behind town, with forest trails at Topes de Collantes leading to the Caburni waterfall and on to El Nicho. Horse rides cross the sugar valley, and the reef off Ancon covers snorkelling and diving.

Trinidad has more on its doorstep. The Valle de los Ingenios begins just outside town, with ruined sugar mills and the Manaca Iznaga tower. Colonial Cienfuegos, Sancti Spiritus and Santa Clara with its Che Guevara memorial are each a manageable day out by shared taxi or tour.

From Montego Bay, Georgian Falmouth is a close and rewarding outing, and Negril, Nine Mile and the Appleton rum estate also make good trips. The slow, winding roads, though, mean most people manage only one or two, usually on an organised excursion.

Montego Bay is the easier choice with children, as long as you stay in a resort. Kids' clubs, waterslides and the shallow, warm water inside the reef take care of the days, and glass-bottom boats and river rafting make simple outings. Outside the hotel there is little for children, and the traffic keeps most families close to base.

Trinidad welcomes children warmly, and Ancon makes a good beach day. Rough cobbles defeat pushchairs, though, and with the heat, power cuts and patchy supplies of familiar food and medicine, it suits older children far better than toddlers.

Trinidad is simpler to get around once you arrive. Everything in the old town is a short, if uneven, walk, and many lanes are closed to cars. Only the beach, the mountains and other towns call for a shuttle, taxi or bike.

Montego Bay is quick to reach, with the airport beside the Hip Strip, but awkward after that. Resorts are spread kilometres along the coast, pavements soon disappear, and route taxis are hard to work out, so visitors rely on tourist taxis and hotel shuttles.

Neither is worth choosing for shopping, but what you take home differs. Montego Bay offers duty-free jewellery, rum and cigars by the cruise port, a craft market where haggling is expected, and the best edible souvenirs: Blue Mountain coffee and jerk seasoning.

Trinidad's lanes are hung with hand embroidery and crochet, family potters work at the wheel, and small galleries sell local paintings. It is more of a craft tradition and less of a souvenir trade, although stalls repeat themselves.

Trinidad is clearly the cheaper stay. A casa particular with breakfast costs little, the old town needs no transport, and the music in the squares is free. Paladar meals, beach taxis and tours are where visitor pricing comes in, and you need to carry cash.

Montego Bay surprises many people with its cost, because most beds are in resorts priced for North Americans and taxis and excursions add up quickly. Roadside jerk and patties are cheap, but an all-inclusive package is often the most predictable way to keep spending under control.

Trinidad has music every night, and it is the real thing. Older musicians sing traditional Cuban song at the Casa de la Trova, son and salsa bands play beside the Plaza Mayor, and Afro-Cuban rumba fills the Palenque de los Congos Reales, with locals dancing next to visitors.

Montego Bay comes alive for Reggae Sumfest each summer, one of the best-known reggae festivals anywhere. The rest of the year it is mostly cover bands in Hip Strip bars and resort shows, and neither town has formal theatre or classical music.

Montego Bay is built for rest in a way Trinidad is not. Resort spas offer treatments in open-air pavilions by the sea, adults-only hotels guard their quiet, and you can book a massage on the sand. The calm stops at the hotel gate, so choosing the right resort matters.

Trinidad's restfulness lies in shaded courtyards and rocking chairs during the long, hot afternoons. Spa options are a few hotel massages near Ancon, and roosters, horse carts on the cobbles, late music and power cuts all break the peace.