MoBay, as it’s locally known, nestles between the gently sloping Bogue, Kempshot and Salem hills, and extends some eight kilometres west to the haunts of the suburban rich at Reading and to the plush villas and resorts of Ironshore and Rose Hall sixteen kilometres to the east. Planeloads of foreigners flood in every day, seduced by a heavily marketed Caribbean dream of swaying palm trees, lilting reggae and cocktails at sunset, and although the flow has slowed a little in recent years (with many heading straight for the more expansive charms of Negril), the city in many ways still delivers. It has achieved fame as the base for Jamaica’s summer reggae festival, Sumfest, while the Air Jamaica Jazz and Blues festival and the college antics of Spring Break inject shots of adrenalin at other times of the year.

Montego Bay itself is made up of two distinct parts: touristy Gloucester Avenue, vigorously marketed as the “Hip Strip”, and the city proper, universally referred to as “downtown”. The split between the two is so sharp that the majority of tourists never venture further than the Strip on foot, dividing their time between the unbroken string of beaches, shops and restaurants, though the air of enforced tourist-friendliness can be a bit disquieting. Downtown offers a more accurate and vibrant picture of Montegonian life, and, though it’s short on specific sights, the malls and markets here provide MoBay’s best shopping possibilities. MoBay’s holiday mask slips along its western stretch, an ugly sprawl of factories and gas containers, whose main concession to the tourist trade is the Freeport cruise ship pier.

Brief history

When Columbus anchored briefly in Montego Bay in 1494, he was charmed enough to name it El Golfo de Buen Tempo (The Bay of Good Weather). The Spanish were less romantic, dubbing it Manterias, a derivation of manteca (pig fat), after the lard they produced and shipped from here in large quantities. Eventually, the English corruption, “Montego”, stuck. By the time the Spaniards hastily fled the island, the city was little more than a village. Its subsequent development was heavily influenced by two factors. First was the presence of the Maroons in neighbouring Cockpit Country, an African-Jamaican band of militarily skilled former slaves whose frequent attacks on British settlements kept the town from prospering until the peace treaty of 1739. By this time, plantation sugar production was booming, the harbour was thronged with ships, and lavish cut-stone town houses and inns were spreading back from the waterfront. The 1831 Christmas Rebellion nonetheless nearly destroyed it. The most important of the violent slave revolts that prefaced emancipation began in the foothills behind the town, and saw almost every estate in the area burnt to the ground.

After the collapse of the sugar trade, Montego Bay spent a hundred-odd years in limbo, and it was not until the early twentieth century that it entered another period of growth, beginning when Sir Herbert Baker advocated the redemptive powers of the Doctor’s Cave waters, north of the city’s centre. MoBay metamorphosed into the ultimate tourist town; rich North Americans and Europeans built holiday homes around Doctor’s Cave, or arrived on banana boats to stay in the town’s first hotel, the Casa Blanca. The town’s population increased fourfold between 1940 and 1970, with Jamaicans from all over the island moving in to work at the hotels. In the 1960s, the Freeport peninsula in the south was constructed on reclaimed land, assuring its position as a premier port of call for Caribbean cruises. The beaches were attractively overhauled in the 1980s and 1990s, and, determinedly tourist-friendly, MoBay feels on the upswing.

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