Montego Bay

Montego Bay has a split personality that becomes clear about twenty minutes after landing. There is the Hip Strip — the tourist corridor along Gloucester Avenue with its chain hotels and craft markets and beach bars that sell rum punches with plastic umbrellas — and then there is the actual city that surrounds it, which is dense and loud and colorful and almost entirely ignored by the people flying in and out of Sangster International. I arrived, dropped my bag at a small guesthouse on the hill above the strip, and walked downhill toward the real town before the afternoon was gone.

Sam Sharpe Square in the old downtown is named for the national hero who led the 1831 Christmas Rebellion, a slave uprising that helped accelerate abolition across the British Empire. The bronze statue of Sharpe anchors the square, and around it the city runs at full volume — minibuses calling their routes, vendors with handcarts of sugarcane juice and fresh coconut water, women in church clothes moving with purpose through the weekday crowd. The Georgian and Victorian buildings lining the streets have the particular peeling grandeur of a West Indian town that was once very important and has since decided comfort matters more than upkeep. I love this about Caribbean architecture: its refusal to perform preservation.

Scotchies is on the main road toward Ocho Rios, about fifteen minutes east of the resort strip, and it is simply the best jerk I have eaten. Not the best jerk in Montego Bay. The best jerk. The operation is open-sided, thatched, concrete floors, picnic tables, and a series of low pimento-wood pits where whole chickens and pork shoulders have been smoking over the coals for hours. The scotch bonnet heat arrives in waves rather than all at once — it builds at the back of the throat about three bites in and then it stays, transforming everything, and underneath the heat there is sweetness from the allspice and something resinous from the wood that no gas flame can replicate. I ate three pieces of chicken, a side of festival bread, and drank two Red Stripes, and the whole thing cost less than a cocktail on the Hip Strip.

The beaches around Montego Bay are genuinely lovely and mostly crowded — Doctor’s Cave is the famous one, clear water, white sand, reasonable entrance fee, packed on weekends. Less known is Cornwall Beach a few minutes north, slightly scruffier, significantly more local, where the jerk vendor at the entrance does a good afternoon snack and the vendors are fewer. Walter Fletcher Beach hosts the Aquasol Theme Park with some water slides that look terrifying and apparently are.

Rose Hall Great House on the eastern edge of the city is a restored plantation house from the 1770s, now a tourist attraction built around the legend of Annie Palmer — the “White Witch” who allegedly murdered three husbands and practiced obeah. The historical reality is more complicated and less flattering to the colonial tourism narrative than the legend suggests, but the house is architecturally striking, the views from the hilltop are extraordinary, and the evening candlelit tours have a genuinely eerie quality that the daytime version lacks. I went at night, felt appropriately unsettled, and ate jerk chicken in the parking lot afterward from a vendor who had positioned himself with the precise timing of someone who knows when people need grounding food.

When to go: December through April is the prime window — dry season, pleasant temperatures, the reef off Doctor’s Cave at its clearest. Carnival in Montego Bay runs through April and brings a particular energy to the streets worth planning around. Summer is hotter, more humid, and aimed primarily at domestic and diaspora visitors returning home; the food at the local spots gets better and the resort prices drop.