Montego Bay

Jamaica is the birthplace of the all-inclusive resort, and the range of properties in Montego Bay reflects that legacy. At the romantic end, adults-only Secrets Wild Orchid (Lot A59 Freeport) is well suited to loved-up couples; its secluded location and colonial style ooze grown-up appeal. Well-heeled crowds go to celeb favourite Round Hill Hotel and Villas (John Pringle Drive) for the Ralph Lauren-designed private villas, complete with maid and private pool. Those on more modest budgets should try the Doctors Cave Beach hotel (Gloucester Avenue), a stone’s throw from the beach and in the heart of the action on the Hip Strip, or the more secluded Atrium at Ironshore (1084 Morgan Road), with its on-site, British-style pub.

Gloucester Avenue, aka the Hip Strip, is where most of MoBay’s souvenir shopping action is concentrated. Pick up trinkets here but head to the Old Fort Craft Park (Howard Cooke Boulevard) or the Montego Bay craft market (Harbour Street) for handmade souvenirs. The upscale Half Moon Shopping Village (Half Moon Plaza) is stuffed with chic boutiques such as fashion store Mezzaluna, whilst Holiday Village Shopping Centre (Rose Hall Road) is worth a visit to pick up duty-free purchases; both have fixed prices. No holiday to Jamaica is complete without a bottle of rum – special editions can be picked up during a tour of the Appleton Estate (Siloah P.O., St Elizabeth).

With such a plethora of all-inclusive properties, it’s tempting to just eat in the resorts, but in Jamaica it pays to get out and experience the authentic cuisine. People travel far and wide for a dish of jerk chicken from legendary street side shack Scotchies (Falmouth Road), whilst roadside vendor Pork Pit (27 Gloucester Avenue) does drool-inducing takeaway jerk pork. For a special treat, try Robbie Joseph’s Seahorse Grill (Sunset Drive, Freeport) – nab a candlelit table at the water’s edge and enjoy the harbour views. At night, the Hip Strip comes alive. At Jimmy Buffett’s Margaritaville (Gloucester Avenue), the average food is outshone by the margaritas and the 35m waterslide into the ocean – inauthentic maybe, but lots of fun.

Jamaica Jazz and Blues Festival

January

Having attracted big international stars such as Mary J Blige and John Legend as well as domestic talent, this is fast becoming one of the biggest events in Jamaica’s musical calendar.

Montego Bay Yacht Club Easter Regatta

April

Whether you’re a boat enthusiast or decidedly happier on firmer ground, the annual four-day race around the bay is always a delight to watch. Those brave enough to have a go can join in.

Caribbean Shrimp Festival

July

Seafood fans will be in their element at this festival, where attendees can try shrimp all ways – fried, peppered and curried are just some of the options. There’ll be arts and crafts workshops going on, and a cook-off, where you can watch as shrimp fans pit their skills against one another.

Reggae SumFest

July

During the summer, the Freeport area of Montego Bay transforms from unloved wasteland into buzzing party town as the reggae beats pulse through the streets, attracting legendary artists to perform to the crowds of music lovers and free spirits.

Jamaica Restaurant Week

November

Spanning Montego Bay, Ochos Rios and Kingston, Jamaica Restaurant Week sees over 75 of the island’s restaurants offering a selection of special deals on dishes, in a bid to show off the best of Jamaican cooking.