Hip Strip (Gloucester Avenue)

As the main hub of tourist activity in Montego Bay, expect jubilant crowds, thumping reggae music, free-flowing rum drinks and Red Stripe, and shopping galore, from high-end duty-free boutiques to trinket stalls. A popular destination is Jimmy Buffett’s Margaritaville, a double-decker bar with giant water trampolines and a 120-foot (37-meter) water-slide that plunges into the warm waters of the Caribbean. The Strip’s best bet for live music (and martinis) is the Blue Beat Jazz Lounge, where revelers have a romantic view of the sea.

Travelers have many options to experience the Hip Strip as part of half-day, full-day, group, or private tours that may incorporate a visit to Rocklands Bird Sanctuary, a local artisan market, a nearby beach like Doctor’s Cave or Agua Bay, or a place to admire a panoramic view of Montego Bay. Other tours may include a Jamaican meal at a local restaurant.

• The Hip Strip is ideal for party-goers visiting Montego Bay. It’s a lively area, so it might not be suitable for those looking for a mellow, off-the-beaten-track experience or for small children.

• With so many shops selling similar souvenirs and t-shirts, feel free to gently haggle for better prices.

• Along the Hip Strip are access points to popular beaches like Cornwall or Doctor’s Cave. Some beaches have small admission fees that would be included if visiting as part of a tour.

• While safer than the downtown area of Montego Bay, use your discretion and stay in the more populated areas, especially at night.

Montego Bay’s Hip Strip runs along Gloucester Avenue, from Aquasol Theme Park to Sangster International Airport. It is walking distance or a quick taxi ride from many nearby hotels (some of which offer free shuttles).

A hot spot day and night, the best time to visit the Hip Strip depends on whether you want to incorporate a stop at the beach or a night out on the town. The warm months of winter comprise the busiest time of the year.

One of the best-reviewed Hip Strip souvenir shops is Tropical Treasures, where owner Sammie makes you feel at home—and has even been known to give discounts for smiling. Travelers say the prices here are fair and that his no-hassle attitude is a welcome pleasure.