In 1976 Charles Square in Montego Bay was renamed Sam Sharpe Square in honour of national hero Sam Sharpe who was from Montego Bay. Sharpe was executed in the Montego Bay Market Place on May 23, 1832 for his role in the 1831-32 Emancipation War. The square includes several heritage structures: the Sam Sharpe Monument, the Cage, the Civic Centre and the Freedom Monument and a fountain. The Sam Sharpe Monument, designed by Kay Sullivan, portrays Sharpe holding his Bible and speaking to his people. The five statues were cast in bronze in Jamaica. They were unveiled by the then Prime Minister the Most Honourable Edward Seaga on October 16, 1983 at a ceremony in the Square.

The city's main craft market is a kaleidoscope of color. The colours that dominate are yellow, blue, purple and green. You cannot miss it. Purchase a wide range of straw and wooden souvenirs. The selection also includes T–shirts, hats, dolls and other novelties. Each brightly coloured little wooden shop is stocked with authentic Jamaican craft items. The lilt of the Jamaican accent adds a musical touch, as vendors try to get tourists to take a look and purchase a little piece of Jamaica to take back home. It's impossible to walk the streets of Montego Bay without running into a few crafts dealers, but your best bet for high quality goods is the Crafts Market at Harbour Street. This downtown area offers a variety of handmade leather, wood, and straw souvenirs. Items you are likely to encounter include straw hats, musical instruments, and beads.

Hailed as the place to party on Montego Bay's "Hip Strip" Gloucester Avenue, Margaritaville is perfect for anyone looking for an exciting night out on the town. Delicious food and a lively atmosphere make Margaritaville the place to be day and night! By day, you can enjoy international sporting events on the big screen TV's and jam to the laid back sounds of Jimmy Buffett. At night, the 'Ville swings to the sounds of the in-house DJ and partygoers strut their stuff on Karaoke, Mardi Gras and Pajama Party theme nights! The busy bar serves up a rainbow of tropically flavored margaritas and their signature 22-ounce bong of beer! Don't forget to have your Cheeseburger in Paradise!! The most popular daytime attractions are the 110ft waterslide, which winds its way from the roof above into the Caribbean below and the two giant water trampolines anchored just offshore.

Dead end beach is a popular public beach just north of Gloucester Avenue, Montego Bay. Sometimes called Buccaneer beach, dead end beach is an easy way to get an authentic Jamaican beach experience. It is basically a narrow strip of white sand over a concrete barrier at the end of a road across from Dead End Bar. The white sand does lead to relatively calm aquamarine waters but dead end is not your traditional tourist beach. Most people go there to socialize or watch the gorgeous sun set over the bay. Low-flying planes coming in to land at the airport nearby is a thrill to see and photograph. Enjoy a cold drink or a game of pool at the Dean End Bar across the street. There are no restrooms available but you may be able to use the facilities at a nearby business.