Things to do in Montego Bay

Montego Bay’s reemerging Irie Hip Strip was recently rechristened from Gloucester Avenue to Jimmy Cliff Boulevard, celebrating the illustrious son of MoBay and Grammy winner who starred in the iconic Jamaican film “The Harder They Come”. This main thoroughfare is reinvigorated with new shops, restaurants and entertainment, positioning it once again as the place to be in Montego Bay.

Doctor's Cave Beach

Central to Montego Bay, Doctor's Cave Beach was founded in 1906 when Dr. Alexander James McCatty generously donated his 700-foot long (200m) beach property to create a bathing club in Montego Bay. At the time, it was used by the doctor and his friends, and the entrance was through a cave.

In the 1920's, Sir Herbert Barker, a famous British Osteopath published an article declaring that the waters have curative powers and that he was restored to good health after bathing there. He said the waters could cure several ailments. Doctor's Cave Beach became famous overnight as many of the rich and famous came to try the water.

The Hip Strip

The Hip Strip is home to some of the best waterfront dining spots in Jamaica, serving Caribbean and international cuisine and boasting dazzling views of the bay. In addition to checking out the natural beauty of this port city, Montego Bay offers a plethora of attractions and entertainment options from reggae clubs and Rastafarian art galleries, to gaming lounges and endless tax-free shopping.

Originally called Gloucester Avenue – named after the duke of Gloucester who had his winter home in Montego Bay – the Hip Strip has been renamed to Jimmy Cliff Boulevard after this illustrious son of Jamaica who starred in the Jamaican iconic film “The Harder They Come” and has whose fame runs to numerous reggae hit songs and a Grammy award.

Tracks & Records

Usain Bolt’s restaurant concept is home to a mix of incredible Jamaican-fusion fare, live music by the island’s top artists, and surround-sound sports on multiple screens in a vibes-driven setting, making this more than just a restaurant and bar – it’s a lifestyle destination where like-minded souls unite.


Can’t live without your Grande Iced Mochaccino? No Problem! Visit Jamaica’s first outpost of this international coffee chain to get your caffeinated fix featuring Jamaica’s own famed Blue Mountain coffee.

Coral Cliff Gaming Lounge

Try your luck at this gaming emporium offering over 120 slot machines, live entertainment and big screen sporting events. Guests can sip an array of cocktails and refreshments as they roll the dice.

Jimmy Buffet Margaritaville

“Take a bite out of Paradise” and enjoy Classic Americana and authentic jerk dishes as this popular restaurant chain from celebrated musician Jimmy Buffet.

Island Strains Herb House

Licensed by the Cannabis Licensing Authority (CLA) Jamaica, this herb house offers a wide variety of 100% local seed to sale cannabis strains suited for medical conditions with a smoker's room, and a consultation area with a medical professional for customers without an existing recommendation.


This iconic fine dining seaside restaurant is a mecca for seafood lovers. Sip from an award-winning wine selection while enjoying incredible views of the Caribbean Sea.