Montego Bay: Hitting The Hip Strip

YOUR MISSION: To spend as much time as humanly possible shopping, eating, jamming and beaching on Montego Bay’s Gloucester Avenue, also known as the Hip Strip.

The Hip Strip Thinkstock


Get up early to watch the sun rise over the Strip, which borders the beach (most spots along the sidewalk provide an unobstructed view). Pop into The Pelican for a hearty breakfast of bacon-and-eggs or Jamaican ackee and saltfish.

Doctors Cave Beach Thinkstock

If you like to people-watch while sunning, drop by world-famous Doctors Cave Beach (admission: US$3). Rent a chair and an umbrella and relax on the deck or on the sand. The food court offers right-off-the-grill fare.

The Montego Bay “Hip Strip” is renowned for its restaurants and bars, and its proximity to Jamaica’s beaches like Doctors’ Cave and variety of luxurious, all-inclusive accommodations make Mo’Bay a phenomenal area to eat, drink, play and relax. Here are several Hip Strip hotspots selected by CT+L’s staff. CC image courtesy of sackerman519 on Flickr
Shopping in the Hip Strip CC image courtesy of sackerman519 on Flickr

Before dinner, grab your cover-up and sandals and sneak in some shopping. You’ll find everything from the ubiquitous “Red Stripe beer,” “We Be Jammin'” and “Life’s A Beach” T-shirts to more eclectic crafts of wood or seashell. A wealth of fine-jewelry merchants and duty-free items are present, too. Haggling is fairly easy with sidewalk vendors, who are simply happy you stopped by. American dollars are practically preferred here. Many of the shops differ only in name – the goods for sale are often similar.

Sandals Carlyle Inn


For pampering to the max, stay at Sandals Carlyle Inn, an all-inclusive resort that fronts the beach on nearby Kent Avenue. If you’d like a more simple place, the charming 30-room Coral Cliff Hotel has standard rooms for US$90-$100 per night.


The temptation to stop in each souvenir store. If you’re an impulse buyer, limit yourself to an hour or less of shopping per day. Do your homework before you buy (the shops are close enough to comparison shop quickly).

The Native restaurant CC image courtesy of sackerman519 on Flickr

Back at your hotel, arrange for a free pickup by The Native restaurant, where a feast for all your senses awaits. Jamaican cuisine, from tropical fruit plates to jerk cuisine and an authentic atmosphere are just the beginning of the experience. For a nightcap, saunter down to The Brewery, a sports bar with a tropical, everyone-knows-your-name feel. Sip their signature “Firewater” cocktail and watch the scenery become much more colorful. A live band on the patio plays original and cover music.

Margueritaville – a nightclub and restaurant Margueritaville


Night-life here isn’t for the meek. Dine at Marguerite’s, a fine seafood restaurant overlooking the ocean, then hop over to its evil twin, Margueritaville – a nightclub and restaurant with a tunnel-like sliding board that flings brave souls into the Caribbean. The late-night energy here is incredible, even if you’re a wallflower. The cover charge and drink specials vary, depending on the night of the week.

Walter Fletcher Beach Photo By Zach Stovall


Get ready for Agua Sol Theme Park at Walter Fletcher Beach. Set against a beautiful white-sand beach, choose from a plethora of activities in and out of the water: go-carting, banana-boat rides, personal-watercrafting, kayaking, pedal boats, glass bottom-boat excursions, snorkeling, beach volleyball and tennis courts (complete with a pro on hand for lessons). For MoBay’s – and quite possibly the whole country’s – best jerk food, cross the road to the Pork Pit.


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