The Hip Strip, Montego Bay Attractions

Walking towards Margaritaville in The Hip Strip entertainment district, Montego Bay; credit Irie Travel

Montego Bay Attractions

Unless you know it well, consider a taxi or shuttle to visit nightclubs, lounges, and bars on The Hip Strip. If walking with friends or family at night, stick to Gloucester Avenue. Rent a car or tour operator to visit the cultural center, plantation rum estates, and other estates with Great Houses and renowned golf courses.

The Hip Strip
The Party Central destination of MoBay features ultra-lounges, nightclubs, restaurants, souvenir shops, and other entertainment. The Hip Strip is also close to many popular beaches including Doctor’s Cave, Cornwall, and Walter Fletcher beach. A number of loungers, clubs, and restaurants on the Hip Strip are well frequented by locals and visitors. Margaritaville is more than a DJ-popping restaurant & nightclub, it features a 120-foot curvy waterslide, two water trampolines, and water volleyball open during the day. Celebrities like P. Diddy, Nelly, and Tiger Woods have visited. Blue Beat Ultra Lounge features upscale Jazz and fancy cocktails. Pier 1 is a bar located on a small pier. As you walk between MoBay Proper Bar & Grill and the popular Pork Pit, notice the canon remains of an old British fort built in the 1700s — a dash of coastal defense history in modern times. Jamaican Bobsled Café specializes in pizza, burgers, salads, and platters at reasonable prices. As you might guess, the Jamaican 1988 Winter Olympics team’s winning bobsled is on display for raucous photo ops and dancing. The Brewery is a hangout for beer fans and Jamaican jerk dishes — if you don’t mind the Medieval look. Groovy Grouper bar & restaurant is located at nearby Doctor’s Cove Bathing Club, which has a small admission fee during the day but is free after 5 pm. Their specialty is a couple of dozen ways to make rum drinks, Conch Chowder, and Jerked Calamari. If you had a very active day burning calories, then you’ve earned Friday Night all-you-can-eat seafood at Groovy Grouper.
ADDRESS: Gloucester Avenue, Montego Bay
TOUR OPERATOR: For a “Ya Mon” visit to The Hip Strip, consider Travel Around Jamaica Tours

Montego Bay Cultural Centre
Its dedicated to the retention of Jamaica’s rich history and the development of its artistic treasures. It opened in 2014 to house the National Gallery West, an extension of the National Gallery of Jamaica. The National Museum West features the Montego Bay to the World Exhibit which houses numerous artifacts, particularly from Montego Bay and its environs. Like many American and Reopen museums, it also features touring exhibitions. The Freedom Monument chronicles the names of the slaves who were harshly sentenced for their participation in various uprisings for freedom. Samuel Sharpe was hanged near the front of the Montego Bay Cultural Centre for leading a major uprising. Modern Jamaicans were so impressed, that they posthumously made him a national hero and named the square in his honor. Visit Ol’ Joe Cafe in the Centre’s courtyard is home to tasty Jamaican dishes to round out the experience.
ADDRESS: Sam Sharpe Square, Montego Bay
PHONE: +1 876-971-3920 or +1 876-940-6402

Rose Hall Great House
Immerse yourself if the heritage of the island as an expert guide shares the story of this restored colonial estate. Learn about the lifestyle of the European gentry in 18th Century Jamaica. The tale of Annee Palmer, the famed White Witch of Rose Hall, would delight a Hollywood screenplay writer. Some claim that Annee still haunts the place. After a coulee taste of Witches Brew served at the house, you might believe it. Even if you’re not into historical European royalty, the invigorating tropical gardens make it time well spent. No wonder it’s popular for weddings and other social events. If ghostly tales don’t bother you, take the nighttime haunted house tour. Given brief tropical showers can occur at any time, all tours are weather permitting.
PHONE: 1+ 876-953-2341

White Witch Golf Course
Built on gently rolling hills on adjacent grounds to Rose Hall, is an 18-hole championship golf course designed by Robert von Hagge and Rick Baril. This 6,758-yard, Par 71 course is named for the plantation’s 19th-century plantation mistress, Annee Palmer. Despite her wickedness, the 200-acre course delivers a beautiful challenge to savor. Tee time bookings occur up to one year in advance for this top-rated course, MAP.
PHONE: 1+ 876-953-2341

Cinnamon Hill Great House
Take another 45-minute tour of another restored great house nearby, built in 1734 by Edward Barrett. It was subsequently owned by many wealthy British families, until it was purchased by John Collins in the 1960s, then by Johnny Cash in the early 1970s. Cash and his estate owned it until the Rollins family bought it back in 2012 after Cash passed away. Rumor has it there are ghosts living in the house too, with many stories told from the Cash and other visitors about common sightings. The fascinating Great House features island architecture, furnishings, and classic statuary. Native flowers in the garden make it a hangout for beautiful hummingbirds. The interior captures family photos and a pair of Johnny Cash’s work boots. Reservations are not required, but bring comfortable shoes for changing elevations in the estate house and grounds. Tours are weather permitting.
PHONE: 1+ 876-953-2341

Cinnamon Hill Golf Course
Course designers Robert von Hagge and Rick Baril have done it again. Enjoy seaside greens and whistling pines on the 17th hole, one of the most remarkable in all of the Caribbean. 6,758-yard, Par 71 course Built on gently rolling hills on adjacent grounds to Rose Hall, is an 18-hole championship golf course designed by Robert von Hagge and Rick Baril. This 6,758-yard, Par 71 course is named for the plantation’s wicked 19th-century plantation mistress, Annee Palmer. Despite her unruliness, the course has incredible greens to savor. Book you Tee times early for this premier course, MAP.
PHONE: 1+ 876-953-2341

Greenwood Great House
Nestled in the hills a few miles off the highway, Greenwood Great House was once owned by the family of English poet Elizabeth Barrett Browning. The 200-hundred-year-old antique-filled home is another well-preserved great house in Jamaica. Enjoy panoramic vistas of the countryside too.

Rocklands Bird Sanctuary
Photograph and hand-feed exotic species of birds. Upon arrival, guests are provided with a bottle of nectar and hummingbirds quickly descend into outstretched arms. The experience is priceless. Look for Jamaica’s national bird, the regal long-tailed Doctor Bird. Rocklands lies about a 30-minute drive away from downtown Montego Bay.
ADDRESS:: Rocklands Road, Anchovy

Appleton Estate Rum Tour
If you enjoy sampling rums of the Caribbean, then this tour should make your itinerary. Nestled in the countryside, also known as Cockpit Country, Appleton Estate serves up a rum with a unique Nassau Valley flavor sure to satisfy cocktail enthusiasts. The landscape is a marvel to behold. It’s a pleasant ride from MoBay or Ocho Rios. Be sure to select a Designated Driver, taxi, Uber, or tour operator for this venue. Delicious rum tastings can sneak up on you.
PHONE +1 876-963-9012

Reputable Tour Guide

Leo Tours
Sangster Airport Transfers, Taxi services, nightlife/parties, plus excursions to Appleton Estate, Dunns River Falls, Nine Miles, Blue Hole, Martha Brae River, Jamaica Reggae Ride, Rose Hall Great House, YS Falls, Ricks Cafe, The Hip Strip, Mystic Mountain, Swamp Safari Village
ADDRESS: Montego Bay
PHONE: +1 876-586-4149


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