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Montego Bay

Montego Bay is located about 12 miles east of Anticipation Villa and the Tryall Club. This city is rich in Jamaican culture and history. The first settlers were a group of Native Americans known as the Arawaks, who inhabited Jamaica and frequented the beaches of contemporary Montego Bay. Christopher Columbus sailed into Montego Bay in 1494, whereupon he named it el Gulfo de Buen Tiempo (Fair Weather Bay) [i]. The Spanish settled the area and began hunting the plentiful wild boar found on Jamaica and exporting pig lard [ii]. The contemporary Montego Bay area was soon referred to the as Lard Bay. In fact, Montego derives from the Spanish word menteca, meaning lard [iii].

Montego Bay grew into a busy, successful trading port visited by 150 ships each year by the end of the eighteenth century [iv]. The main export was sugar, and later bananas [v]. By 1908, Montego Bay began to advertise itself as a tourist destination as trade decreased. Many small hotels sprung up around Doctor’s Cove, a bathing club which valued the curative powers many people believed sea water possessed. Doctor’s Cave is still open today as a beach [vi]. During the 1950’s an airport was added to an airstrip which was built during WWII and Montego Bay quickly became a popular travel location for the rich and famous [vii].

Vacation Ad, Circa 1950

Montego Bay is most easily accessed by Tryall Club’s off-site shuttle service. Once in Montego Bay, there is a variety of shopping which from which to choose. Whitter Village in Ironshore offers some upscale options. Handicrafts set up shop on St. James Street, the Hip Strip on Gloucester Ave., and in the Montego Freeport near the shore. Many of these shops are duty-free and offer a range of products, from luxury goods to handmade crafts.

One of the famous Margaritaville restaurant locations is on the Hip Strip in Montego Bay. Based off the iconic Jimmy Buffet song, this restaurant offers affordable food and drinks, as well as a waterslide and a nightclub (+18).


There are several historical sites to visit in Montego Bay. The Bellefield Great House and Garden is located on Fairfield Road in outer Montego Bay. Bellefield was originally built in the 1600's as a military outpost before becoming a sugar plantation [viii]. We would be happy to assist you in organizing a visit to Bellefield during your stay with us.

Bellefield Great Hall

Rose Hall is another plantation located in outer Montego Bay. Built in 1770 by John Plamer, the estate was inherited by John Rose Palmer and his wife, Annee. According to legend, Annee Palmer practiced witchcraft and murdered Palmer. She remarried and murdered two additional husbands and numerous lovers [ix]. Annee became known as the White Witch of Rose Hall. Many believe that she haunts the estate to this day. Rose Hall offers both day and night tours of the estate featuring the White Witch. Please note that the Tryall Club is partnered with the tour company, Island Routes, which provides regular tours to Rose Hall. You can book a tour to visit Rose Hall during your stay with us at Anticipation.

Rose Hall Great Hall

Montego Bay is a wonderful city, rich in Jamaican culture and history. We hope you can make time to visit it during your stay with us at Anticipation.

Recommended reading material: Tour Jamaica, Margaret Morris

[i] “Montego Bay: Excerpted from the book Tour Jamaica by Margret Morris.” discoverjamaica. discoverjamaica. Web. 28 Jun 2015.

[ii] “Montego Bay.”

[iii] “Montego Bay.”

[iv] “Montego Bay.”

[v] “Montego Bay.”

[vi] “Montego Bay.”

[vii] “Montego Bay.”

[viii] “History.” Bellefield Great House and Gardens. Bellfieldgreathouse. Web. 13 Sept. 2016.

[ix] “Discover the Legend of the White Witch.” Rosehall. Rosehall. Web. 13 Sept. 2016.

#MontegoBay #BellefieldGreatHouse #RoseHall #WhiteWitchofRoseHall #DoctorsCove #Shopping #HipStrip #Margaritaville #Jamaica #Culture #History

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