Margaritaville on Jimmy Cliff Boulevard was the first Margaritaville anywhere in the Caribbean, and it is Jamaican built rather than imported: two local businessmen licensed the name from Jimmy Buffett and opened it on the Hip Strip in 1995. It is loud, it prices in US dollars, and on a two ship cruise day it is heaving. If that is what you want, nowhere in Montego Bay does it better.
History
A Jamaican company that bought an American name
The common assumption is that this is a US chain outlet dropped onto the strip. It is closer to the reverse. Ian Dear and Brian Jardim, both Jamaican businessmen, opened the restaurant Marguerites on Gloucester Avenue in 1995 and built Margaritaville next door as, in Dear's words, a fun concept they felt Montego Bay needed. Dear went on to meet Jimmy Buffett and secure the licensing rights, and Margaritaville Caribbean Group has paid annual royalties to Buffett's holding company ever since. The Montego Bay site was the first Margaritaville in the region, and it claims Jamaica's first waterslide with it.
The seaplane the police shot at
The friendship behind the licence began the year after the restaurant opened, and Buffett's connection to Jamaica nearly ended violently before it started. On 16 January 1996 his seaplane, the Hemisphere Dancer, landed off Negril and was fired on by Jamaican police who believed it was running ganja. The windshield was shot out. Nobody was hit. On board were Bono, his family, and Chris Blackwell of Island Records. Bono later described it as terrifying and said he thought they were all going to die. The Jamaican government apologised once the mistake was clear, and Buffett turned the whole thing into the song "Jamaica Mistaica" on the album Banana Wind, released that June. Dear has said that of everything Buffett did, Jamaica was what he loved.
What grew out of one restaurant
The Montego Bay venue turned into a group. Margaritaville Caribbean went on to open the first Air Margaritaville at Sangster International Airport, a second Jamaican site at Island Village in Ocho Rios, and outlets in Turks and Caicos and the US Virgin Islands, alongside dozens of airport concessions running other international brands. It bought Coral Cliff in July 2018 and turned it into a gaming venue, and launched Lucky Play lottery games in February 2021. The group employed around 1,400 people before the pandemic and roughly 1,000 by 2023.
The street it sits on
Gloucester Avenue, the Hip Strip, was renamed Jimmy Cliff Boulevard in 2019 in honour of the singer, so you will see both names used interchangeably on signs, menus and taxi directions. Margaritaville's address is still commonly written as Gloucester Avenue.
What it costs and when it opens
There is no gate fee. You pay for what you eat and drink, and the water toys are included with a purchase, which in practice means buying lunch or a round. Expect appetisers from around US$18 to US$36, burgers and sandwiches around US$20 to US$22, and larger plates around US$22 to US$38. Prices are quoted in US dollars and Jamaican dollars are accepted at the day's rate.
Daytime running is aimed at families and resort guests, and the venue offers free daytime transport from most major Montego Bay resorts for groups of four or more. The nightclub, ClubVille, runs roughly 10pm to 4am with themed nights. The venue has taken the Caribbean's Leading Entertainment Venue award every year from 2018 to 2024, which tells you how seriously it takes the nightlife half of the business.
What it is actually like
Two completely different venues share one address. By day it is a deck over the sea with a long slide that drops you straight into the water, floating trampolines, a floating deck moored offshore, water volleyball and a bar that never stops. It is family friendly and genuinely fun, and it is also the busiest thing on the strip when ships are in.
By night the tables go, the sound system comes up, and it becomes a club. Reggae, dancehall and party sets, a mixed crowd of visitors and Jamaicans, and a queue at the door after midnight on weekends. The food is competent American bar food with some Jamaican plates. Nobody comes here for the cooking.
The honest criticism is the pricing. This is Hip Strip tourist pricing and it is a long way above what the same meal costs a few streets inland. You are paying for the sea deck and the slide.
The slide ends in open sea, not a pool. Water depth, swell and boat traffic vary through the day, and the trampolines and floating deck sit off the deck edge. Do not use them after drinking, keep children within arm's reach, and follow the staff when they close the water toys, which they do when the sea gets up.
How it fits a day
We slot Margaritaville as the middle of a Hip Strip day rather than the whole of it. Doctor's Cave or Dead End Beach in the morning while the sea is calm and the strip is quiet, Margaritaville from around noon to 3pm for the slide, the trampolines and lunch, then out before the late cruise rush and on to somewhere quieter for dinner. If you want the club, treat that as a separate night out entirely: come back after 11pm rather than trying to hold a table from lunchtime.
