Area
Gloucester Avenue
Montego Bay, St. James
The waterfront street most people call the Hip Strip, and the part of Montego Bay that works without a car.
Why go
It is the stretch of Montego Bay you can walk end to end. Hotels, bars, restaurants, craft stalls and two of the city's beaches sit along the same road, with the sea on one side of it the whole way.
That makes it the answer to a question a lot of first trips have: what can we do this evening without arranging anything. Very little else in the city is laid out this way.
Where it fits
This is a base as much as a destination. Doctor's Cave Beach is on it, Harmony Beach Park is at the eastern end of it, and Sangster International is a short drive from either.
It suits an arrival evening and a last evening better than a whole day. Walk it once and you will have seen what it is.
Good to know
It has three names
The street was officially renamed Jimmy Cliff Boulevard in 2019, in honour of the singer. A great deal of signage, and most businesses on it, still say Gloucester Avenue. Almost everybody says the Hip Strip. All three are the same road.
It is a working street
This is Montego Bay's own waterfront, not a resort walkway. There is traffic, there are people selling things, and that is the character of it rather than a fault in it.
The sea is on one side the whole way
Which is what makes it walkable in the evening rather than just a road with businesses on it.
Our take
Our view: this is the single most useful thing to understand about staying in Montego Bay. If you are on or near Gloucester Avenue you have a trip that works on foot, and if you are not, you have a trip that needs a taxi every time you want to do anything.
Guides that go here
More around Montego Bay
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Montego Bay A city on the water with the island's main airport in it. It can be a practical base for a first trip, especially when you want beaches, city access and the airport close together.Planning a Jamaica trip?
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