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Life · 3 min read

A guide to the Hip Strip, and when to avoid it

Gloucester Avenue is the seafront mile most visitors never leave. Here is what is on it, and why locals time their visits.

The Hip Strip welcome sign, Gloucester Avenue
The Hip Strip welcome sign, Gloucester Avenue · Photo: Supplied, Placeholder — supplied by the site owner

Gloucester Avenue runs along the water on the western side of Montego Bay, and somewhere along the way it got branded the Hip Strip. It is the densest mile in the city: beaches, bars, craft shops, restaurants, hotels and the people whose job it is to get you into them.

The beaches are the reason to be here. Doctor's Cave and Cornwall Beach sit a short walk apart, both with entrance fees, loungers and somewhere to eat. Between them the street is shops, jerk, bars and the large branded places that stay loud until late.

Timing changes the experience completely. Early morning is the strip at its best — cool, quiet, the sea flat, the shops still opening. Midday on a day with several cruise ships in port is the opposite: crowded, hot, and every vendor working hard because the window is short.

You will be approached. Taxis, tours, hair braiding, craft, and occasionally something you do not want. A clear, friendly ‘no thanks’ and continuing to walk is understood and normal here; it is not rudeness and it is not taken as such.

Agree every taxi fare before you get in, and use a licensed red-plate taxi or a driver the hotel knows. Prices on the strip are higher than the rest of the city, which is the trade for walking out of your room onto a beach. Ten minutes inland, the same plate of food costs a fraction of it.

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