HIPSTRIP
The "Hip Strip"or Gloucester in Montego Bay is the place to be for anyone visiting or living in Jamaica. You have about 13 hotels over, 60 shops and over 35 bars and restaurants on the Hip Strip. There are local beaches including the world renowned Doctor's Cave Beach. There are banks and car rentals facilities on the Strip as well. You can start at one end which is a dead end where you can watch the planes come in, as the runway is only yards away.
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As far as Restaurants, some include Jimmy Buffett's Margaritaville, Bob Sled Cafe, Groovy Grouper (located on Doctor's Cave Beach), Cuban Cafe, Ice's, Ma lou's, The Native, The Pelican, The Brewery, Mo Bay Proper, just to name a few. Most of these spots are open during the day. Margaritaville has a water slide, lounge chairs, water trampolines, floats, lots of entertainment and food and drink during the day and it gets wild at night.