Margaritaville Montego Bay

Fridays here are Montego Bay’s biggest party of the week, live music and harbor views over one of Jamaica’s most active ports.

Named for the pirate who sailed with Anne Bonny and reportedly lost his ship because the crew was drunk — Calico Jack’s island bar on Runaway Bay captures that same spirited energy.

A public bar on the grounds of a Negril villa, with no floor but sand, a thatch roof hung with years of customers’ T-shirts and license plates, and cold Red Stripe about twenty feet from the water.

Negril can be a lot – even by Negril standards – but Woodstock (officially the Woodstock Negril Lobster Shack) offers a genuine break from the intensity without losing any of the Seven Mile Beach energy. Settle into a lounge chair or camp out at the bar for the people-watching; either way, the staff banter alone is worth the visit. Breakfast on the beach with an actual coffee program, a nine-rum-deep cocktail list, and a lobster shack menu that goes well beyond the usual jerk-and-burger rotation. Live music runs frequently through the week. Chill, welcoming, and exactly the ‘Negril chill’ advertised.

Since 1974, Rick’s Cafe has been the definitive answer to ‘where do we watch the sunset in Negril?’ — cliff diving, Red Stripe, and that view that makes you question every life decision that didn’t bring you here sooner.