The Best Bars in Montego Bay, Jamaica

Photo of Sarah Holt
25 August 2021

Gloucester Avenue, aka the Hip Strip, is the epicenter of the drinking scene in Montego Bay. This main drag is flanked by more than 30 bars; many of them stay open till the early hours. Not a party animal? There are some low-key bars in the city, too, including a pour-your-own wine bar and a floating bar-restaurant. Here’s our pick of the best of both worlds.

Jimmy Buffett’s Margaritaville

Bar, Cocktails, $$$
Margaritaville bar/restaurant, Montego Bay, Jamaica, Caribbean.
© a-plus image bank / Alamy Stock Photo
“Ice cold drinks served with red hot fun” is the slogan at Jimmy Buffett’s Margaritaville. The bar overlooks the Caribbean Sea on the north side of Montego Bay’s Hip Strip. When you want to take a break from sipping the rainbow-colored frozen margaritas, you can ride a 120ft (36m) slide from the upper terrace into the bath-warm waters below. Head here after dark and you can dance to reggae under the stars, too.

Rehab Lounge

Bar, Jamaican, Fast Food, $$$

This lively sports bar is right in the middle of Montego Bay’s Hip Strip. You can drink everything from Tia Maria to tequila here, but the bar’s most popular drinks are the buckets of beer and the mini-Guinness shots. Rehab Lounge also hosts regular mixologists, who whip up day-glo cocktails. On weekends, you can watch live music and DJ sets as you sip.

Uncorked West

Wine Bar, Wine, $$$

There are more than 150 different wines on the menu at Uncorked West in the Fairview Centre. If you can’t make up your mind about which one you’d prefer, order a wine flight. Alternatively, buy a Wine Card and you can help yourself to 30ml, 90ml or 150ml (1fl oz, 2fl oz, 3fl oz) portions of the wines in the bar’s tasting cooler. If you get peckish, you can tailor your own charcuterie board, too.

The Houseboat

Restaurant, Seafood, $$$
Jamaica, Montego Bay, Houseboat Grill restaurant, Ferry sign
© Juan Serrano Corbella / Alamy Stock Photo
This floating bar-restaurant is anchored in the Bogue Lagoon area of Montego Bay Marine Park. Most people come here for meals – however, the bar hosts a daily happy hour when there are two-for-one offers on local drinks. There’s a cocktail menu, too, which features drinks with names like the Errol Special. Whatever your poison is, the best place to sip it is on the open-top deck of the boat, where you can look out over the water.

Mobay Proper Sports Bar & Grill

Bar, Beer, $$$
This single-story bar, with its bottle-muraled outer walls, is set one road back from the Hip Strip. The weekend lasts seven days here. Expect DJ sets on Monday nights – when the area beneath the Heineken bottle chandelier turns into a dance floor – and karaoke sessions on Thursdays. The bar also offers regular drink deals throughout the week, especially on tipples like Red Stripe, Dragon Stout and flasks of rum.

Doctor’s Cave Bathing Club

Bar, Cocktails
Doctor's Cave Beach & Bathing Club, Montego Bay, Jamaica
© Mark Bassett / Alamy Stock Photo
Drinks are served to the lounge chairs at Doctor’s Cave Bathing Club on Doctor’s Cave Beach, close to the Hip Strip. You pay a minimal fee here to use the facilities – including the bar – all day. Highlights of the drinks menu include the Frozen Bob Marley cocktails that are made with rum and striped with red, yellow and green slushie, and the classic cold Red Stripe beers.

Peppa’s Cool Spot

Restaurant, Jamaican, $$$
The courtyard at Peppa’s looks out over the Caribbean Sea. Pull up a padded wooden chair at one of the parasol-shaded tables here and sip your way though a cocktail menu that features drinks like the Miami Vice, the Shark Bite and the Dirty Banana. The bar serves food, too; the menu is classically Jamaican and features dishes like steam fish and okra and jerk chicken wings.

Pier 1

Music Venue

Pier 1 is set on the waterside near Harmony Beach Park, not far from the Hip Strip. Visit during the day or early evening to enjoy a burger or sandwich and cocktails in view of the water. Make your way here after dinner on a Wednesday or Friday, however, and you can sip your drinks as DJs play a mix of music from reggae to pop.

Not got a place to stay yet? Book one of the best hotels, or one of the best budget hotels, in Montego Bay now via Culture Trip. Grab a bite to eat at the best markets in Jamaica, or catch some waves at the best surfing spots in the country, before ending your day at the best nightlife spots around.

This is an updated rewrite of an article originally by Nabila Khouri.

These recommendations were updated on August 25, 2021 to keep your travel plans fresh.

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