Lounge 2727 sits at 5 Jimmy Cliff Boulevard on the Hip Strip, above the sea, and runs as three things on one property: a sea view lounge and bar, a hookah room, and a licensed cannabis dispensary called Island Strains. The venue itself is recent and has no deep history, so this page is about the street it stands on and the law that lets it sell what it sells.
History
The venue is new, and we will say so
There is no founding story here worth inventing. Lounge 2727 first appears in listings and reviews around 2019 and no opening date is published by the business. It markets itself as the number one lounge in the Caribbean, which is a claim, not a fact. What is worth knowing is the address.
Jimmy Cliff Boulevard, and the man it is named for
The strip was Gloucester Avenue for most of its life and was renamed Jimmy Cliff Boulevard in 2019. Both names are still in daily use, so a taxi driver will answer to either.
Cliff was born James Ezekiel Chambers on 30 July 1944 in St James, the same parish the lounge stands in, at Somerton in the hills behind Montego Bay. He took the stage name Cliff as a teenager, went to Kingston, and by his twenties was one of the first Jamaican artists with an international audience. The 1972 film The Harder They Come, in which he played the lead and carried most of the soundtrack, did more to put reggae in front of the rest of the world than any record before it.
He won the Grammy for Best Reggae Album twice, for Cliff Hanger in 1985 and Rebirth in 2012, twenty seven years apart. Jamaica gave him the Order of Merit on 20 October 2003. He was inducted into the Rock and Roll Hall of Fame on 15 March 2010 and remains one of only two Jamaicans in it, the other being Bob Marley. He died on 24 November 2025, aged 81, of pneumonia following a seizure. The street was named for him while he was alive to walk down it, which is not how these things usually go.
Why there is a dispensary attached to a bar
Visitors are often surprised that a lounge on the main tourist strip has a legal cannabis counter on the same property. That is down to a specific and fairly recent piece of law. Jamaica's Dangerous Drugs (Amendment) Act passed in February 2015 and took effect on 15 April 2015. It made possession of two ounces or less a ticketable offence carrying no criminal record, allowed each household up to five plants, and created the Cannabis Licensing Authority to regulate a legal industry for medical, therapeutic and scientific use.
Ganja is not simply legal in Jamaica, and this is the part people get wrong. It is decriminalised in small amounts and licensed for medical sale. Buying at a licensed dispensary and smoking on their premises is lawful. Buying on the street is not, smoking in public is still a ticketable offence, and carrying any of it through the airport is a serious criminal matter in both directions. The dispensary model exists so that visitors have a legal route, and the self declaration of medical need used for overseas customers comes straight out of that 2015 framework.
What it costs and when it opens
It runs seven nights, with DJs, bottle and table service and hookah, plus a daytime lounge that is much quieter. Reliable published hours are hard to come by and the venue changes them for events, so check its Instagram or call ahead rather than trusting an aggregator listing. Guest reports put a high top table at around US$145 and an appetiser platter at around US$27, so expect Hip Strip pricing. Thursday is ladies night and Saturday is the busiest night of the week.
Table minimums and bottle service are how the good seats are allocated here, particularly the sea facing tables and the VIP spots above the floor. If you want one of those on a Saturday, arrange it during the week. Turning up at midnight and asking is how you end up standing.
What it is actually like
The draw is the position. The lounge is open to the Caribbean on the north side, so late afternoon and sunset are genuinely the best hours here and by far the cheapest way to enjoy the place. Seating is soft and low, service is attentive, the food is bar food with fried fish as the pick, and the sound system is serious once the night starts.
After about eleven it becomes a club: reggae and dancehall, a young mixed crowd of Jamaicans and visitors, and it fills. It is smaller and more contained than the big strip venues, which some people prefer and others find tight. If hookah smoke bothers you, this is not your room.
How it fits a day
We use 2727 at the two ends of the day rather than the middle. Come at around 5pm for the sunset over the water with the strip still calm, which costs you a drink and gets you the best view on Jimmy Cliff Boulevard. Or come back after 11pm and treat it as the night itself. Trying to hold a table across both is expensive and you will lose the seat during the changeover anyway. It pairs naturally with a beach afternoon at Doctor's Cave, which is a five minute walk along the same street.
