Montego Bay’s Hip Strip (Jimmy Cliff Boulevard)

The Hip Strip is Montego Bay’s tourist road: a stretch along the bay lined with beaches, bars, restaurants, craft stalls and a few hotels, a few minutes from Sangster International Airport. For years it was Gloucester Avenue. In 2019 it was renamed Jimmy Cliff Boulevard, after the reggae singer who was born in St James, and that’s the name you’ll see on maps now, though every Jamaican still calls it the Hip Strip.

Where it is and why the name changed

The Hip Strip runs along the waterfront north of downtown Montego Bay, between the city and the airport. The St James Municipal Corporation voted to rename Gloucester Avenue in April 2017, and the new name, Jimmy Cliff Boulevard, was unveiled at a ceremony on March 28, 2019, with Jimmy Cliff there to see it.

Jimmy Cliff, born James Chambers in Somerton, St James, died on November 24, 2025, at 81. For Montego Bay people the road carries his name with real pride: he’s one of the city’s own, the man behind “The Harder They Come” and “Many Rivers to Cross”.

What’s on the Hip Strip now

• Doctor’s Cave Beach: the strip’s best-known beach, run by the Doctor’s Cave Bathing Club, with changing rooms, chair rentals and calm water. Entry is US$8 for adults and US$4 for children under 12, according to the club. See the Doctor’s Cave Beach guide.
• Margaritaville: restaurant and bar by day, with a sea-side water park, and a nightclub late at night. See the Margaritaville Montego Bay guide.
• Bars, restaurants and shops: jerk spots, seafood places, cafes, craft vendors and duty-free stores line the road. For what’s worth taking home, see my guide to Jamaican souvenirs. Some businesses have changed since the 2025 hurricane, so check hours with any one you’re set on.
• Hotels: a few small hotels sit along the strip and the beaches. The Grand Decameron Montego Beach, the big all-inclusive on Jimmy Cliff Boulevard, is closed. The Jamaica Information Service reported in September 2026 that it is slated to reopen in December 2026 as Muthu Diamond Lagoon under new owners MGM Muthu Hotels; it isn’t open yet, and the owner’s website lists it as opening soon with no date.

Aquasol Beach Park, the family beach park that older guides send you to, is closed. If you want a free public beach nearby, there’s Harmony Beach Park, run by the UDC.

Free Jamaica trip checklist

Want the printable version?

Get my free Jamaica trip checklist, then guides for the part of the island you're visiting.

Leave this empty

First name

Email address

When are you travelling? (optional)Choose…In the next 3 monthsIn 3–6 monthsIn 6–12 monthsNot sure yet

Get the checklist

Unsubscribe any time.

The long-promised upgrade

The Hip Strip has been due a makeover for years. In 2021 the Tourism Enhancement Fund announced about J$1 billion to upgrade the road from Howard Cooke Boulevard to Kent Avenue, with utility lines put underground and parking garages. The work never started. Here’s where it stands:

• April 2026: the TEF’s executive director told the Jamaica Observer the project was at the design stage and was likely to move under the National Reconstruction and Resilience Authority (NaRRA), the government’s new rebuilding authority.
• September 2026: Tourism Minister Edmund Bartlett said Montego Bay’s waterfront and the Hip Strip will be “reimagined”, with a meeting with the Prime Minister on October 2, and the UDC, the Port Authority and others working on designs. He said the work had only just begun and gave no start date.

So for now, the Hip Strip looks much as it has for years: a busy, slightly worn tourist road, not a construction site. I’ll update this when there’s a confirmed start date.

Local tips for the Hip Strip

• Go to the beach in the morning. Doctor’s Cave is quietest before the cruise groups and the day crowd arrive.
• Expect vendors. You’ll be offered taxis, tours, braids and more as you walk. A polite “no thanks” and keep walking is all it takes; nobody minds.
• Use licensed taxis. They carry red PP plates. Agree the fare before you get in, especially late at night.
• Eat local. Skip the chains and try jerk, fried fish or a patty from a Jamaican spot. Prices on the strip are tourist prices, but they’re lower once you step off it.
• At night, stay where it’s busy. The main stretch is lively in the evening; take a taxi rather than walking long dark stretches back to your hotel.

Where to stay near the Hip Strip

Most visitors stay in the resorts east of the airport along the coast toward Rose Hall and come to the Hip Strip for an afternoon or a night out. For open resorts and the areas to stay in, see where to stay in Montego Bay and the best all-inclusive resorts in Montego Bay. For more to do around the city, see things to do in Jamaica.