Anguilla’s Dune Preserve is my idea of what a great beach bar should be.

It is the type of discussion to have with a few friends, perhaps with a glass of rum, a cold Carib or a chilled mango juice in your hand. What makes the perfect Caribbean beach bar?

Everybody might have their own opinion on the subject, but there can be no doubt that the image of the Caribbean beach bar is an iconic one. One with a unique, enduring appeal that touches locals and visitors alike. They have been dreamt about, written about and celebrated in countless songs over the years.

It’s a question that seemed particularly pertinent this year as my wife and I finally completed a long-wished-for bucket list trip – a beach bar crawl of Tortola and Jost Van Dyke in the British Virgin Islands. We visited 14 bars in seven days, including such legendary names as the Soggy Dollar, Ivan’s Stress Free, Gertrude’s and the grandfather of them all, Foxy’s – a few more than once.

So, what is the answer?

Our June trip included, I have visited, enjoyed and written about beach bars on more than 40 islands, and here’s my, admittedly very personal, take. For the perfect Caribbean beach bar, all you really need to start with is a beach and a bar. And then add that one more, somewhat indefinable, ingredient. But I’ll get to that later.

The popular image is of a rickety wooden hut with a bamboo bar and palapas scattered on the sand among the palm trees. Now, I’ll admit that there are some excellent bars located on beaches around the Caribbean that wouldn’t look out of place in Architectural Digest (Barbados’ Lone Star and St. Barth’s Nikki Beach, for example), but that’s not what we are really talking about. 

We are talking about that simple waterside shack. A place to sit back (perhaps with toes in the sand), with a cold drink in your hand, an ocean breeze in your face and good music playing in the background. Quite simply, a place to lime. And that could mean just hanging out with a few friends or, as in the case of many vacationers, simply soaking in the sun and scenery, and letting the everyday stresses of back home sail off into the sunset.

Since we are talking about bars, drinks obviously need to be considered. Local beer and rum (the Caribbean has many excellent examples of both) are essential. Perhaps throw in a couple of original cocktails like the Painkiller and the Killer Bee. Music is also a key ingredient. It must be island music. Not just Bob Marley, as indispensable as he is. There is so much more to Caribbean music than reggae. There’s calypso, soca, ska, zouk, reggaeton, kompa and more. And, this is important, it should never be too loud. Certainly, never loud enough to drown out conversation.

But these are add-ons. The core of the beach bar comes down to that other ingredient I hinted at. For want of a better term, let’s just call it authenticity – being true to the spirit and character of its location. And that means not just the Caribbean, but the individual island. That authenticity can’t be bought or added in a remodelling. It has to be there from the start. As such, it often comes from the people who conceived and built the bar in the first place. And many of those islanders behind some of the most famous beach bars are as legendary as the places themselves. 

There’s the British Virgin Island’s Foxy Callwood. Back in the ‘60s, noticing the increase in boaters visiting tiny Jost Van Dyke, he set up beside his mother’s fruit and vegetable stand with a sign saying “Mom’s Booth, Foxy’s Bar. Drinks 25 cents”. A sailor cum entertainer cum bar owner, he has steadily built Foxy’s into perhaps the world’s most famous beach bar over the years, earning the Order of the British Empire along the way and even making his way into the lyrics of a Jimmy Buffett song.

Foxy’s on Jost Van Dyke in the British Virgin Islands may just be the most famous beach bar in the world.

Or Llewelyn ‘Sunshine’ Caines, who started out sailing to Nevis from his native St. Kitts every day to deliver food to workers rebuilding the hurricane damaged Four Seasons Resort. Then, with a steel drum barbecue and $40 worth of beer and chicken wings, he decided to set up on the adjacent beach. With his engaging personality and a few marketing tricks (e.g., paying local children to chase down beach goers and bring them back to the bar), he steadily built his business. Today, Sunshine’s is world famous, the walls adorned with photos of its always-smiling owner posing with presidents and prime ministers.

Llewelyn ‘Sunshine’ Caines is the king of Pinney’s Beach in Nevis.

Local reggae-folk musician Bankie Banx, the owner of Anguilla’s Dune Preserve, wanted to preserve some pristine Anguillan beach front from development by the mega resorts and condos that were springing up on either side. He bought the land, build the appropriately named bar and settled in. The Dune Preserve is still going strong (despite being virtually washed away by Hurricane Irma in 2017), playing host to the annual Moonsplash music festival that draws visitors from across the Caribbean and around the world.

Then there’s Basil Charles of Basil’s Bar in the Grenadines. Moving, virtually penniless, to the undeveloped Mustique from his native St. Vincent, he was hired as a bartender by the eccentric British aristocrat Lord Glenconner, who had just bought the island. Despite a sometimes-tumultuous relationship with his employer (including the occasional fist fight), he was put in charge of a new waterside bar, named in his honour. In the early ‘80’s, it became Basil’s Bar in more than just name. Although he no longer owns it, Basil is still occasionally around, reminiscing about serving cocktails to Princess Margaret, David Bowie and Mick Jagger, and being a guest at William and Kate’s wedding.

And let’s not forget the ladies. There’s Gwen Webster who built Gwen’s Reggae Grill on beautiful Shoal Bay East in Anguilla. When it was washed away, she rebuilt it, only to have it burn down. She rebuilt it again. Another hurricane and another (stronger) rebuild and it’s still going strong today, deservedly famous for its ‘Scratch Band Sundays’.

The irrepressible Gwen Webster has overcome fire, beach erosion and hurricanes to keep her Reggae Grill an essential stop on any visit to Anguilla.

Grenada’s Esther Charles somehow transformed her father’s small grocery stand on Grand Anse Beach into the impossibly tiny but bustling Esther’s Bar, perhaps the island’s best and a constant on Top Ten Caribbean Beach Bar lists.

Furthermore, much respect is due to a pair of sadly departed pioneers: the larger-than-life Gertrude Callwood, who opened one of the first establishments on that beach bar Nirvana, White Bay in the BVI, and Miss Emily, who invented the Goombay Smash at her cozy Blue Bee Bar on Green Turtle Cay in the Abacos, Bahamas.

With characters like these behind them, no wonder so many Caribbean beach bars are special places. Of course, most have evolved from the simple shacks and humble origins, but the best ones – the authentic ones – stay true to their roots.

Is there a perfect Caribbean beach bar? Probably not, but that won’t stop me looking. To paraphrase Jimmy Buffett: “There’s too many bars to see waiting in front of me and I know that I just can’t go wrong.”

Ian Corks 2025