If I was inclined to award stars to the beach bars featured on this site (I don’t for reasons explained in the intro to Beach Bar Bingo), Gwen’s would get five out of five for tenacity alone. Gwen’s has survived, among other things, beach erosion, a devastating fire and more than one hurricane, including the destruction of Irma in 2017. Yet Gwen Webster, as the saying goes, keeps calm and carries on. She picks up, moves (they are now further west down the beach) and rebuilds (with a bit more concrete than before) as required. And I’m glad she does, because Shoal Bay East just wouldn’t be the same without Gwen’s Reggae Grill.

Of course, Gwen’s has much more to offer than simply its owner’s resilience. It’s a nifty place, funky and relaxed at the same time. In fact, some people find it a bit too relaxed. It’s not the place to go if you are in a hurry, or if you like waiters hovering around anticipating your every need – or even if you like waiters. But if you don’t mind going to the bar when you need a drink, sitting back, taking your time and soaking in your surroundings, you won’t find many better places.

It’s a bright, breezy establishment. There’s plenty of room. In fact, it’s hard to determine where exactly Gwen’s ends. You can choose from picnic tables, deck chairs or hammocks in the shade or on the sand. It’s on a glorious beach and the walk from the water to the bar and back is a short one. It’s generally a nicely mixed crowd of regulars and first timers. If you are in the mood, it’s the kind of place you can stay most of the day, enjoying the occasional dip along the way.

What will you have?

Beer:  A full selection of ice-cold brews, with Carib, Corona and Red Stripe upfront.

Rum/Cocktails: A standard selection of beach cocktails and island rums, all of a decent or better quality. Gwen’s rum punch is pretty famous, and justifiably so. One difference is that the rums used are higher end than the ones most beach bars would assign to a rum punch. Take note, you other guys!

Food: The menu is primarily BBQ-based, including a selection of items from the outside grill, such as fish, lobster, chicken and ribs, though the popular menu items sell out quickly on busy days. You may wait a while for your meal. but at least you can do so knowing that when it arrives it will be delicious.


The joint is literally jumping on Sunday afternoons, when it features live music from the local Anguillan Scratch Band, who play fun minimalist riffs on reggae and island favourites. It’s a great little family-friendly party, with dancing on the sand, in the sea…wherever. They play from 1:00-ish to whenever everyone’s had enough.


Gwen’s is a much-loved institution on Shoal Bay, and deservedly so. Personally, I feel no visit to Anguilla would be complete without spending some time chillin’ at Gwen’s Reggae Grill.

IC 2019