Anguilla Beach Bars – Gwen’s Reggae Bar, Upper Shoal Bay

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While the beach may slowly be eroding at Gwen’s Reggae Bar, an Anguilla beach bar located on Upper Shoal Bay, the affinity the locals and tourists have for this local favorite has not. Described by Anguilla Beaches as the “#1 relaxation spot of all Anguilla restaurants” and by Caribbean Travel and Life instructs us to “grab a cold drink and settle in for some serious swinging in one of the hammocks strung amid Gwen’s shady palm grove – hands down and feet up the best place on Anguilla for an afternoon nap,” Gwen’s is the perfect spot to lime away the afternoon. High on my list of beach bars to belly up to during our trip to Anguilla at Thanksgiving, I plan on doing a lot of nothing at Gwen’s and it sounds like I’ll fit right in.



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“On a prime beachfront spot on the exquisitely beautiful Upper Shoal Bay in Anguilla sits a brightly colored beach bar called Gwen’s Reggae Grill.”

About Gwen’s Reggae Bar (from Frommer’s)
“At Upper Shoal Bay, check out Gwen’s Reggae Bar and Grill (tel. 264/497-2120), which features Gwen Webster’s barbecue daily into the early evening; on Sunday it showcases live reggae performances. Ask for a side order of Gwen’s special slaw. The palm grove here is one of the few naturally shady seaside spots on the island, and it comes with hammocks.”

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Lime away the day with Gwen
Do you want to do a bunch of nothing at Gwen’s? If so, you can contact me via Beach Life Travel, the travel arm of Beach Bar Bums. For more information, email Because a beach life is the best life.

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Have you been here? If so, let me know what you think in the comments. Since it’s impossible for me to visit every single beach bar I post about on the site, the comments from readers like you allow others who are interested in checking out these beach bars hear from people who have actually been there and let them read unbiased reviews. Kind of like the Trip Advisor for beach bars!

Author: Tom W.

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  1. Thanks for sharing. Gwen’s reggae Bar and Grill is really cool. I haven’t written about it yet on my blog but will be sure to do so soon.

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    • Thanks for commenting! We’ll actually be in Anguilla on Thanksgiving for two nights before heading over to St. Martin. Can’t wait!

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      • A combo trip of Anguilla and SXM definitely sounds like fun. Who knows I may spot you somewhere during your trip as after all we are only 35 square miles. Have fun!

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