Anguilla has a reputation for upscale hospitality, but visitors can also let their hair down at some excellent beach bars, including a couple located on tiny islands just offshore.
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Sandy Island is a bit more difficult to reach than Scilly Cay, but it's also more lovely. A $10 water taxi from Sandy Ground is available, or you can arrive via your own private boat or local charters. Once here you'll find a surprisingly diverse menu at the restaurant and a bar stocked with multiple varieties of beer, a decent wine selection, and an array of Caribbean rums. Stick around for an afternoon on the broad sandy beaches that give the island its name, or plunge into the Caribbean for some fine snorkeling.
Elvis' Beach Bar
You'll see the sign for Elvis' Beach Bar just down the road from the Pump House, but not the bar -- it's actually down a driveway past a private home and right on the Sandy Ground waterfront. You'll inevitably find owner Elvis himself behind the boat-shaped bar, pouring his homemade "mamawana" shots and rum punch alongside Mexican grub. Elvis is a fan of both The King and American football (particularly the Baltimore Ravens), so this is the place to be on Sundays during football season, where you can watch the games on the big outdoor TV.
The Dune Preserve
The creation of Anguillan reggae legend Bankie Banx, the Dune Preserve sprawls in all of its multilevel driftwood glory along the waters of Rendezvous Bay. As much a concert venue as a beach bar (and an art gallery, too), the Dune Preserve is great for live music, especially if you get one of the coveted tables overlooking the stage. Performances by Bankie and his son, Omari, take place regularly (expect to pay a cover of $20 or so), and a variety of visiting international musicians also have played here during the annual Moonsplash festival, including Jimmy Buffett, John Mayer, Toots and the Maytals, and Black Uhuru.
There are actually two Johnno's -- the original on the beach in Sandy Ground, and an outpost on Prickly Pear Cay. Both are famed for their whole grilled snapper. Both are fun hangouts, with the in-town bar offering the benefit of convenience and the offshore one serving up some excellent diving opportunities along the wreck-strewn Prickly Pear Reef.
Palm Grove/Nat's Place
Not much on Anguilla is more off the beaten track than the Palm Grove (a.k.a. Nat's Place), an in-the-know beach bar at the end of a bumpy, unpaved road at Savannah Bay. Nat himself is the cook and his family helps run the bar and restaurant -- the house specialty is crayfish topped with Nat's own hot sauce, but the lobster, ribs and chicken also come highly recommended. If you're exploring the quiet east end of Anguilla, this is a must-find and a discovery that you can brag about to your friends back home.
The Sunshine Shack
Also known as Garveys, this rasta-flavored bar on Rendezvous Bay serves frozen drinks and beach food and is best known for its variety of water-sports options -- the Garvey boys work the grill, pour the drinks, and operate the banana boat, respectively. You can easily walk from here to the Dune Preserve, or vice versa.