Unlike Saint Martin to the north, Anguilla does very little to entice tourists with deep pockets to spend their time and money on the island. There's hardly any nightlife, save for spots like Elvis’s, the bare-bones beach bar boat and the occasional roadside party (we recommend the informal tented bar at grocery Foods 95) you have to drive around to find. The white sand beaches and dazzling reefs are free from Jet Skis zooming through the water thanks to a government ban. The clear turquoise water is warm even in winter, and the view from any point on the island is breathtaking. Finding a reason not to relax when visiting Anguilla is difficult.
Besides turning your mind off, the best reason to go to Anguilla is the food. For an island that's barely 16 miles long and 3 miles wide, deciding on where to snag a great meal is difficult when there are dozens of spots to choose from. For such a small island that prides itself on being the most low-key destination in the region, you go to Anguilla to chill out in the sun, but you also go there to indulge.
For first-timers, the unofficial cocktail of the island is a rum punch, usually made with some combination of local fruit juices and rum. Sure, you can order up a glass of it in Jamaica or any of the other tropical islands, but stop into Roy’s Bayside Grill on Sandy Ground and order one of Joan's truly exemplary rum punch cocktails, which boasts a float of nutmeg and white oak aged Myer's Rum on top. This old school English pub on the beach has been serving them up since 1981, and the drinks are just the beginning of a laid-back meal of what might be the best crock of French onion soup you'll ever have, red snapper so fresh it practically swam into the kitchen, and a traditional side of rice and peas. If you have room, order a slice (or two) of owner Mandy Bossons' delectable coconut cake.
You can usually count on getting fresh mahi-mahi or red snapper most of the time, and the same goes for tuna. Straw Hat, located on the magnificent Meads Bay beach, serves it up at lunch in a banh mi sandwich, with pickled veggies and ponzu aioli. For dinner, start with their bigeye tuna flatbread, and follow with a grilled Caribbean lobster (they don't have the massive claws of their American cousins) caught by Anguillan fishermen in the very waters you can see from Straw Hat's beachfront patio. A meal like this, had just a few yards from the ocean, is pretty tough to beat.
Scilly Cay — a small coral island only accessible by boat, consists of a bare-bones kitchen (Scillay Cay doesn't have electricity), some beach chairs, unforgettable curry BBQ chicken, fresh lobster, and a former tennis pro owner and host who will undoubtedly flirt with your wife — is a must. The same goes for the Neapolitan-style pizza at the recently opened roadside spot, Artisan, in the Island Harbour section of the island. While there’s no beach view there, the pies and ever-changing daily specials make it worth the trek.
But if you absolutely must have the beach as the background to your meal, Nat's Place on the curiously named Junk's Hole Bay has to be on your list. This little shack at the end of a long and rocky path of tropical shrubs and cacti looks straight out of a Corona commercial. Besides the view, Nat's Place serves up spicy chicken, ribs, seafood, and the best johnnycakes on the entire island. Between Junk's Hole's clear shallow waters and colorful reefs and the food, it would be reasonable to want to revisit the spot more than once, but then you might miss out on discovering yet another fabulous spot on what could be the most relaxing island in the world.