Anguilla has no right to be fabulous. The Caribbean island, a British overseas territory about seven miles north of St. Maarten/St. Martin, is a blip on the radar — a mere 35 square miles with just six traffic lights. It’s dry and flat, and its tourism scene took off only some 20 years ago; until the 1960s, after all, much of the island lacked electricity and telephone service. Yet fabulous Anguilla is home to some of the region’s toniest resorts, epicurean eateries and breathtaking beaches. It has architecturally striking villas like those at Altamer, named for exotic gemstones. And it is a magnet for celebrities like Kevin Bacon and Jimmy Buffett, a kind of British St. Bart’s.
Without the pretension, though — Anguillan style is a perfect paradox: unfussy chic, barefoot elegance. There are no cruise ships, casinos or high-rise hotels, but there is a thriving local music scene, headed by notable up-and-coming singer-songwriters like Omari Banks and Ruel Richardson, and showcased at Moonsplash, the island’s annual reggae festival. And the fabulous factor grows with every season: luxe hotel unveilings include Malliouhana, reopened late last year after a three-year overhaul, along with coming debuts of Zemi Beach Resort and Spa, an opulent 115-room resort, and the Reef by CuisinArt, a boutique hotel powered by a four-acre solar field.
1. Get to the point | 1:30 p.m.
Anguilla boasts 33 beaches so unreservedly magnificent you won’t believe they’re real. Could water be this blue, and sand this much like a white-velvet carpet? Take your towel at once to the most highly praised of them all: Shoal Bay East, a two-mile stretch crowned by “the point,” where the beach curves out in the middle, and the envy-inducing photo you’ll post will make everyone at home un-friend you.
2. Treatment time | 4:30 p.m.
CuisinArt Golf Resort and Spa is famous, of course, for its cuisine — the executive chef Jasper Schneider now offers cooking classes using herbs and produce from the property’s half-acre hydroponic farm. But the palatial Venus Spa, with its unique and extensive menu, is also a big draw. Indulge in a Warmed Seashell Massage ($140 for 50 minutes; dollars accepted throughout the island) or a Healing Waters Sea Scrub and Soak treatment ($150 for 50 minutes), which uses local salt and water as invigorating exfoliants.
3. Sunset Cocktails | 6 p.m.
When Viceroy Anguilla opened in 2009, it seemed like a slice of South Beach in the Caribbean, with all the design-forward flair one would expect of the chic global brand. You can luxuriate in a magical sunset beside an infinity pool stretching to the sea at the hotel’s Sunset Lounge, which offers an alluring collection of aged rums and Cuban cigars (specialty cocktails from $15). If you’re lucky, you’ll be serenaded by Omalie360, a local R&B band whose lead singer can give Usher a run for his money.
4. Classic Dining | 8 p.m.
As one of the first luxury properties to open on the island, in 1988, Cap Juluca — with its white Greco-Moorish arches a dramatic sight against the blue-sea backdrop — might well be the face of Anguilla tourism. Its Spice restaurant has been redone as a Moroccan lounge, complete with plush silk couches, colorful décor and a Mediterranean-themed menu featuring local seafood dishes like pan-seared scallops and grilled Anguillan crayfish. (Dinner for two averages $140, without drinks).
5. After Dark | 10 p.m.
Sandy Ground is as close as it gets to a night-life strip in small-town Anguilla. The Pumphouse is an old salt factory turned pub and live music venue; Johnno’s Beach Stop is an Anguilla institution, known for its Sunday jazz sessions; and every night of the week, you’ll find at least one other night owl at Elvis’ Beach Bar, where a 16-foot boat serves as the bar and a new menu of Mexican food staves off potential hangovers. And yes, the place is presided over by Elvis himself — you’ll spot him by the gold chains around his neck.
6. Go Down Under | 9:30 a.m.
Contrary to what the old textbooks said, the Caribbean was not “discovered” — Amerindians thrived there for centuries. Pay your respects to Anguilla’s natives by viewing Taino petroglyphs inside the island’s limestone and coral underground caves. Oliver Hodge, a local guide, offers informative tours (264-772-4252; $20 each) during which you’re likely to hear about Amerindian dentistry via something called a ram goat bush, and the Fountain Cavern National Park, thought to have been a Taino holy pilgrimage site. If you’re too deep in laid-back Anguilla mode for a trek, catch a glimpse of the Tainos — along with other Anguillan artifacts, like early photographs and old postage stamps — at the charming Heritage Collection Museum in The Valley, Anguilla’s capital ($5; under 12, $3).
7. Beach Bumming | 1:30 p.m.
In Anguilla, don’t not spend a hefty chunk of your day on a beach. Meads Bay is a popular choice, not just for its immaculate beauty — that’s hardly hard to find on the island — but for the beloved hotels situated there, including the boutique Frangipani Beach Resort. Lunch at the property’s on-site Straw Hat Restaurant ($40 for two) is a homesick New Yorker’s delight — the menu offers local favorites like red snapper ceviche and a spicy fish sandwich, but there’s also the pastrami Reuben and the “best bagel in Anguilla.” And at the end of the meal comes a stellar treat: beach chairs, perfect for lounging the afternoon away.
8. Get on a boat | 4 p.m.
Sunsets are a theatrical event in Anguilla, so take a sunset cruise with Sea Pro Charters ($350 for up to four people). Stop to snorkel at Little Bay, one of seven marine parks surrounding the island, and wave to pelicans nesting in the cliffs overhead. Then climb back in the boat, pour yourself a glass of local Pyrat rum, and take in the clouds glowing pink over a cerulean sea.
9. Fine Dining | 8:30 p.m.
Among the island’s most eminent dining experiences, Veya feels anything but ostentatious (expect to pay $150 for two without drinks; five-course tasting dinner, $95). The wooden decks and garden fountains lend the restaurant a treehouse-style vibe, and every week diners are treated to acoustic reggae sets by Omari Banks, the talented son of the Anguilla icon Bankie Banx, the musician behind Moonsplash — he sounds like something of a cross between Bob Marley and Bob Dylan. Veya’s food, though, is hardly casual: carpaccio of conch with Asian chayote slaw, vanilla-cured duck breast with guavaberry sauce and Moroccan spiced shrimp cigars.
10. Morning ride | 8 a.m.
It may be a romantic cliché — horseback riding down a pristine beach as the sun greets the morning sky. But so what? Make the fantasy come to life by booking a ride with Seaside Stables ($75 for a one-hour group ride).
11. Scilly Cay | 12 p.m.
Go to Island Harbour, a fishing village on Anguilla’s tip. Stand at the dock and wave. A small boat will sputter over to carry you to an idyllic Sunday afternoon — also known as Scilly Cay. The 29-year-old Anguilla institution is an island-off-an-island where you’ll do four blissful things: swim in serene, shallow waters; listen to live reggae music; eat — grilled lobster, fish, crayfish or chicken — and drink some lethal rum punch (lobster or crayfish $75; chicken $30). Be sure to set aside time for a laughter-filled chat with the owners, Sandra and Eudoxie Wallace, whose colorful Anguilla-back-in-the-day stories are as ribald as Eudoxie himself (with a nickname like Gorgeous, would you expect anything less from the man?).
Cap Juluca is the island’s renowned hotel, with 18 villas scattered across nearly a mile of white-sand beach, an 1,800-square-foot pool, two tennis courts and four dining and drinking options (from $595).
The newcomer CeBlue is Anguilla’s only luxury private residence club. With their blue roofs, plunge pools and hilltop location, the chic multibedroom villas bring a bit of St. Barts to the English Caribbean. (Crocus Bay; 800-304-1484; ceblueanguilla.com; from $1,000 a night for a three-bedroom villa with a three-night minimum stay).
“Budget Anguilla” is essentially an oxymoron, but there are some exceptions to that rule. For a more affordable accommodation option, try quaint Arawak Beach Inn, a 17-room off-the-beaten-path property on charming Island Harbour. (ArawakBeach.com; rates from $195.)