The Two Best Ways To Visit Anguilla

North of St. Maarten and east of Puerto Rico, Anguilla is a 35-sq. mi. slice of paradise with a barefoot casual vibe and 33 pristine beaches, many of which you can have all to yourself. So, the question isn't if you should visit this laidback outpost, but when. But, since the island has about 40 hotels and more than 70 villas, another important question to ask is, "Where will I stay when I get there?"

There are merits to both styles of stay. So, on a recent visit, we sampled both types of accommodation to help you make your decision. Thank us later.

More than 100,000 visitors come to Anguilla every year. Yet I feel as if I have the island all to myself.

That's likely because on this slice of Shoal Bay West, where the villa resort Altamer presides, there's not a single soul to be seen. It's just past sunrise, and as I stroll the shore in both directions, coffee in hand, my only company is a seagull and a couple of bananaquits chirping somewhere in the distance.

All the beaches on the island are rightfully public. But on this stretch, where Altamer is the sole villa resort and the only neighbors are a small hotel and restaurant, you wouldn't know it. Then again, privacy is the privilege for which Altamer's guests pay a premium.

The cluster of villas (which includes the five-bedroom Blue Diamond; 1.5-bedroom Petit Topaz and my digs, the five-bedroom Antilles Pearl) is a mere five-minute drive from the swanky Four Seasons. But thankfully, there's no self-conscious posing by the pool or thumping Euro-chic soundtrack here.

Instead, the music coming from the poolside Bluetooth speaker is from my own playlist, and Altamer's team of 10 (including a general manager, two butlers, landscaping and housekeeping staff) has made me feel as welcome as long-lost family, cared for in a way it's hard to equal at a large hotel.

By breakfast the second morning, butler Perry needs no reminding that I take my tea with a spoonful of honey. At dinner he remembers my preference, filling my glass with still, not sparkling water. And I barely have to glance in his direction before he appears with extra cheese to accompany my morning croissant.

With its linen sheets, Floris toiletries and fresh flowers at every turn, staying at Altamer feels like staying with a plugged-in Anguillian friend—albeit a very wealthy one. Antilles Pearl, conceived by celebrated architect Myron Goldfinger (he designed the Long Island mansion featured in the 2013 movie The Wolf of Wall Street), is a boldly geometric three-story spread, with a rooftop deck, an elevator, an enviable collection of contemporary art, and high-ceilinged, casually furnished rooms with floor-to-ceiling doors that let the light and idyllic Caribbean vistas in.

There are plenty of places to gather in the 12,000 sq. ft. residence—in the media room, with its custom pool table, perhaps?—and just as many spots (my pick: the cinematic 50-foot long skywalk that extends from the house toward the sea) where you can be blissfully alone.

But when your desire for seclusion has been sated, Altamer's staff really shines. I'd been dying to see Little Bay, a tiny north coast beach accessible only by rappelling down a cliff (yikes!) or by boat. So, villa manager Preston sprang into action, organizing a private day cruise to the winsome cove, with stops at Anguilla's famous limestone arch for photos and Sandy Island for a sumptuous lunch of the island's most famous crustacean, crayfish.

And on evenings when we weren't enjoying a private chef-prepped dinner poolside, Preston took care of reservations at island restaurants (there are more than 100 on this tiny isle, so dining out is a definite "do") including Blanchard's on Meads Bay, where fairy lights twinkling in the trees and crisply fried lobster and crab cakes are a winning combination.

Sun drunk and tired from our daily adventures, we'd return to the villa to find the air-conditioning in our rooms set to the perfect temperature, our beds turned down and a bounty of snacks available to tide us over until dinner. But it was the Mint Condition—a delectable cucumber, mint, lime and honey concoction Lavon customized specially for us—that really made us feel the way you want to feel when you're on vacation: completely at home.

Antilles Pearl sleeps 10 and starts at $22,500 per week in low season; $42,350 in high.

The expanse of Shoal Bay East—a mile-long strand that's often named one of the best beaches in the world—unfurls before me as I settle onto my chaise at Zemi Beach House, a 76-room resort that sits smack on its sands. I barely have a chance to take in the scene—swaying palms, sapphire seas and ivory sands contrasting so vividly that they look as if they've been run through Instagram's Lo-Fi filter—before a beach butler approaches with a cocktail menu. Would I like a rum punch? A complimentary fruit skewer? To take out a paddleboard?

All of those options are tempting but none more so than just lying here, soaking up the rays as a constant breeze makes palm fronds dance overhead. Besides, I've just come from Zemi's spa—housed in a magnificent 300-year-old building imported piece-by-piece from Thailand and reassembled on site—where, after a steamy session in one of the Caribbean's handful of hammams and a massage so relaxing I fell asleep almost instantly, I'm reluctant to move. For now, the beach is enough.

But if I crave more, Zemi Beach House offers plenty of other diversions. I can hop between the glass-front "mermaid" pool overlooking the sand; the tranquil adults-only Serenity Pool tucked into the bougainvillea-strewn hillside; or the Instagram-worthy plunge pool on the terrace of my own suite. A corner unit in the resort's new Building Six, its pool has quickly become the star of my Instagram stories, the hues of its iridescent mosaic tile echoing the Caribbean it overlooks from three stories above the sand.

And the action needn't stop once the sun goes down. I could swing by the Bohio Bar for some early-evening sushi and a sunset cocktail. Or I could go straight to Stone, Zemi's elegant fine-dining restaurant, where seafood and steak are served beneath what must be the largest chandelier I've ever seen. I don't normally drink rum beyond the classic rum punch, but I'm intrigued by the selection of more than 100 mostly small-batch rums served in the resort's handsome wood-paneled Rhum Bar, where a shot of 50-year-old Appleton from Jamaica will set you back $650. And I'm glad not to have missed Zemi's Wednesday-night beachfront barbecue, a cornucopia of Caribbean delights (the star of the buffet: gargantuan lobster, char-grilled and generously anointed with garlic butter) set to the soundtrack of rhythmic waves and the energetic vocal stylings of Boss and The Horsepower Band.

In many ways, staying at Zemi feels like having the best of both worlds. I'm enjoying all the amenities of a resort, combined with the (better than) home comforts of my expansive suite, which clocks in at almost 3,000 sq. ft. It has two bedrooms and 2.5 bathrooms; a fully equipped kitchen (complete with a wine fridge); a washer/dryer; an outdoor shower; and let's not forget that rooftop plunge pool.

So, in the battle between villa and resort, it's tough to say which comes out on top. Maybe I should just sit here on the sand and contemplate the conundrum a bit longer...

From $495 per room in low season, $775 in high.