Anguilla is, without a doubt, the hidden gem of the Caribbean islands. And it’s on purpose. Yes, they want you to stay in the many luxury villas, dine on local flavors in world-class restaurants, party at the one-of-a-kind beach bars, stroll the brilliant beaches, and splash through the island’s immaculate waters. But, they want you to do it discretely.

If nearby St. Barts has the reputation for where the rich and famous are seen, Anguilla is the place where they (and you) can anonymously unwind in some of the best of everything the Caribbean has to offer.

How to get to Anguilla

For a destination that prides itself on privacy, it might come as no surprise that there’s no direct way to land on the island from much of the outside world. Sure, there’s The Clayton J. Lloyd International Airport. And “international” is in its name, but if you think you can fly direct to Anguilla from the United States or Europe, forget it.

The best way to get to the island is via a brief stop at the Princess Juliana International Airport (SXM) in St. Maarten. There are a number of airlines who can get you there from the United States. Both JetBlue and Delta have several flights from New York (JFK) daily while American Airlines connects out of Miami (MIA).

Once you’ve arrived in St. Maarten, it’s a short transfer to a ferry and then a quick jaunt on the water across the Anguilla Channel.

Calypso Charters Anguilla

Rum Punch with Calypso Charters Anguilla

Our favorite way to make the crossing is with Calypso. They run well-appointed shuttles frequently for $65 per adult (ages 12+) one way. Children ages 2-11 are $35 and children under 2 years old are free. The best part? A complimentary rum punch during the ride. (Here’s a tip: when you’ve finished your welcome drink, feel free to ask for another. They’ll happily oblige.)

It may sound like a lot to drive to the airport, fly to St. Maarten/St. Martin, drive to the ferry, then sail over to Anguilla, but it’s not. The direct flights to SXM are quick and the ferry transfer is a simple and pleasant affair.

Anguilla Accommodations

While other destinations may focus on high-rise hotels, this Caribbean island likes to keep things a little more low key. The primary way it does that is through an exceptional selection of villas.

For a quintessential Anguilla villa experience, check out Tequila Sunrise Villa. We loved it for its awe-inspiring and secluded location, impeccable design, gorgeous views of Saint Martin, and especially, the unstuffy vibe of the place.

Tequila Sunrise Villa – A Beautiful Beginning On Anguilla

If you’re going a little more upmarket, consider another one of our favorites: Ani Private Resorts. Here, you get the privacy of a villa (actually two villas boasting 10 rooms), but with all the amenities of a resort. Think chef, butler, masseuse, and other attentive staff committed to making your stay nothing short of magical.

But the stays here aren’t only villas. A number of stellar luxury hotels also grace the island. Our favorite options include The Four Seasons Anguilla, CuisinArt Golf Resort & Spa (yes, that CuisinArt), Belmond Cap Juluca, Zemi Beach House, plus the fully-remodeled Malliouhana. Also, worth checking out is the affordable Carimar Beach Club right on the sands of Meads Bay

Anguilla Beaches

Speaking of beaches. Here you can find some of the best white sand beaches. And not just in the West Indies, we’re talking about the best in the world! No, this isn’t hyperbole. They’re that good.

Here you can find 33 beaches with blindingly white sand. The water is pristine—crystal clear, the perfect temperature, and in many cases, calmly lapping against the shore.

What are the best Anguilla beaches?

We love (with a passion) Meads Bay Beach. It’s one of the islands widest and longest stretches of sand. Malliouhana is on one end while the Four Seasons is on the other. In the middle is Carimar Beach Club plus great spots to eat like Straw Hat Restaurant. If you’re not staying on the beach, chairs can be rented.

Another stand out for the opposite reasons, is Little Bay Beach. It’s tiny, remote, and only accessible by boat or via a death-defying climb down a rope ladder. It’s basically the thing dreams of seclusion are made of. And did I mention there’s cliff diving to be done?

Shoal Bay Beach, Anguilla

Shoal Bay Beach, Anguilla

Then there’s Shoal Bay East. It’s 2 miles of perfection. And you don’t have to take our word for it. Shoal Bay East regularly wins Best Beach in the World competitions. (With people who are into that sort of thing.) As far as we’re concerned, all you really need to know is that if you plunk down on a beach chair here (especially with a rum punch in hand), you won’t want to be anywhere else.

We also love Sandy Ground Beach for the bar and nightlife scene. The beach in Coccus Bay is no slouch either, plus it has the benefit of sporting the perfect pier for leaping into the turquoise water.

One beach we can’t say we love is Rendezvous Bay. Yes, the sand is gorgeous. And it’s huge. But for some reason, the water here is often more of a green color which, when compared to the other stunning stops on the island, just doesn’t cut it.

Anguilla Attractions

While the beaches may be the big draws here, there are plenty of reasons to explore beyond the sand.

The Anguilla Arch in the southwest of the island is a gorgeous natural wonder carved over thousands of years by wind and the Caribbean sea. Perfect for a photo op or just lazing the day away with a little rum and beautiful surroundings. Sunsets are also spectacular at this spot.

Anguilla Arch

Anguilla Arch

For some education, feel free to check out our favorite wall that proudly teaches anyone who passes about the many unique qualities of the island. Also worth checking out is Wallblake House. Claiming to be the oldest structure on the island, it was constructed in 1787 as a plantation great house. Now, visitors can arrange to tour the historic site and learn about the island’s past.

Want to really explore off the beaten path? Try taking a kayak over to Anguillita. A tiny, uninhabited island a stone’s throw from the extreme western tip of Anguilla, this is what deserted island fantasies are made of.

Another option is trying out some of the island’s many hikes. No, they may not all be marked, but for adventurous travelers, they grant access to a version of Anguilla seldom seen.


When it comes to dining on Anguilla, there’s one item that you should try on every menu: crayfish.

How can a small arid island with no freshwater rivers or lakes have crayfish? The secret is, it doesn’t!

When they say crayfish, they mean spotted spiny lobster—a smaller cousin of the standard spiny lobster enjoyed across the Caribbean. (Just don’t tell most Anguillans that crayfish are just lobsters!)

A favorite on the island, you can find crayfish on practically every menu. Trying to sample as many variations as possible in search of your favorite is part of the fun of dining out on Anguilla.

Another dining delight not to be missed is the Friday night BBQs. On roadsides throughout the island, though mostly in The Valley, grills materialize as the week comes to a close.

Anguilla roadside BBQ

Anguilla roadside BBQ

As with the crayfish, stopping at as many as possible allows you to sample BBQ chicken and incredible ribs in search of your favorite. But the best part of your search is that prices are reasonable and you can’t really go wrong bellying up to any grill you come across.

Another must-eat on Anguilla are johnny cakes. You can find these fried West Indian delights on authentic breakfast menus across the island.

I’ve had an excellent start to the day at Straw Hat Restaurant on Meads Bay with poached eggs over johnny cakes with lobster and a side salad that would blow you away.

The bottom line

A collection of some of the best beaches in the world, lux villas that wrap guests in modern elegance, delectable crayfish, and all wrapped up in a welcoming West Indian vibe — what’s not to love about Anguilla?

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