Share on Facebook

A Trusted Friend in a Complicated World

Why This Obscure Caribbean Island is Your Next Dream Vacation

Dreaming about spending your holiday on a small, private island? At only 16 miles long and three miles wide, Anguilla certainly qualifies as small—but instead of twiddling your thumbs in solitude, you'll be astounded by the diversity of activities, resorts, cuisine, and amenities this little island offers.

1 / 13
Anguilla beach Courtesy Anguilla Tourism Board

Off the beaten path

Anguilla (which rhymes with vanilla) is a British Overseas Territory in the Eastern Caribbean—more specifically, it’s the first in the chain of the Leeward Islands. Unless you’re traveling by private jet or originating in Puerto Rico, fly into Saint Martin, and then take a public ferry service from the Marigot Ferry Terminal in St. Martin. Alternatively, schedule a charter straight from St. Martin’s airport to the Blowing Point Ferry Terminal on Anguilla—you’ll enjoy island music, rum punch, and stunning views as far as the eye can see on your 25-minute ride north. With such an exclusive setting, it’s no wonder Anguilla is one of the 11 least-crowded islands in the Caribbean.

2 / 13
Scilly Cay Courtesy Anguilla Tourism Board

Perfect weather

While you’ll need to bring an umbrella to most Caribbean islands, you can (most likely) leave it behind when packing for Anguilla—it’s one of the sunniest spots in the region. Thanks to its flat topography made mostly of limestone, rain clouds aren’t as attracted to the area as nearby islands featuring mountains and volcanos. Plus, the cooling trade winds keep the humidity at bay and temperatures rarely exceed 90 degrees. It’s basically a desert landscape in a tropical climate. See? It really is paradise.

3 / 13
sandy beach anguilla Courtesy Anguilla Tourism Board

33 beaches

If your #vacationgoals include being a complete beach bum, then Anguilla is the island for you. While you simply can’t go wrong with any of the 33 pristine white-sand beaches, those in the know put Shoal Bay East at the top of their list. This two-mile powdery strip is perfect for strolling up and down the shoreline, and the reef makes for a fun place to snorkel through turquoise waters and marvel at the tropical fish. All of the island’s beaches are public and free to visit, so there’s no need to limit yourself to just one small slice of this paradise. For future vacations, add these other 49 best beaches in the world to your bucket list.

4 / 13
Cuisinart resort and spa Courtesy CuisinArt Golf Resort & Spa

Family-friendly resorts

What’s even more fun than splashing around with your kids at a gorgeous pool? The Splash Pad at CuisinArt Golf Resort & Spa. This brand-new wet play area will keep the youngsters—and the young-at-heart—entertained for hours. The resort also has new tennis courts and bocce courts perfect for blowing off some steam or creating a little friendly competition. And just up the beach is the Anguilla Watersports’ Aqua Park at Cove Bay, an inflatable water park made of trampolines, climbing structures, and slides which offers daily races and events. Plus, it’s staffed with a certified water rescue team for added peace of mind.

Book now

5 / 13
zemi beach houseCourtesy Zemi Beach House

Beachfront boutique hotels

For a more romantic vibe, book an ocean-view room at Zemi Beach House Hotel & Spa. Located on six acres of the island’s serene Shoal Bay East beach, guests enjoy contemporary luxury mixed with island touches. Soak in the sun at the adults-only pool—one of the 10 most beautiful infinity pools around the world—play a round of volleyball on the beach or tennis on the artificial turf courts, give your core a workout with standup paddle boarding, take a kayak out for an adventure before ending the day with a private candlelit dinner on the beach. Sunset happy hours come complete with specialty cocktails, appetizers, and live music. Don’t miss breakfast with your toes in the sand at the casual 20 Knots restaurant or a weekend dinner at Stone, the resort’s fine-dining restaurant that fuses Caribbean and Asian flavors.

6 / 13
BBQCourtesy Courtesy Jill Schildhouse, The Global Glutton

Local flavors

Anguillians take TGIF to a whole new level, by ushering in their weekends at The Strip in the Valley—a street lined with food trucks and stalls serving up unpretentious, tried-and-true recipes. The Strip buzzes with energy on Friday and Saturday nights, partially due to the thumping music, but mostly due to the locals who faithfully congregate here every weekend to catch up on each other’s lives. To indulge in all the best flavors the island has to offer, plan on a progressive-style dinner up and down the street. Start at Ken’s BBQ, where you can watch Ken grill up ribs and chicken with his homemade sauce before sitting down at a wooden picnic table and digging into your own plate. From here, follow your nose to whichever stall makes you salivate, such as Good Korma Restaurant and Sharpy’s Shake Shack. There are more options than there is room in your stomach, so pace yourself.

7 / 13
thai house spa Courtesy Zemi Beach House

Luxurious spas

To many, the fastest way to decompress from the real world is a day of pampering at the spa. For an unexpected treat, visit the Thai House Spa at Zemi Beach House Resort and Spa—this 300-year-old Thai house was flown in straight from Thailand and features the island’s only hammam (Turkish bath). Cucumber and aloe wraps soothe your skin after a day at the beach, a five-element holistic massage relieves muscle tension from a long flight, and a radiance body scrub will slough off dead skin to reveal the tropical glow you deserve while relaxing in paradise. Don’t miss the yoga classes, juice bar, and the relaxation deck furnished with bird-cage hanging chairs and loungers perfect for reading a book or dozing off in between treatments. Now that you’re in a zen-like mood, check out 11 of the most luxurious spas in the world.

8 / 13
CuisinArt Golf Club, AnguillaCourtesy CuisinArt Golf Resort & Spa

Golf with a view

Sometimes it’s better not to have too many choices on vacation—perhaps that’s why there’s only one golf course on Anguilla. The CuisinArt Golf Resort & Spa is home to an 18-Hole Greg Norman Signature Designed Champion Golf Course that offers sweeping panoramas of St. Martin and the Caribbean Sea. The holes are challenging, but the vistas make it impossible to have a bad round.

9 / 13
anguilla beachCourtesy Anguilla Tourism Board

Celebrity spotting

If you live by the general rule of thumb that “if it’s good enough for Jay-Z and Beyoncé then it’s good enough for me,” Anguilla will make you feel like the star you were born to be. The list of visiting A-listers runs deep, including Cuba Gooding Jr., Lebron James, Harry Styles and Kendall Jenner (who vacationed here together a couple years ago, sparking rumors that they were an item), Brad Pitt and Jennifer Anniston, Janet Jackson, Meryl Streep, Denzel Washington, Justin Timberlake, Paris Hilton, Leonardo Di Caprio, Sandra Bullock, Michael Jordan, Paul McCartney, Shia LeBeouf, Liam Neeson, Ethan Hawke, Uma Thurman, Robert de Niro, Jimmy Buffett, and Nas. The celebs especially love how the paparazzi don’t swarm them here, so you never know who’ll you’ll spot casually sipping an umbrella drink on the beach. If you’re on a mission to collect autographs or Insta-pics, don’t miss these 15 go-to beach vacations of the rich and famous.

10 / 13
rum tastings Courtesy Anguilla Tourism Board

Rum tasting

As with all Caribbean islands, rum is the spirit of choice on Anguilla—you’ll find it in punches, cocktails; and even desserts. If you’re new to rum or haven’t yet found your favorite brand, stop by the chic Rhum Room at Zemi Beach House for a few pointers. Just say the word and the staff Rhummelier will help guide you to palate-pleasing options from their collection of over 100 varieties from around the world, including a selection of small-batch, single-estate rums.

11 / 13
bankie banxCourtesy Anguilla Tourism Board

Island music

No trip to Anguilla is complete without stopping at Bankie Banx’s Dune Preserve beach bar, a five-minute walk east on the beach from CuisinArt. You’ll hear the legendary “Anguillian Bob Dylan” sing his reggae tunes on Wednesdays and Fridays, while you enjoy a famous Dune Rum Punch—you can’t beat the backdrop of Rendezvous Bay and the mountainous views of St. Martin across the way. Another hot spot for music every night of the week is the Sunset Lounge at Four Seasons, an open-air bar with views of Barnes Bay (that are particularly spectacular during sunset) where you can chill with a Cuban cigar while sipping cocktails.

12 / 13
local lobster anguilla Courtesy Jill Schildhouse, The Global Glutton

Local lobster

Think lobster should only be served in fancy restaurants while donning a bib? Think again! Throw a cover-up over your swimsuit (or not) and enjoy a leisurely lunch at Palm Grove Bar & Grill, known by the locals as Nat’s Place (in honor of owner Nat Richardson). Despite Nat’s allergy to shellfish, this open-air beachside shack is known for its grilled Caribbean spiny lobster (which, unlike Maine lobster, doesn’t have large, edible claws) and Johnny cakes. While your lobster is cooking, take a short stroll across the warm sand to Junk’s Hole Bay, a beach on the Atlantic side of the island that’s far more picturesque than its name would lead you to believe. Strangely, lobster used to be one of foods people hated eating 100 years ago—nowadays, it’s considered a delicacy.

13 / 13
festival del mar Courtesy Anguilla Tourism Board

Fun festivals

There’s no shortage of festivals to plan your vacation dates around—each has a different vibe and will help you better connect with the island’s culture and community. Bankie Banx started Moonsplash in the ’90s, and this weekend-long musical extravaganza is usually held during the full moon each March. The Extraordinary Eats event, which debuted in 2019, is a two-week long celebration of Anguillian food—a couple dozen participating restaurants offer a prix-fixe menu that showcases their culinary skills (dates for 2020 have not yet been finalized, so check back). And the most historic event of all is Anguilla Day, a public holiday celebrated every May 30th in remembrance of the sacrifices made during the 1967 Anguilla Revolution. The island offers a host of activities, including a sailboat race around the entire island, concerts and a colorful parade. These festivals may not make our bucket list of the best food-themed festivals around the United States, but that shouldn’t give you pause, reviews call many of them a must-do.

Book now

Jill Schildhouse
As an editor at large for Reader's Digest, Jill Schildhouse is an expert in health and wellness, beauty, consumer products and product reviews, travel, and personal finance. She has spent the last 20 years as an award-winning lifestyle writer and editor for a variety of national print and digital publications.