An Itinerary for an Island Getaway to Anguilla

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Anguilla is a those lesser-known Caribbean island compared to some of its more famous neighbors {ahem, like the Bahamas because #bahamamama} While that may mean more limited flight schedules, it also means seclusion and gorgeous {not super populated} beaches — the perfect winter {or any time of year} escape for sun, sand, and peace + quiet. Keep reading for everything you need to know about an island getaway to Anguilla. 

anguilla travel getaway

How to Get There

While getting to Anguilla is not always the easiest to get to, it is definitely worth the trip.  The runway at Clayton J. Lloyd Airport in Anguilla is not large enough to accept commercial jets, so you have a few options for how to get there — fly directly into Anguilla from a neighboring Caribbean island on a smaller prop plane or fly directly into St. Martin and take a ferry boat over.  The ferry is about 45 minutes and is a really fun way to travel and clear your lungs of all that airplane air while sipping a rum punch in the sunshine {sounds solid to us}.

Where to Stay

Malliouhana {Meads Bay}

anguilla getaway

Perched at the opposite end of Meads Bay from the Four Seasons, Malliouhana is a gem atop a cliff. This resort is a retro decor lovers paradise — painted rattan chairs in cool ocean tones, mirror tiles in the floors, and bold stripes at the pools decorate the property. Although the beach is a few steps down the hill and not right out the front door, it is worth every step. The beach is bluer than you can imagine and with no major resorts aside from the Four Seasons sharing the beach, you will have the beach almost completely to yourself.

Four Seasons Resort Anguilla {Barnes Bay, West End}

The Four Seasons Anguilla is undoubtedly one of the most beautiful resorts in the world.  Located at the end of a point, the resort is sandwiched between two beaches: Meads Bay and Barnes Bay. The resort is peppered with spectacular artwork everywhere you turn. The property’s original owners carefully constructed the resort, filling it with sculptures costing millions of dollars and artwork that should be hanging in the Louvre. But don’t worry  — the resort still has a very seaside, casual feel. Sit in the Sunset Lounge for the most perfect view of the sun setting.

Belmond Cap Juluca {Maundays Bay}

Suites with their own pools and stand-alone villas are sprinkled up and down the beach at Cap Juluca. The resort recently got a complete makeover and the new look is stunning. The Belmond brand is synonymous with refined luxury around the world and Cap Juluca is no exception.

Read More: How to Eat Healthier While Traveling {It’s Possible, Promise!}

Where to Eat

sandy island

^ Some of the delicious crayfish you can get in Anguilla!

Despite Anguilla’s small size and very small population, it has some of the best restaurants in the entire Caribbean. Choosing where to eat will likely be a lengthy and difficult decision, but these are a few of the best:

Blanchard’s {Meads Bay}

Blanchard’s is one of the most popular restaurants in all of Anguilla and for good reason. Bob and Melinda Blanchard opened up this joint back in 1994 when they sold everything they owned to move to Anguilla. They serve up local specialties like grilled Anguillan crayfish in the restaurant’s adorable cottage setting. If you love their food but want a more laid back meal, consider visiting their beach shack located adjacent to the main building for some more casual seaside fare.

Veya {Reverend Carty Road, Sandy Ground}

The owners of Veya have dubbed its food as the “cuisine of the sun”, which means you can expect a lot of exotic flavors, some you’ve probably never tried before. Indian spiced yellow pea soup, snapper sauteed with mint, and warm chocolate cake with chili demonstrate these unique flavors that the restaurant is so well-known for. The restaurant has a bit of a treehouse feel with big windows that open up to the lush grounds that surround it. Sit up in the trees and enjoy the live music that they feature every night, like local musical legend Omari Banks.

Jacala {Meads Bay}

Owners Jacques and Alain {hence the name Jacala} brought French cuisine to the Caribbean in a big way. The atmosphere at Jacala is much quieter than that of other restaurants. When guests walk in, they’ll immediately feel at home in the quiet space. 

da’Vida {Cocus Bay}

Located in the laid back and quiet Crocus Bay, elegant da’Vida is the only building to be found on the entire stretch of sand. It is truly worth the drive down the steep and windy road to get here. The fine-dining menu includes deliciousness such as seared Chinese spiced chicken, pan-seared miso grouper, and conch carpaccio.

Johnno’s Prickly Pear {Prickly Pear}

Johnno’s is not just your average restaurant that you can catch a taxi to. In order to visit Johnno’s, diners must take a boat out to Prickly Pear, a pair of uninhabited cays off the coast of Anguilla. The boat will pull up and visitors have to hop out into the water to make it onshore. Once there, it’s hard not to notice that the island doesn’t have electricity.  The restaurant operates by a generator. Guests can dig elbows deep into huge platters of fresh-grilled seafood, jump in the ocean to wash it all off, and take a walk around the island to check out the local birds that inhabit it.

See More: Weekend Getaway:  San Juan, Puerto Rico

What to Do

Although small, there is no shortage of things to do on the island of Anguilla. Here are a few must-do activities.

Visit Sandy Island

sandy island

^ The view from Sandy Island!

Standing on the beach in the little village of Sandy Ground, many likely think to themselves that Anguilla can’t get much prettier. But then they’ll ll gaze out onto the horizon and see a little speck of an island and realize that it can get much, much prettier. That little speck of an island is known as Sandy Island {perfectly descriptive} and is accessible only by boat. The tiny little boat known as “Happiness” leaves Sandy Ground every hour and heads out to this little island.

Once there, hop in the water for some snorkeling and when you come out, head straight over to the bar. You’ll likely have worked up an appetite with all that swimming. It’s the perfect place to order a big plate of fresh grilled crayfish and rice and beans, a delicious local specialty. Sandy Island is definitely one of those places visitors will be thinking about long after they’ve returned home.

Take a Day Trip to St. Martin

The best part of Anguilla is how quiet it is, but that also means there is not much by way of shopping. Consider taking a boat ride over to neighboring St. Martin and get a fill of Caribbean culture and shopping. Visit either the French side known as St. Martin or the Dutch side of Sint Maarten which is unique to this island.

Ride Tiger Boats

Picture a jet ski with essentially an inflatable bumper around the edges — that is a tiger boat. The bumper gives riders a sturdier feel and helps them feel like they won’t be knocked off. On a tiger boat, people can ride into the smaller coves that larger boats can’t get into and can really explore the coastline and that turquoise water. It’s a great way to be out on the water without being on a large boat.

Have you visited Anguilla? What have you enjoyed the most about the island? Let us know in the comments!

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As a corporate event planner, Ashley's job takes her all over the globe, allowing her the opportunity to incorporate her love of travel into her professional life. She was a Hoboken resident for 8 years before she took a quick 1.5 year intermission to pursue her dream of living in Hawaii and working at a luxury resort. In addition to trying to perfect her shaka, Ashley is usually hanging with her French bulldog Beau (he goes by Beauregard when he's feeling fancy), meeting friends out for a glass of wine, dragging herself out for a run, or working on her travel blog, The Wandering Ash.


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