A sparkling jewel in the Caribbean crown is Anguilla, an island that has consistently earned praise and recognition from prestigious travel publications and visitors. It continues to ride high thanks to the campaign launched by the Anguilla Tourist Board, which declares it “beyond extraordinary.”

More specifically, the board says, “There are islands. There are extraordinary islands. And then, there is Anguilla.

The island is sixteen miles from end to end, and boasts thirty-three beaches, just a few short of St. Martin. Anguilla’s proximity to St. Martin and St. Barts makes island hopping and day trips an adventure. Ferries from St. Martin pull into the turquoise waters of Shoal Bay, and you might be greeted by friendly dolphins.

If the cold weather isn’t sitting right with your spirt, and you’re ready for some sunshine, here are 13 things to remember when visiting Anguilla.

1. It Has An Interesting History

Photo by Steve Adams

According to Wimco, Anguilla’s first inhabitants came from South America “approximately 3,500 years ago.”

The island’s earliest name was Malliouhana, an Arawak name meaning arrow-headed sea serpent.

When the Europeans invaded, they renamed it Anguilla, a species of eel, because of the island’s long shape.

For years, the British and the French fought over Anguilla, and it remains a British territory to this day.





2. You Can Have Fun Here, But The Subdued Kind

Photo by Polina Tankilevitch

If Anguilla attended a Caribbean party, she would likely sit in the corner sipping her first and only cocktail, while other islands swung from the chandeliers all night. It’s not that she’s judgmental, she’s just reserved.

This isn’t to say that you can’t have a good time in Anguilla. But if you want to run amok, other islands would be more suitable.

Children can make sandcastles and splash in the sea, while parents and grandparents watch on, rum punch in hand.

Teenagers and young adults might enjoy tennis, horseback riding, or stand up paddleboarding, a real test of balance.

There are also spots for live music, as well as festivals and events throughout the year.

3. It's Ideal For Self Care

Photo By Ezekixl Akinnewu

Anguilla is synonymous with wellness. Blue skies, sunshine and balmy sea breezes create an ideal environment for just that, though the pitter-patter of rainfall can also be cathartic.

A masseuse can ease your tension with healing hands. Looking to host a yoga retreat or hire an instructor to lead practice on the sugary sands? Both are possible.

Resorts offer spa services, including salt scrubs, manicures, pedicures, various aromatherapy treatments and more. Imagine being able to enjoy all of that with Shoal Bay as your backdrop. Bliss.


4. There Are Different Ways To Get There

Photo by Spencer Jones

You can access Anguilla the following ways:

By air: According to the Anguilla Tourist Board, the three main gateways for access by air are St. Martin, Antigua and Puerto Rico. The island is serviced by Clayton J. Lloyd, a small international airport.

By sea: Take a ferry from the port at Marigot, on the French side of St. Martin. The trip is beautiful and only lasts about 30 minutes.

You can also book a ferry from the Dutch side of St. Martin, across from Princess Juliana Airport. The cost is around $65 per person, one way.

When taking the ferry in either direction, be sure to check the schedule, so you don’t get stranded, and have your passport handy.

It’s also possible to arrive at Anguilla by private boat, but there are a customs and immigration process involved, which you can read about here.



5. The Weather Is Mostly Pleasant

Photo Courtesy of Planet Ware

US News suggests May through August as the best time to visit Anguilla. This way, you can avoid the hurricane season, which “generally runs from June until October.”

According to the Anguilla Tourist Board, there are 35 inches of rainfall per year (rainy season is between September and October). February and March are the dry months.



6. Don't Be Put Off By It's Small Size

Photo Courtesy Of The Luxury Charter Group

Anguilla may be small, but there are so many beaches, restaurants, and some of the best golfing opportunities in the Caribbean.

If you’re looking for more shopping options beyond Anguilla, St. Martin might be your best bet.

On the French side, Marigot has the chic-boutiques recalling Paris or the French Riviera, while Philipsburg on the Dutch side has jewelry, electronics, clothes and perfume. All of it is duty free.

If you specifically want a high-end shopping experience, nearby St. Barts has enough Cartier, Dolce & Gabbana and Bulgari to scratch that itch.



7. It's A Foodie's Paradise

Photo by David Lansing

Anguilla is the culinary capital of the Caribbean, offering casual and fine dining options.

If you’re staying in a private villa, be sure to let your chef know of any dietary restrictions. He or she will have the skill to make sure that you have a memorable culinary experience.

Blanchards Restaurant (there’s also a shack of the same name) on Meads Bay Beach has great fish dishes.

For some on point meat, there’s Ken’s BBQ, known for its delicious ribs. Want to dress up for a seafood dinner? Head to Mango’s Seaside Grill.

If you’re staying at a high-end resort like the Four Seasons or Cap Juluca, expect the food to be top of the line and eclectic.


8. It Has A Lot Of Beaches For A Small Island

Photo By Camille Minouflet

So, there are thirty-three beaches. Great. But which one is the best?

Most will say Shoal Bay, and with good reason. There are clear, gentle waters, the sand is like sugar, and you might spot a dolphin or two.

It’s the kind of beach that doesn’t require any Photoshop edits because it’s naturally stunning.

Take pictures for your Instagram, and they’ll be sure to earn some likes.



9. It's A Paradise For Lovers

Photo by Sergio Capuzzimati

Grab your honey for a restorative Caribbean getaway that will only serve to bring you closer together.

If you’re staying at an upscale villa or luxury resort, you might decide to simply lounge on a beach chair with a rum punch and call it a day.

But if you do venture beyond, you can enjoy long walks on the beach, horseback riding, scuba diving or a ride on a glass bottom boat.


10. The People Are Friendly And Proud

Photo by Juan Mendez

You will be touched by the hospitality of the Anguillans, who take pleasure in sharing their island with visitors.

They are proud of their varied heritage; a mix of African, Welsh, English and Irish, as well as their rich, layered history.

Anguilla has produced stars in several fields, such as sports, music and the culinary arts.

11. Its Flag Has Changed Over The Years

Photo Courtesy of Flag World

According to the government website, “until  1967, the only flag flown in Anguilla was the Union Jack of Great Britain. The 1967 revolution prompted the introduction of another flag, featuring two mermaids with a shell between them.”

This flag was replaced by the Three Dolphins flag, which is flown by some people today. “The dolphins are orange to represent endurance, unity and strength, and they are in a circle for continuity.”

The present flag combines the Union Jack and the dolphins.



12. Like Boat Racing? Check Out The Anguilla Regatta

Photo by Sarah Richter

The Anguilla Regatta takes place in May. It got its start in 2002 and lasts three days.

While there is a competitive air, it isn’t at the expense of joy and camaraderie.

According to the Anguilla Tourist Board, “all proceeds from the Regatta fund the Anguilla Sailing Association,” which teaches local children how to sail.






13. There's A Variety of Wildlife

Photo by Tom Fisk

According to Lonely Planet, there are 160 species of bird, including the Antillean crested hummingbird and black-necked stilt.

The Hawksbill is an endangered sea turtle. If you happen to see them hatching and making their way to the sea, be sure not to touch them or impede their path.

Keep an eye out for geckos, lizards, iguanas and curious dolphins. And be sure to bring repellent for the creature we all hate: mosquitoes.