Experience the island by exploring Anguilla’s heritage and culture

The island of Anguilla is more than just a pretty face. Beyond the beautiful beaches, travelers can make a connection with the essence of the island and explore what makes Anguilla unique. Converse with locals, explore unexpected spots that aren't on your itinerary, and savor every memory.

Where does one start to scratch beneath Anguilla's pristine surface? There's no exact science as to how to make your Anguilla connection. We can begin by exploring the island's long and storied history, people, culture, food, drink, traditions, businesses, and favorite diversions.

Anguilla: How it all got started

As gorgeous as Anguilla's 33 beaches are, you would think you'd be elbow-to-elbow with tourists. Part of what makes Anguilla so appealing is the ability to step out on a beach and discover that you are enjoying this exquisite moment all by your lonesome.

When considering the appeal of Anguilla's modern-day solitude, it's possible to comprehend the Arawak Indians arriving from South America and realizing this place was something special. The Arawaks called the island Malliouhana, their word for serpent, describing Anguilla's thin, eel-like shape. It wasn't until 1650 that the British arrived and colonized Anguilla.

Next, there was a period in which Anguilla was caught in a power struggle between Great Britain and France. After Britain gained control, Anguilla was placed under the administrative authority of St. Kitts. Finally, in 1980, Anguilla officially separated from St. Kitts, and the island has since thrived as a British overseas territory.

Anguilla's best history and wildlife tours

Anguilla is lucky enough to have an organization that preserves the island's past. The Anguilla National Trust is the voice for Anguilla's national heritage. Their tours offer visitors the chance to explore 1000-year-old petroglyphs carved into the rock walls at Big Springs and visit the Wallblake Plantation House, which dates back to 1787 and has witnessed much of the island nation's history.

Through the Trust, outdoor-minded vacationers can even go on a Turtle Patrol to observe the nesting sea turtles at 15 different beaches. Birders will leap at the Sombrero Island Tour, which offers a chance to spot rare native birds and reptiles.

If you're looking to stay at a tropical resort that is drenched in history, consider Carimar Beach Club on Meads Bay. This landmark hotel opened in 1985 and offers one and two-bedroom suites. The staff at Carimar graciously share island history at their oceanfront setting.

Anguilla's favorite food

Food can bridge generations with recipes and traditions handed down over the years. The one food that captures Anguilla's essence and heritage for many would have to be Johnny cakes.

This biscuit or flatbread comprised of flour, cornmeal, and baking powder is a wonder that goes with anything and everything: Breakfast, lobster, ribs, chicken, even shrimp. You can find it on the menus at Palm Grove Bar and Grill, Tasty's, and Veya's.

A rum lover's paradise

Rum is the spirit of choice in the Caribbean. That is certainly the case at Elvis' Beach Bar on Sandy Ground.

Since 2007, customers have flocked to the bar for Elvis's famous Rum Punch. Behind his rustic bar crafted from an Anguillian racing boat, Elvis pours a delicious concoction of rum, orange and guava juice, amaretto, and fresh nutmeg.

Elvis also designed the menu at Anguilla Great House’s Coconuts beachfront bar, so those who can’t get enough of his flavors can enjoy authentic drinks on Rendezvous Bay.

For vacationers who desire rum in a more upscale setting, travel to Shoal Bay Beach and the Rhum Room at Zemi Beach House Resort. Choose from over 90 rums originating from Antigua, Barbados, Bermuda, Columbia, Dominican Republic, Guadeloupe, Guyana, Haiti, Jamaica, Martinique, Peru, Trinidad, and Venezuela.

The music men of Anguilla

If music is the soundtrack to Anguillian life, then Bankie Banks Dune Preserve on Rendezvous Bay is a cornerstone. Banks, who has performed with artists such as Bob Dylan and Jimmy Buffett, oversees his operation while serving savory barbecue, cold drinks, and outstanding live music.

Banks is also the founder of Moonsplash, the Caribbean's longest-running music festival. Reggae acts from around the globe travel to perform on the island.

Michael "Dumpa" Martin is another Anguillian whose Steel Pan music has impacted generations. Martin's Pan Fusion band showcases a mix of soca, calypso, and jazz that regularly plays at school and community events on the island.

Boating: Anguilla's national pastime

One way to get an Anguillian fired up is to ask who will win the Anguilla Day Boat Race, which takes place each year on May 30th. Nearly the whole island shuts down to either participate or watch this national event.

Boatbuilding, boat racing, and the sheer joy of sailing have deep roots in Anguilla. The boat races begin around Easter and then build to a frenzy during Anguilla Day on May 30th and the Anguilla Summer Festival, occurring throughout the first week of August.

A boat tour or charter is a great way for vacationers to feel Anguilla's sporting passion, as well as explore its 37 miles of coastline. Boat captains share Anguilla's geography, history, and culture during leisurely tours to neighboring Dog Island, Prickly Pear, Sandy Island, Little Bay, and Scrub Island. It's the perfect way to appreciate Anguilla's beauty and rich culture, all at the same time.