4 Types of People You Will Encounter when you visit Anguilla

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We talk all the time about the authenticity of the relationships you experience on a visit to Anguilla.


The kindness, the warmth, the helpfulness and the all around love that each and every visitor to the island can’t get enough of. If you have ever visited, you know what we are talking about. And if you haven’t, you’ll soon find out.

What’s really interesting about this aspect of our little island paradise is the diversity of the people you meet here.

We’ve assessed the diverse personalities available to connect with, and we worked hardddd to narrow the list right down.
Here are the four people you are sure to encounter on your visit to Anguilla.

The Artist

Go ahead, ask anybody that has visited the island and they will tell you that our music scene is ahhh-muhhhh-ziiiiiing!
Live Acoustic Music, Jazz Bands, Soca, Folk, Pop, R&B and of course Reggae, there is no shortage of opportunities to get that good vibe. Local artists are a part of the fibre of Anguillian life. They tell stories that bridge our past and present. Their music has connected Anguilla and Anguillians to most corners of the earth.


Aside from musical artists, there are writers, poets, designers, photographers, film-makers and fine artists who add their creative flair to life on the island.


When you visit Anguilla I can guarantee you’ll have at least one meaningful conversation with a creative whose finding inspiration in paradise. Hey, you just might consider joining them 🙂

The Student

Anguilla is home to the St. James School of Medicine, which hosts a number of foreign and some local medical students pursuing their degree. Students of the Medical School have integrated themselves into Anguilla’s culture, day and night life. It’s not uncommon to bump into a Medical student at a local bar, restaurant or event; yes, even future doctors have a good time. 🙂


Locals that are International Students visit Anguilla when on break from University in the United States and the United Kingdom. They are “home” predominantly during the summer and winter months for Carnival and Christmas respectively.

The Expatriate

….or Expats, as we sometimes call them, are the foreign born men and women who have chosen to make Anguilla their home. Expatriates range from retirees to restauranteurs and businessmen and women on the island. They are usually past visitors to the island, like you, that fell so deeply in love they chose to move here. 🙂


Meeting an expatriate when you are on the island is a forgone conclusion. Chat about life in the developed world, and hear all of the reasons why moving to Anguilla should be step 1 on your retirement plan.

The Facilitator

Pretty much anybody you meet will help you out if you’re in a jam. They’ll stop you if you are driving on the wrong side of the road, spend a few minutes giving directions and offer up little nuggets of advice that’ll prove valuable during your stay.


But they are not The Facilitator. What we are referring to here are those special people that go out of their way to curate the different aspects of your experience. Driving on the wrong side of the road? Not a problem, a Facilitator will stop you, instruct on the correct driving rules and ESCORT YOU to your location. They will talk to the hostess at the restaurant to ensure they keep an eye on you when you leave, and they will follow up after the fact to ensure “the guest”, that’s you by the way, got home safely.


The facilitator will hear you discussing what to do for drinks this evening and take you to their favourite spot. They’ll buy you a round, destroy you preconceived itinerary, and plot every aspect of the rest of your vacation, keying you into all of the local spaces “ya going like a lot”.


The facilitator adds you on facebook and likes all your photos, tagging you in epic sunsets and grilled lobster pictures, long after you’re gone. This is the guy you end up inviting to your birthday celebration in Montauk, and he’s the reason why you come back to Anguilla year after year. To connect, to catch up, to create new memories.

Most people visit Anguilla to unwind, to disconnect and then reconnect with themselves and (at the risk of sounding super corny) the Universe. Yet, when you vacation in Anguilla, it is assured you will form new bonds with people from all walks of life who invariably improve the quality of your experiences on island and in many cases shape some of your perspective on life. 

On the island we hail our people as our greatest asset, more vital to the visitor experience than the beaches, the food and the adventures combined. We celebrate all Anguillians. Anguillians by birth, and those who have made Anguilla their home by choice.

Traveller Health Requirements


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