Worst Things To Do In Anguilla

A slice of paradise that’s got it all – powdery smooth white sand, water so crystal clear it’ll leave you mesmerized, and palm trees swaying like they’re doing the island dance.

You might think, how could there be anything wrong with this heavenly place? Well, let me tell you a tale that’ll have you hooked. A tale of adventure, friendship, and a Caribbean island that defied all odds!

Worst Things To Do In Anguilla

It all started with my good friend Micki, from The Barefoot Nomad. Three years back, fate brought us together in the Caribbean, and who would’ve guessed that destiny had another grand plan in store?

Fast forward, and there we were, throwing caution to the wind, leaving our families behind, and embarking on a daring 30-hour journey. An extreme flight with stops in Kelowna, Vancouver, Phoenix, Charlotte, and finally, St Maarten, all for the promise of a few sun-kissed days in Anguilla.

Worst Things To Do In Anguilla - sleepless airport

You might wonder, was it worth the sleepless hours and airport hopping? Could this tropical paradise truly live up to the hype?

Oh, it most certainly did!

Every minute spent in the air was like a ticking countdown to our Caribbean dream. And when we finally set foot on the enchanting island of Anguilla, all the travel weariness melted away like ice in the sun.

So, my fellow adventurers, hold onto your hats and join me on a journey filled with delights and surprises, as I unveil the magic of those unforgettable three days in Anguilla.

From the endless stretches of pristine beaches to the warm embrace of the Caribbean sun, this is a tale that will show you how even a 30-hour voyage is a small price to pay for the sheer bliss that awaits in paradise!

Worst Things To Do In Anguilla - window to anguilla

Where is Anguilla?

In my recent adventure, I was invited by the Anguilla Tourist Board to spend three unforgettable days in Anguilla, a British overseas territory nestled in the Eastern Caribbean, just a short 20-minute ferry ride north from Sint Maarten and to the east of Puerto Rico.

Read our post on 22 Things You May Not Know About Anguilla.

How Do You Get To Anguilla From St Martin?

Our arrival into Sint Maarten via the famous so-low-you-can-almost-touch-the-plane Maho Beach was spectacular, but not nearly as spectacular as the 20-minute ferry ride to Anguilla. What a fun way to start your journey to an island paradise.


What is Anguilla best known for?

Anguilla is a popular tourist destination because of its easygoing atmosphere and magnificent beaches and waters. Make sure to check out Bay Beach & Shoal Bay East.

Where is the best place to stay in Anguilla?

In my experience, if you are spending your vacation on a luxury island like Anguilla, go all out and stay in a luxury hotel, such as the Viceroy or CuisinArt Golf Resort & Spa. If you’re looking for something more budget-friendly, my recommendations are below.


What is Anguilla’s famous dish?

Anguilla’s National Dish is Pigeon Peas and Rice. But they have the freshest seafood ever. You can find my 5 best places to eat here.

Worst Things To Do In Anguilla - Crayfish

What are the best things to do in Anguilla?

Your Caribbean island stay is most likely to revolve around water, sunbaking, and eating.

You’re going to want to make a list of places to visit including Shoal Bay, Rendezvous Bay, Bay East, Shoal Bay East, Island Harbour, Crocus Bay, and Maundays Bay. Just for a start.

Check out these cool activities from Get Your Guide.


Buckle up, because I’ve got some juicy insider secrets to spill after spending three unforgettable days in this dreamy paradise called Anguilla.

Now, don’t get me wrong, this place is pure magic, but there are a few things I just couldn’t keep to myself.

Consider this your ultimate guide to navigating the wonders of Anguilla, ensuring that you have the absolute best time of your life in this tropical haven.

So, get ready for some epic tips and tricks that will take your Anguilla adventure to a whole new level of awesomeness!

Worst Things To Do In Anguilla

5 Worst Things To Do In Anguilla

1. The Worst Thing To In Anguilla – Miss Sandy Island

Let me tell you about the ultimate highlight of my trip – a moment that was pure magic and simply unmissable!

Picture this: we kicked off the day with some epic snorkeling adventures, gliding along the edges of Anguilla on our trusty little charter boat. And then, like a siren’s call, we spotted it – the mystical Sandy Island, floating like a dream in the aquamarine sea. Oh, there was no resisting its allure!

As we pulled up to its pearly shores, the soft waves serenaded us, inviting us to jump ship and explore this tiny cay of wonder.

Worst Things To Do In Anguilla - Sandy Island

Let me tell you, Sandy Island is a true gem, just 2.9 miles northwest of the main island of Anguilla. And guess what? Getting there is a breeze with a short boat “shuttle” from the pier at Sandy Ground Beach. The ticket to “Happiness”? Only US$40 per person for a round trip – a steal for what was about to unfold.

Now, hold your hungry hearts because this is where it gets really exciting! Unlike many isolated islands, Sandy Island greeted us with open arms and a one-of-a-kind treat – fresh, mouth-watering food!

Yup, you heard that right – there’s just one restaurant in this tiny paradise, and they cook up a storm, serving you scrumptious dishes that’ll make your taste buds dance in delight.


And let’s not forget the icing on the cake – a tropical cocktail in hand, swinging lazily in a hammock on the beach. Oh, the sheer bliss! Sandy Island is like a dreamscape where good vibes, great company, and amazing food create the ultimate recipe for an unforgettable day in paradise.

So, my fellow beachgoers, don’t let this experience slip away – it’s a taste of heaven that’ll linger in your heart forever!

Worst Things To Do In Anguilla

2. The Worst Thing To In Anguilla – Forget Your Sunglasses

You probably noticed on my Instagram Stories a lot of squinty-eyed selfies! Can you blame me? After braving the chilly -6°C (21°F) temperatures in Canada and waking up before the sun, the idea of packing sunglasses didn’t even cross my mind. D’oh!

And guess what? The tropical paradise of Anguilla welcomed me with a challenge – shopping options were as scarce as buried treasure on this small island. Can you believe it?

Worst Thing To In Anguilla

Finding shades was like searching for a needle in a haystack. Turns out, the locals have a smart trick up their sleeves – they do their shopping spree in San Juan, Puerto Rico, or online.

So here I was, squinting like a pirate hunting for treasure, and cursing my forgetfulness like a true adventurer!

Worst Things To Do In Anguilla

3. The Worst Thing To In Anguilla – Spend Every Day On The Beach

I get it, the siren call of the Caribbean Sea is too hard to resist. Warm, crystal-clear waters that beckon you to dive right in, soft sand so white it could dazzle the sun and the weather? Always perfect, just like your favorite vacation dreams!

But hey, before you go all-out beach bum mode, let me spill the beans – Anguilla has way more treasures to explore beyond the beach!

Worst Thing To In Anguilla

From enchanting 17th-century churches to a charming heritage museum, Anguilla has got your sightseeing fix sorted. Get ready to immerse yourself in the island’s fascinating history and culture, because trust me, these places will be worth every moment spent away from the beach.

If history isn’t your jam, make a beeline straight to the lap of luxury at one of the island’s fabulous hotels. Say goodbye to the beach for a day and say hello to an indulgent poolside paradise! For a small fee, you can chill like royalty at the Viceroy’s stunning infinity pool. Sip on mouthwatering cocktails, soak in the awe-inspiring sea views, and feel like a king!

Worst Things To Do In Anguilla - hotel

Worst Things To Do In Anguilla - hotel

4. The Worst Thing To In Anguilla – Skimp Money On A Hotel

If you’re setting sail for the paradise of Anguilla, brace yourself for a tough choice – picking the perfect hotel from a treasure trove of upmarket options!

Let me tell you, this island knows how to pamper you like royalty, so when in doubt, just go all out! Embrace the lap of luxury at legendary spots like the Viceroy or the CuisinArt Golf Resort & Spa – trust me, it’s an experience you won’t forget!

But, fear not, for Anguilla also has a treasure chest of budget-friendly accommodation. Picture yourself in a rustic, modest room at the Anguilla Great House Beach Resort, directly on the beach – the location is pure gold!

Sure, the rooms could use a bit of a spruce-up, but for those seeking a more laid-back vibe, this spot might be the treasure you’re looking for.

Worst Things To Do In Anguilla - hotel

I also spent a night at Anacaona Boutique Resort. While not right on the beach, it offers a bounty of beauty with access to two fabulous pools. Beware, though – the resident roosters might serenade you all night long. So, if you’re a light sleeper, consider yourself warned!

Worst Things To Do In Anguilla hotel

But here’s the ultimate booty of advice – don’t skimp on your accommodation! Based on my accommodation experience in Anguilla, I’d suggest you don’t skimp on your accommodation. Enjoy every minute of your well-deserved vacation!


5. The Worst Thing To In Anguilla – Be On A Diet

I’ve got some juicy tales from the Caribbean that’ll make your taste buds dance like never before! Anguilla is the last place you want to be on a diet, trust me! This island’s culinary delights will blow your mind faster than a cannonball off a ship!

Worst Things To Do In Anguilla - food

Let me tell you, this place is a far cry from my time in Ambergris Caye, Belize. In Anguilla, it’s a feast fit for pirates, with Caribbean cuisine staples that’ll make you weak in the knees – beans, rice, and fresh seafood galore! Prepare to dive into a treasure trove of flavors, where every bite is a mouthwatering adventure.

You can read my full culinary adventure here in the 5 best places to eat in Anguilla and let the feasting begin!


When you find yourself fretting over shades, struggling to pick between a pool or a beach, and dodging your diet like a true foodie pirate, you know you’re in for a heck of a good time in Anguilla!

This place is a Caribbean treasure chest of relaxation and luxury, and next time, I’ll be more prepared! I’ll be sure to pack my sunnies like a seasoned explorer because now we know the sun never sets on an epic Anguilla adventure.

So, let’s raise our coconut cocktails to this unforgettable Caribbean escape. Anguilla, you’ve won my heart with your charms, and I’ll return for plenty more poolside paradise memories and sandy beach days. Next time I’ll just pack a few extra pairs of sunglasses – just to be safe!




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