Powdery smooth white sand. Crystal turquoise waters. Swaying palm trees. How could there be anything wrong with this island? What could possibly inspire me to write a post about bad things in nirvana? You will see.
My good friend Micki (from The Barefoot Nomad) and I first met in the Caribbean. Who would have thought 3 years later we would “ditch” our families, fly nearly 30 hours and return to the Caribbean?
When I received an invitation to discover the tropical paradise of Anguilla after several cold months in Canada, not even the long flight could deter me from a few days in the tropical sun.
Could a 30-hour journey via Kelowna, Vancouver, Phoenix, Charlotte and St Maarten really be worth it for 3 days in Anguilla?
Turns out it was.
Our arrival into Sint Maarten via the famous so-low-you-can-almost-touch-the-plane Maho Beach was spectacular, but not as much fun as the 20-minute ferry ride to Anguilla.
After 3 days on this dreamlike paradise I discovered 5 things that I knew I had to warn you about to make sure you had the best possible time in Anguilla.
Do not go to Anguilla and make these 5 mistakes:
1. Miss Sandy Island
My favourite moment of the trip. And not one to miss. We spent the morning snorkelling around the edges of Anguilla on a small charter boat before pulling onto Sandy Island.
The aquamarine sea gently lapped on the white sand, warmly beckoning. It was an easy decision to jump off the boat and explore this small island.
Sandy Island is a tiny cay 2.9 miles northwest of the main island of Anguilla. You can catch a short boat “shuttle” from the small pier at Sandy Ground Beach.
“Happiness” costs US$10 per person round trip.
Unlike most isolated islands I have visited, Sandy Island has been only one that provided fresh, delicious food. There is just one restaurant on the island, where food is prepared fresh and hot for you to enjoy.
And of course, it wouldn’t be a tropical paradise without a cocktail in hand, relaxing in a hammock on the beach.
2. Forget Your Sunglasses
You may have noticed on my Snapchat feed plenty of squinty-eyed photos and videos. After getting used to the -6°C (21°F) temperatures in Canada and being awake before sunrise, it didn’t even click to bring sunglasses with me.
The island is fairly small and shopping options are limited. So finding sunglasses was near impossible. Most locals do their shopping in Puerto Rico or online.
So for 3 days I squinted at the rays and cursed my forgetfulness.
The only time it rained was a quick 5-minute downpour and then we were back to sunshine.
3. Spend Every Day On The Beach
It’s tempting to spend most of your time at the beach in Anguilla. After all, this is the Caribbean. The waters are warm, calm and tantalisingly translucent. The soft sand is a dazzling white and the temperature is always perfect.
However Anguilla has more to offer than just the beach. From its 17th century churches to a smallheritage museum, the culture buff will find something to see.
Or perhaps history is not your thing, but pools are. Skip the beach and make a b-line to one of the luxury hotels for a day at the pool. For a small fee you can experience an indulgent day at theViceroy’s infinity pool, sipping cocktails and soaking up the sea views.
4. Skimp Money On A Hotel
As you can imagine Anguilla is home to an array of upmarket hotels, so choosing one is going to be tough. 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.
The island has it’s own classification for budget accommodation, where a budget-friendly option will set you back about US$150 per night. My first few nights were spent at Anguilla Great House Beach Resort, which has an amazing location, directly on the beach, but the rooms could have used a renovation. If you are looking for more of a rustic, modest room then this is your choice.
I also spent a night at Anacaona Boutique Resort. This one is not on the beach, but does have access to two beautiful pools. Beware the resident roosters though, as a light sleeper, they kept me awake most the night.
Based on my accommodation experience on Anguilla, I’d suggest you don’t skimp on your accommodation. Enjoy every minute of your well-deserved vacation!
5. Be On A Diet
Anguilla is not the place to be on a diet. This is one of the worst things you can do on a Caribbean island getaway. The food is excellent, which was far removed from my time in Ambergris Caye, Belize. In Anguilla the typical Caribbean cuisine staples are beans, rice and plenty of fresh seafood. And on that note…
Here are my 5 favourite places to eat in Anguilla:
1. Sandy Island Restaurant
You can’t get any better than eating on your own private island. This island is a short speedboat shuttle from the main island of Anguilla. The food is fresh and surprisingly good. It is all prepared on the island and not carted over from the mainland. My chicken and salad plate was delicious. It could have been the spellbinding views, it could have been really good food, but honestly, how can a meal be bad when you are eating on your own mini-island in the Caribbean?
2. Veya
The place to be in the evening. When we arrived there was live music, dramatic décor and friendly staff. But most importantly, impeccable food from a New Yorker.
3. Straw Hat
Maybe it’s just me, but I love a restaurant with a difference and the Straw Hat really goes all out with its themed name. Straw-hat lights, bread served in a straw hat and an even an opportunity to walk out with your own straw hat. Situated right on the ocean this place serves delicious food in a fun, vibrant atmosphere.
4. Smokey’s
Another restaurant situated right on the beach and the perfect place for lunch. Grab a table on the sand, dig your toes in and enjoy the views. Perfect for families as the kids will be so engrossed with playing in the waves or building sandcastles you can enjoy your cocktail in peace. My jerk chicken wrap was spicy, but don’t miss the fish bite appetiser!
5. Mango’s
Fine dining on the beach. You won’t get your feet in the sand, so it’s the best opportunity to dress up and head out with someone special or friends. While it wasn’t the best steak in my life, it was still a solid contender.
As with most Caribbean islands, you have to be prepared to spend a pretty penny to enjoy these dining experiences. The food is not cheap, but it is fresh and you can always save money on attractions. After all, whittling away your days swimming in the alluring warm waters of the Caribbean is totally free.
The Bottom Line
When my biggest complaints involve sunglasses, choosing a pool or beach and dodging my diet, it’s hard to taint the solid reputation Anguilla has earned as an upmarket relaxing Caribbean getaway. Next time I’ll be ready – and might even bring an extra pair of sunglasses just to be safe.
Hello, my name is Jack Sparrow. I'm a 50 year old self-employed Pirate from the Caribbean. 
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