Can’t Take My Eyes Off of You: The Four Seasons Anguilla

Four Seasons Anguilla

At this stage in my life (40s – although I won’t be able to say that for much longer) and my friends’ lives, it is nearly impossible to find a time to get together. Work/kids/spouses/responsibilities/commitments and just life gets in the way and dates never seem to align for the entire group.

Knowing this and being the genius that she is, my dear friend planned a getaway the week after Thanksgiving.

Brilliant, right?!

Everyone has fulfilled their family obligations, kids activities are somewhat manageable, and quite frankly everyone needs a break after the pressures of Thanksgiving.

So off we went to Anguilla and it was glorious.

If you are like me and wondering why you haven’t heard of many people visiting Anguilla, it is because it has historically been challenging to get to (US — San Juan or St. Maarten — Anguilla via boat or puddle jumper).

Good news on that front (and I predict you will hear of a lot more people traveling to Anguilla): In December 2021, American Airlines announced it would be opening up direct flights from Miami to Anguilla (about a 3 hour flight).

We stayed at the Four Seasons – a breathtaking property right on the ocean and a short 10 min ride from the airport. My friend observed that a certain spot on the property was like standing on the bow of a ship — it literally looked right over the beautiful blue water. The food was great, the service was amazing, there are lots of activities to choose from (spa, fitness center, water sports, tennis, shopping, etc. I was also told there is a basketball court which my son would love) and the island is really charming. Great restaurants to choose from both on the property and off.

Highly recommend! This one’s for the Five Seasons! ❤️❤️❤️❤️❤️

Anguilla is TINY — only 16 miles long and 3.5 miles wide; its total population is approximately 15,000. It is also unique due to restrictions imposed on large cruise ships, etc. From U.S. News, “Compared to some Caribbean islands masquerading as tourist traps, you’ll find something a little more authentic on Anguilla. There’s an embargo on large cruise ships, casinos and high-rise hotels, but a surplus of clear, coral-filled waters, unmarked and unpaved roads and low-key beachfront villas.” And because I was curious, Anguilla is “an internally self-governing overseas territory of the United Kingdom.”

Restaurants to try in Anguilla:
JACALA – no website; must have reservations – only 28 seats in the restaurant
BANKIE BANKS’ DUNE PRESERVE: Bar owned by a Reggae singer Bankie Banks
SCILLY CAY – a small island with a restaurant serving Anguillan lobster
DOLCE VITA – also no website; Italian
GARVEY’S BEACH SUNSHINE SHACK – As the name implies, BBQ chicken, ribs, and frozen drinks
MANGO’S SEASIDE GRILL – Seafood restaurant located right on the beach.

**Lucky for you, my friend’s family owned a home in Anguilla for years and these are her list of favorites!
(Four Seasons Guests, Ask the lovely Concierge to make these for you)

And speaking of things I can’t take my eyes off of, I don’t know if you’ve been shopping at MATCHES FASHION lately but if not, you should – there is so much good stuff this season. Get it all here. Spring is coming…get it before it sells out!

Four Seasons Anguilla
The Four Seasons Anguilla is an all white open air maze perched atop the beautiful blue ocean.
Half Shell Beach Bar: our lunch spot on the first day after we landed. Many a margarita and rosé was had.
Bamboo Bar and Grill: our daily lunch spot the rest of the trip.
Another view of Bamboo Bar and Grill
This was our villa – amazing.
A fabulous kitchen although it saw no action other than the occasional corkscrew and coffee maker.
Outdoor showers in the bathrooms.
Our private pool
There are several pools but we opted for the beach every day.
Guacamole Bar
This is a club next door to the Four Seasons.
There are several pools to choose from at The Four Seasons.
If there is a DJ on site you can guarantee we will be close by.
This was where we earned our nickname, “The Five Seasons”.
Right where that man is walking on the right is where my friend observed that it was like standing on the bow of a ship.
The Sunset Lounge was our favorite spot.
Floating Bar.
Fitness Center
There are lots of options for accommodations – villas, condos, etc.
Allow me to introduce you to The Five Seasons pictured at Jacala restaurant.
We had no fun at all.
Or maybe we did.
We actually had the best time ever. And how cute is this crew???
To your left, our Anguillan Hostess with the Mostest
Hope we get to go back. It was a dream!

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