Four Seasons Anguilla Trip 

We spent 5 nights at the Four Seasons Anguilla and had an amazing time! Here are all the details from our trip including how to get there, the highlights of the resort, and tips for travelers! 

Four Seasons Anguilla: Our Trip Recap!

If you follow my stories and Reels on Instagram, you saw that we spent 5 days in the Caribbean for Thomas’s 40th birthday last week. (Be sure to check out the video highlight reel!) 

Our destination was the Four Seasons Anguilla, and it was absolutely amazing! Rather than recap our trip day by day, I’m sharing topic by topic so future travelers can get a great overview.

Dress rented from Nuuly!

How we chose Four Seasons Anguilla

This trip actually starts with Beautycounter! In 2021 the company had a year-long challenge where consultants could earn points towards a prize. The prize that I earned was a $2500 gift card to the Four Seasons. 

I started to look into properties to visit, and ruled out the $2500 a night Miami property pretty quickly. There are a few Caribbean properties, including the Bahamas, Nevis, and Anguilla. The Four Seasons Anguilla had the perfect balance of tropical and posh, so we chose it for our trip! 

Using Credit Card Points To Book The Flights and Room

So we ultimately book all 5 nights on points and saved our gift card to use on all of our food, drink, and hotel charges. EPIC!!! 

If you want to learn more about travel rewards, read this post. I’ll also be sending out an email in a few days with the exact cards, amounts of points, and how we booked this trip to my travel email list, and you can opt in here to get that email.

Traveling To Anguilla

Flying Into St. Maarten

We flew from Charlottesville to Atlanta and Atlanta to St. Maarten. It was a bit of a schlep.

When I researched the trip, though, the reviews said most people fly to St. Maarten and take a ferry to Anguilla.

Once we landed in St. Maarten, we had take a bus from the plane a very short ride and then wait in a long line for customs (about 20 minutes), then we met a Four Seasons greeter who took us to the ferry dock. 

TIP ON TIPS

Anticipating tipping, I went to the bank and got a bunch of $5 and $10 bills. We BLEW through them there were so many different points of tipping. So bring tons of cash and remember to save some for the return trip! 

Funtime Ferry To Anguilla

The whole process of getting to Anguilla reminded me a lot of traveling to Bald Head Island. 

I was able to arrange for the ferry through the Four Seasons concierge. The total cost was $440 round trip (!) but there wasn’t really a better way to do it other than fly directly into Anguilla. Definitely factor this cost into your travel budget. I was able to charge the ferry to our room, which meant we could put it towards our gift card. 

We had to show our passports 5 different times and after waiting in a little open-air area, we finally boarded the boat. 

This was not a big passenger ferry like we we thinking it would be! It was basically a speed boat, which was fun. 

We met our Anguilla BFFs, Brent and John (HI GUYS!), on this boat ride. It bonded us for the week and it was great to have friends to run into! 

The boat ride was about 25 minutes (and quite rocky over the ways!) but it fun because the had beers and rum punch and we were able to relax and watch the islands go by. And we were so close from our travel day ending. 

Arriving in Anguilla

The ferry terminal in Anguilla was small and casual (I think they are rebuilding it). We had to go through Anguilla customs which was quick but more passport showing. Then we were assigned a taxi (more cash!) to the Four Seasons. That taxi ride was about 20 minutes.

I think it probably took about 2 hours from landing in SXM to arriving at the Four Seasons. 

Arriving at the Four Seasons 

FINALLY we were there!! And we were greeting with cool towels, ocean breezes, and welcome rum drinks. 

Our Ocean View Suite 

We had booked an Ocean View Studio, but we were so grateful to be upgraded to a suite!!

Our room was spacious with amazing views of the ocean from the balcony where we had coffee every morning. 

There was a plunge pool on the balcony, which had a heater. But to be honest it was pretty cold even with the heater so we never got in it. We did turn our huge bathtub into a hot tub though! 

We also loved the location of our room in building 32. And we were super close to our favorite spots: SALT (for breakfast and dinner) and the Sunset Lounge and Pool. 

Our room had full-size bottles of shampoo, body wash, and hand soap, which was appreciated (for a waste reduction standpoint too!). 

We also loved the robes and slippers and turn down service. 

Four Seasons Anguilla Pools

The Sunset Pool is the stunning infinity pool with amazing sunset and ocean views. It’s adults only and wasn’t too crowded – we were always able to get a chair. 

There were two other pools – the Bamboo pool and Aleta pool – but since we like a view, we never spent time at those. 

The service at the pools was outstanding, with cushiony chairs, towels, and friendly staff who would bring you anything you needed from rum punch to lunch. 

Nearly every hour they brought by samples of smoothies, drinks, or snacks. And once a team from the spa came around offering complimentary shoulder massages! 

There was also a sunscreen station at every beach and pool, so don’t pack any of your own. 

The Two Beaches

Our favorite beach, Barnes Bay Beach, was the “wilder” of the two. There were rocks with huge crashing waves! 

As the week went on, the beach shrunk. Our friend Yeury said every full moon the tide crashes like this and put a cliff into the sand which means there is less room for chairs.

We spent our first few days down on the beach, we ended our trip up at the Sunset Pool. 

The sand was like walking in snow – you would sink in 6-12” deep! Thus beach walking was very challenging haha. But it felt so cool. 

The ocean was a little too rough for swimming near the resort, but it was much calmer at the end of Meads Bay Beach.

The Four Seasons had snorkel gear and other water sports like paddle boards, but it was much too rough for either of those when we were there. 

Read part II of our trip here: Anguilla Food and Drinks

• All the restaurants, food, and drinks we enjoyed
• Tips for traveling to the Four Seasons Anguilla!