Four Seasons Anguilla: Stay, Dine, Play!

For years I had been dreaming of visiting Anguilla – and I am SO EXCITED I finally had the chance to go. My only regret now was not prioritizing a visit sooner. 

I think we all know by now that Four Seasons Bora Bora is my favorite resort in the world (currently) and I would go back every year if I could. However, the Four Seasons Anguilla definitely is sitting in my top three resorts, and because of it’s location closer to my home, I am definitely already planning my visit back. 

Thinking about those words, to me it is like giving a restaurant a Michelin star. I am very selective in where I work and where I vacation. I am always looking for the next thing to move into the top – and so here we are. 

Four Seasons Anguilla – you have outdone yourself. 

If you are truly after a luxury vacation complete with the most stunning beaches, culinary delights (Anguilla has been hailed the culinary capital of the Caribbean) and the most friendly locals, run – do not walk, and book this resort. When I find something I love – I never stop talking about it. 

So I am telling you right now – you are never going to hear me stop taking about this property or visiting, because it’s JUST THAT AMAZING. 

four seasons Anguilla

Four Seasons Anguilla 

Know before you go

First and most importantly, the Four Seasons Anguilla is not open year round. They close in August after Carnival and reopen sometime in October. This is the off season and you will find most resorts on the islands are closed and some restaurants as well. 

I just want to let you know up front so that if you are trying to visit immediately after seeing my videos and this post, it will have to wait. The resort closed the day after I left. 

High season starts mid December and goes through Mid April. You will not find many deals during this time due to high occupancy, but outside of these months you would have a better chance. 

Second, if you are trying to visit during the holiday season (Christmas, New Years), I don’t know how early you have to reserve this but a couple months ago I tried to book and it was already sold out – and now I can see why. Absolute paradise. 

Anguilla is part of the British overseas territories, so it belongs to England, but they do have their own laws.

  • English is the widely spoken language on the island
  • US dollars is accepted pretty much everywhere, so you do not need to change currency if you do not want to
  • Wall outlets use type A and B – which is the same as USA plugs. You do not need a converter
  • Download the free Four Seasons APP and get started planning your trip even before arrival

Getting to Anguilla 

This was by far the one thing that held me back from visiting for so long because it felt complicated. But I did the leg work to see and it actually was really easy!

There are a few ways to get to Anguilla and I am going to walk you through them all to help you make the best decision for your trip. 

The easiest way, in my opinion, is the fly direct. This will come with some caveats though and require planning. American Airlines has two flights per week to Anguilla, on Wednesday and on Saturday. Wherever you are starting from, this flight will connect in Miami. With such limited service, you will need to book in advance and decide if your trip is going to be 3,4 or even week or longer trip. Just keep in mind the very limited availability for this flight from the USA. 

In my opinion, the second easiest way would be to fly into St Maarten (SXM) and fly to Anguilla, which is the shortest international flight in the world at about 8 minutes flying time. The benefit to going this route is that when you get off your flight in St Maarten, you can go right to your flight to Anguilla and the flight is less than 10 minutes. 

The last option, and the option I chose just to see how it would go, would be to book a boat ride to Anguilla from St. Maarten. I did opt to take the easier route and arranged with Four Seasons a shared boat transfer to the island. 

Here is what that process looked like:

  • Arrive in St Maarten
  • Go through customs and immigration
  • Get luggage if you checked any 
  • Meet with the Four Seasons representative after exiting airport
  • Ride to the private boat terminal
  • Check in
  • Before you can get on the boat, you need to clear St Maarten immigration again
  • Boat ride is about 30 minutes – water was very choppy going to the island and if you are prone to sea sickness, I would maybe skip this
  • Once you get to Anguilla, you will walk down the boat way and you will need to clear immigration there, should be quick. 
  • I arrange a car pick up through the Four Seasons with concierge before arrival and someone was waiting for me – the ride was about 10 minutes

All in all, I have three stamps from St Maarten and one stamp from Anguilla by going the boat route. 

You can also catch a taxi over to the French side of the island to Marigot and take the public ferry to Anguilla. 

Four Seasons Anguilla – The Resort 

One thing I noticed about this property was how stunning it is. Beautifully manicured lawns, pools and endless stretches of beaches. It’s so hard for me to eloquently tell you how I feel about this resort because it really was just unforgettable. 

Upon arrival to the resort, when you check in you will be greeted with cool towels and a drink (rum optional). The rum was delicious – so highly recommend. Check-in went very smoothly!

Looking at a map of the property, it looks very big. If you are not staying in the villas, you will be in the resort area and everything is easily walkable. In fact, even if you are staying in a villa, you can easily walk the property. The property isn’t overwhelmingly big but big enough that it feels private. 

I would recommend trying the different restaurants, pools and both beaches while on site. Everything has something different to offer and you never know what spot might become your favorite on your trip. P.S. Look out for the chairs with the faces!



The Four Seasons Anguilla has about 181 room categories that can be occupied for guests. Whether you want a regular guest room or all the way up to a five bedroom beach front villa – there are many options to accommodate your party.

During my stay, I checked into a four bedroom oceanfront villa. Villa number 12 to be exact and there is a door right on the side of the villa that had a one minute walk to the beach (Barnes Bay) and also next to Half Shell Raw Bar (but I never heard anyone during my stay on the beach or at the bar). 

four seasons Anguilla

I first want to say that this villa is unbelievable! I am over the moon I got to experience this and honestly, if I had more time on site, I probably would have stayed at the villa more and brought friends or family. 

four seasons Anguilla

These villas really have everything and come in just over 6,600 square feet! Here is a quick rundown of what was inside:

  • Four bedrooms, two of which are master bedrooms
  • 4.5 marble bathrooms 
  • Indoor and outdoor dining tables
  • living room
  • Infinity edge pool
  • Hot tub
  • A lot of seating set ups outside
  • Gourmet kitchen with every appliance and dish you could think of 
  • Washer and dryer 
  • Outdoor grilling station
  • Residential Assistant to help with all your needs while staying in the villas
  • Golf cart to get around the property

Outdoor Shower

Indoor Dining

Living Room

Infinity Edge Pool and Outdoor Dining

Villa 12 was beautifully decorated with minimal touches, a lot of natural sunlight and entry and exit points all around the villa for easy access (which is great when you are traveling with large groups and some have different sleeping schedules).

four seasons Anguilla

11 people, including 8 children, can be accommodated in this room category. The villa is extremely big, so it will never feel crowded, especially with everything there is to do on site. 

If I have never said it before, I am saying it now – Four Seasons has the BEST beds. There is no bed I have ever slept in that has been cozier. 

Master Bedroom

Master Bedroom

One of the nice touches that I love about staying in the villas is that with the gourmet kitchen, you can get groceries delivered and cook or you can hire a chef to come in and cook for your group.

In addition – no details were missed. I noticed not only was there a Nespresso coffee maker, but also a Keurig and a regular coffee pot. A detail like this means everything to a coffee drinker with a preference, and people do have preferences (I love Nespresso, my mom LOVE regular coffee pot coffee and hates Nespresso). 

You can watch the sunset at the Sunset Pool and Lounge OR if you are staying in a villa – do it here!


The resort offers four restaurants and in-room dining on site. 

The main restaurant, SALT, is where breakfast is served daily, a BBQ Brunch on Sunday’s and dinner. I highly recommend getting a reservation for dinner as soon as you know you are visiting and aim to go before sunset as it is open air and the view is amazing!

During my stay, I diner for both breakfast and dinner. The breakfast menu has a variety of options to please everyone and dinner was more seafood focused, but had something for every taste.

Served with dinner is a local dish called “Johnny Cakes.” This bread is served with butter and hummus on the side and then tableside, a special salt with basil is made to put on top. Nut just a little as it is strong. Eat these as often as you can – so delicious!

One of the gracious staff recommended the “Signature Salt Ceviche” with dinner and I am so glad he did because it was fantastic. I got this as my entrée and then I got the plantains with goat cheese. Unreal. 5 stars all around on the dining. 

I want to preface this by saying I do not love eggs benedict. It’s the hollandaise that I don’t particularly love – however, there was a pulled pork eggs benedict on Johnny cakes with a lemon hollandaise on the menu and I could not say no. Surprise – one of the best breakfasts I have ever had. Do not skip this. 

The Sunset Lounge is right next to the adults-only pool and starts serving food at 11:30am and goes until 11:00pm. I didn’t get the chance to dine here but looking at the menu, it is light bites, sushi, amazing cocktails, and it is open air with views of Barnes Bay!

There are two beach bars with dining: Half Shell Raw Bar, which is overlooking Barnes Bay and where the oceanfront villas are and then there is also Bamboo Bar and Grill next to the Bamboo Pool which has views of Meads Bay!

I only had the chance to dine at Half Shell Raw Bar – but if I can bestow anything from this trip onto you – make sure and order the cocktail “Dean Supreme “Moringa.”” The cocktail tasted more like a delicious smoothie than a cocktail but watch out for those – they can creep up fast. 

There were also tacos available that were not on the menu. I did a trio of tacos: steak, chicken, and pulled pork – all excellent and had a kick of spice. 

Room Service – the menu is pretty robust throughout the day. Since I had stayed in a villa that had a massive pool, I wanted to utilize it more than the public space pools, so I opted to have a late lunch/early dinner one night. 

I ordered the guacamole and a quinoa salad. On the surface these seem like two easy dishes – but Four Seasons never misses. The perfectly thin cut chips with a hint of lime and salt, chefs kiss. And the salad – I wasn’t sure I would love all the ingredients together but they paired perfectly. 


Anguilla is probably the most beautiful island in the Caribbean I have experienced, and that is saying a lot because I get around. I love that the island is small and easy to get around.

There are 33 beaches on the island – and even if you can’t visit them all, I think you will be impressed just with the two located on the Four Seasons Anguilla property: Mead’s Bay and Barnes Bay. 

Meads Bay was my favorite! The most beautiful clear blue waters gracing the sand – you could easily spend a day here and never get tired of the view. 

The Sea Centre is at Meads Bay and you can get snorkeling equipment, paddleboards, kayaks (single and double available), wind surfers, Hobie Cats, and so much more! These are complimentary but on a first come, first serve basis – so plan ahead for this. 

Barnes Bay is a bit rockier, but had some good snorkeling. You can also see little sand areas where you could just have the space to yourself. 

If you are the “activity guy” on your vacation, rest assured, there is more than the beach on site. The sports pavilion offers tennis, basketball, rock climbing, badminton, and more!

There is also a bevy options to be arranged like kite surfing, renting a boat for a day (private or shared) to see different areas around the island, go snorkeling. beach hop, etc. Just contact concierge ahead of your arrival or when you do arrive to set this up. 

*Pro tip – if you download the Four Seasons App (which is completely free), your reservation can be linked and you can chat with someone at the resort prior to your visit, during and even after. But if you are visiting during high season, I would highly recommend booking any type of tour that requires a reservation in advance so you know you have a spot. 

On site, the property has three pools for guests: Sunset Pool, Aleta Pool and Bamboo Pool. 

The Sunset Pool is the adults only pool and it is a salt water, infinity edge pool – complete with loungers and the Lounge in eye site. This pool overlooks Barnes Bay and you can often see very vibrant sunsets at night from here, hence the name.

The Aleta Pool is sexy! Lush cabanas, beautiful Caribbean Blue views, plenty of room in the pool to drink with your people, or even a lazy day in a lounger or cabana. 

The Bamboo Pool is the family friendly pool and in my opinion, is in the best location as it is mere steps from Meads Bay! You can easily go between the two.

If you are looking to get a massage, there is a spa on site with a wide variety of treatment options. The spa overlooks the blue waters and has its own pool in the outside relaxation area. One thing I think you will love about this spa is that you can get a seaside treatment outside in one of the cabanas if you like and you can even arrange to have a massage done in your room or villa. The choice is yours. 


Looking for a workout? There is a gym on site and classes are offered. You will need to check what is available during your stay. 

Family Friendly

A lot of you ask about families being on site and activities for kids. I do not have kids BUT – I walked the entire property and there was families there.

I also found a kids club ..

Little kid loungers at the Bamboo Pool..

And the Bamboo Pool is family friendly!

How I booked My Stay

You all know how much I LOVE a deal or a travel hack, so here is how this all came to be. 

First, I have the APP. I opened it and saw they were randomly offering a deal on last minute bookings up to 5 nights in length. This deal was only available on the app. 

The deal was, they would match up to five nights in stamps. The way works is, if you pay and stay 10 nights in any combination of stays, you will then get a free night on your next booking that will be equal to the average cost of the 10 previous booked nights. 

All that being said, I booked two nights in the lowest level room category which was a studio king room. The value of each stamp is worth $822.50 and now I have four of them, getting me two nights closer to a free stay. 

Second, I booked with my Chase Sapphire Reserve and was able to get 3 X points on travel bookings. 

The real deal was on arrival and this is a hack I use whenever I travel most places. I looked at the resort availability before ever booking and saw every room category was available. I knew I would be able to upgrade to some room category higher than what I paid for initially upon arrival at a substantial discount. 

I had my eyes set on one of the four bedroom villas but they were selling for about $8000+ per night and I did not want to pay that. Upon arrival I was able to upgrade for $2000 per night. Now if I had more guests with me, this would have been great. 

* I want to say not to count on this as an option because you never know when the resort will be sold out. This is never a guarantee!


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