The traveler I am today has come a long way from the person that began this blog 10 years ago. Experience does that, it changes you slowly. I have a better appreciation of what happens not only front and center at a hotel, but also what has to happen behind the scenes and the little details in service and amenities that make one hotel miles ahead of another. I also have great respect for every dime that a guest spends when they travel; most people look forward to their trips for half the year if not all of it. Most people also save to make these trips a  reality, so every dime they spend has to be well worth it.

So when I visit hotels now, especially in the context of sharing with you guys here, on Instagram, on TripAdvisor, I try to make sure that I’m capturing and thinking of every last detail. So that you can be better informed about whether a stay is worth your time and money.


Four Seasons Anguilla is by all standards a beautiful hotel sitting on a grand well-manicured property right along Anguilla’s coastline. This means that from any point on the property you are always only a short walk from the beach and some rooms/villas are even closer (at a premium of course).  Better yet, the hotel is a short ride (10mins) from the ferry. While Anguilla has an airport, the most common route is through St Maarten’s airport, from which you’ll take a 25min speedboat to get to Anguilla’s ferry station.  On paper, this sounds like an additional hurdle, but in reality, it’s a lovely opportunity to get a glimpse of another island before settling into Anguilla but even more importantly, the boat ride between islands makes for an exhilarating and fun sightseeing experience.


The property reads brand new and contemporary, I was surprised when a staffer shared that he had been working there for 4 years, I had assumed the hotel must have opened in the last couple of years due to its appearance. This for me is always an important sign of the attention to cleanliness at a hotel. I have been at 6month old hotels that are already showing signs of fatigue and use, and often that doesn’t bode well for the future of the hotel. I do have to say that almost as a general rule, the Four Seasons brand does an excellent job of making sure that its properties maintain a level of cleanliness – I hardly ever have to worry. I should say that individual housekeeping services can vary as we are talking about specific human performance which may not always be equal across the board. Over the course of our stay, all was well. 

We stayed in a pool facing one bedroom suite- fully equipped with a larger than my apartment kitchen, balcony, jacuzzi, living area.  The balcony was accessible from both the living room and the bedroom. If I were to dock half a point anywhere, it would be that I personally would have loved just a tad more color in the living room area to reflect the Caribbean- but that’s more of a personal preference than anything else. 


I am yet to be disappointed by Four Seasons service. Their training program must be super solid- across the board, every single person I came across, from dedicated interactions to passing by, every single staffer was super helpful, super courteous while always maintaining the right amount of “do you need help” with “I’ll let you enjoy your day”.  I say this all the time, but there is a level of too much service that can be intrusive and forced. The b best service is a light touch, not a heavy hand.\


Long story short, there is an expectation of good food at a hotel at this level.  And they definitely hit that mark, but what I look for, what can make Good great, is when the food options reflect the place I’m in. It really disturbs me when hotel kitchen caters to the already established palettes of their guests- with American Pancakes or Italian pasta. This is the Caribbean, I expect to eat Caribbean food and FS Anguilla did not disappoint. They definitely had a varied menu of Italian, American, Asian cuisine, but they also had a sizable menu of Caribbean dishes- not just jerk and curry but also all the staples you’d find at a proper Caribbean restaurant- sailfish, provisions, ackee, bakes and more. 


So, should you stay here? Well, if you like a beautiful property with some of the best beaches and water, if you value service and want to step away from some of the more overly touristed islands, then FS Anguilla will be for you.

PACK: sunscreen, mosquito spray, swimwear, sandals, sunglasses, a good book.



  1. Mary Gilbert

    June 13, 2021 at 3:10 pm Reply

    Great review; love your clothes and style!

  2. holly lombardo

    January 6, 2021 at 1:20 pm Reply

    Because I do alot of business with Four Seasons hotels, my clients always receive :
    Full breakfast for 2 daily
    $100 resort credit
    Free upgrade at ck in if available (( I always try and negotiate at time of booking. Just as I did today and secured a free upgrade for client!)

    Let me know how I can help fans of CYN out!

    1. Jessica

      January 29, 2022 at 6:45 pm Reply

      Hi, how are you? Are you a travel agent?

  3. Khanya

    November 10, 2019 at 7:24 pm Reply

    Hey Cyn,

    The resort and food looks amazing. It’s definitely on my list of places to visit. Where may I find details about EVERYTHING you wore? 😁

Leave a comment