Four Seasons Anguilla – Highly Recommended

Based on travel experiences over the past twenty five years, I’ve developed a high degree of skepticism towards “luxury” in the Caribbean.  My recent stay at the Four Seasons Anguilla demonstrated that it can exist.

Overview: A very strong resort option in the Caribbean
Strengths: Rooms, F&B, Pools, Beach
Drawbacks: Housekeeping
Notable: Basketball and soccer for the kids


Our travel to the property was quite easy with nonstop flights from JFK.  After extraordinarily quick arrival formalities at St. Maarten (SXM) airport (no queue, no forms, no visa, just a quick look at our passports), we were greeted beyond customs by a Four Seasons representative.  They helped us with our bags and brought us to a van waiting just outside the terminal.  The van ride was literally three minutes (most of which queuing in traffic) and brought us to a small (but busy) port facility.  We needed to pre-complete some forms for arrival into Anguilla and then we were escorted onto what was probably a 30 foot pleasure boat (with an enclosed cabin).  We arranged a private boat as the cost was not much more than buying four tickets on a scheduled boat.

Our bags were looked after, though multiple tips were involved with the airport representative, van driver, porter at the port and boat crew (who also helped with the bags).  (Whereas upon our arrival at Cap Cana in the Dominican Republic, there was a lot of unnecessary “employment” prior to customs, here, it seems, the employment graft was during post-arrival transit!  Nevertheless, everyone was nice and things moved quickly.)

The boat ride was about 25 minutes.  Sodas and beers were offered (which we gladly took advantage of) and the crew was friendly.  Reminiscent of our honeymoon trip 17 years ago to the Four Seasons Kuda Huraa in the Maldives, my wife and I found a half hour boat ride upon arrival to be quite civilized and refreshing.

We submitted our arrivals forms when we pulled into the port in Anguilla.  This took a couple of minutes – more than it should have – but just involved us standing in front of the little immigration booth while the officer read through all of our forms and passports.  Another Four Seasons representative met us outside of immigration and brought us to a taxi.  We needed to pay cash for the ride ($39), and a slip was given with the exact fare at the outset so as to avoid controversies.  Within about 15 minutes, we pulled into the property.

We were greeted by the general manager and a colleague who had cold towels and tropical grown up drinks for the adults and other less-festive drinks for the kids.  The check-in formalities were completed while seated on sofas.  The GM, Ilse, had previously been the GM in Seattle (where my wife is from), and they had a lot to talk about.   I was politely thanked for maintaining my Four Seasons Elite status and also for booking through a Four Seasons Preferred Partner agent.  Ilse clearly enjoyed her work and was very visible every day throughout the resort.

Four Seasons Anguilla Lobby
View from the Lobby

Our Room

We were upgraded from a two-bedroom ocean-view residence to a three-bedroom oceanfront townhouse.  This was a generous upgrade and was much appreciated.  Other than one four-bedroom townhouse, we had the top setup away from the villas.

Our Room – “Seaview House 135” (Three-bedroom oceanfront townhouse)

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The unit was set up across two floors with a comfortable living area, dining area and full kitchen.  One bedroom was on the first floor (which included a private outdoor shower and relaxation area).  Two more bedrooms, plus a small office and laundry room, were on the second floor.

The accommodations were quite contemporary.  Some might prefer more local and traditional flourishes, but we found the feel to be quite comfortable.  The room was in great condition with nary a nick or scratch visible.

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There was no minibar, but we ordered a few bottles of wine and a bottle of vodka which more than covered us for our stay.  Surprisingly, there were leftovers!


The master bedroom was upstairs facing the ocean.  Each bedroom had a full private bathroom.  There was an additional powder room on the main floor.


The unit had a large, generally private, outdoor area with a pool (not large, but bigger than a plunge pool), sitting, dining and lounging areas.  There was also a full grill setup (which we did not use).

This is the spa, which was immediately to our left. We did family yoga on this terrace one morning.

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Unlike the pools at Trisara, while they were largely private, they were not completely private as people on the second floor of the adjacent townhouse could catch a glimpse of our pool area (as could we theirs).


The building was built directly onto shoreline rocks.  Though what is shown here is fairly modest, at high tides, the water crashed a good 15 feet up from the rocks and sometimes splashed onto our terrace.

Off in the distance is Malliouhana, an Auberge resort.  A much smaller resort with only 44 rooms (compared to 181 at the Four Seasons), it had almost no family-ready accommodations.  The Four Seasons, despite its size and being very close to capacity, never felt large or crowded.  The majority of the rooms at the Four Seasons are one-bedroom or larger suites/residences/townhouses/villas.  This room mix is ideal for families traveling.  FS-Anguil17-20

Housekeeping – Needs Improvement

Really the only area for improvement evident from our stay at the property was housekeeping.  While the cleaning itself was generally fine (only one exception), the timeliness of housekeeping’s arrivals and their removal of dirty linens and other supplies (or lack thereof) was surprisingly weak.  We typically call and pre-schedule housekeeping based on when we know we will be out of the room.  Most of the days, they did not come at the appointed time – and in several cases, they came hours after when they were expected.  It is very frustrating to come back to the room, expecting some private time, to find the cleaning crew just starting.

In addition, every day, the dirty linens and garbage were left outside of our room.  Presumably, someone else was called to come remove the bags, but these consistently lingered for hours; and in once case, overnight!

The gray towels on the lounging chairs on our terrace were not changed for several days, until we requested it.  It was evident that they were getting a lot of use and housekeeping should seek to change these at some frequency.  Housekeeping also left mops and brooms on several occasions.

At sunset and in the evening, there were a few small bugs out on our terrace.  There were to candle holders outside, but no candles.  I called housekeeping and requested candles and matches.  It took three calls over two days to get candles.  Of course, when the candles came, they did not deliver matches.  It took two more calls to organize those.  The candles definitely helped with the bugs, but the process to get the candles was unacceptable.  (To be clear, the only bugs I encountered were after dark sitting by our private pool in a relatively non-windy spot.  No where else in the property did we face any bug issues.)

I was walking with the GM at one point when we saw these bags (at the entrance to our room).  Her eyes opened quite widely.  I spoke with the her about this and the timeliness issue in a casual conversation.  She was very appreciative of the specific feedback and I got the impression I wasn’t the first to raise the points.  I have a very strong feeling these issues will be resolved in the coming weeks and months.

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Pools and Beach

Beyond the hundred+ private pools located in different rooms, the property has three community pools.  Two were for families, one next to one of the beaches and the other centrally located.  The third was an adults-only pool, located near the lobby.

Service at the pools was very good.  We were consistently greeted upon arrival in the pool area by a waiter who helped set up chairs for us.  Chairs were always available.  While sometimes they were somewhat limited (couldn’t get four together, etc.), even when arriving at peak times, they always made something work.  Importantly, unlike the Four Seasons Palm Beach (where chairs and drinks were handled by separate teams), the people who set up the chairs also looked after food and drink orders.  I really find this combined service approach to be much more guest-oriented.  Tracking down a waiter for drinks or food after arrival was also very easy.  Except for one order which was lost between the bar and the pastry kitchen (and for which the staff was highly apologetic), service was very quick.  There was no “island time” issue whatsoever.

The staff explained they have a two hour chair hold rule.  This helps eliminate the undue chair “dibs-ing” that we faced that Four Seasons Costa Rica or Halekulani.

Having the tree islands in the central family pool helped make for some fun games with the kids.  Multiple families partook in various chasing games.

Central family pool (#1 on the map below)

I didn’t photograph the second family pool (#2 on the map).  It was a bit smaller and had one end that had a beach-style entry, ideal for younger kids.  Service was equally good there.  The water in both was at the cooler end of comfortable; easy to get in to but refreshing to be in.

The adult pool had the best views.  I never made it over here for a swim (as when I had time without the kids, I ended up in our private pool).  From my times walking past it, it seemed to be the most crowded pool area, but still with chairs consistently available.

Adult pool

There were two swimable beaches; one in front of the villas (beach #2 below) and one at the other end of the resort (beach #1 below).  The water was at the strong end of what would be enjoyable.  If you were near the shore, the waves were strong and me, over six feet tall with a solid build, found myself turned upside-down in the wave breakers a few times.  Further out in the water, however, you were beyond where the waves broke and while the water rose and fell, you could comfortably relax.  The water was refreshingly cool but not cold.

The villa beach (shown below in the sunset photos) had some rock breaker walls.  The other beach did not.  Due to the roughness of the water, you didn’t want to be near the breaker walls as getting pushed into them would not be good.

If the water was any rougher, all but the strongest swimmers would be ill-advised to go in.  The waves here, however, provided an active spot for swimmers comfortable in tidal waters.

The sand at the beaches was extremely comfortable – powdery, in fact.  The sand was about as good as it gets.  The service at the beach was also very good with waiters who handled chair set up and drinks.

Sunset at the Villa Beach (Beach #2) – Viewed from the Sunset Lounge (It was like this every night but one)
You can see the strength of the waves



Dining was also a strength.  The food was consistently very good; in some cases, at what I consider to be New York levels.  The property has four open dining venues at present.  A fifth, near the central pool, was not open.

The main (fancy) dining option is Coba.  Breakfast and dinner are served here daily.  Our first night, when we arrived, there was a bit of whispering at the reception desk and we were escorted to the best table in the restaurant (corner, directly on the water).  I suspect this treatment may have been due to the FS card (though they didn’t say anything specifically about it).  They certainly doted on us the entire evening.  Across three dinners and daily breakfasts, we were consistently pleased with the food and service.  We ordered the majority of the fish dishes (something I don’t usually focus on) and were very pleased with each.  Everything (except for the Fundy Bay Salmon) was clearly local and extremely fresh.

Coba’s floor-to-ceiling windows overlooking the ocean were open both at both breakfast and dinner and allowed for a comfortable breeze.  Once or twice at night it got a little windy (blew out our candle, etc), but not too windy.  They kept a small section with the windows closed if you wanted a more indoor feeling.

The Sunset Lounge, shown in the featured photo at the top of this post, offered a diverse set of small plates for dinner; some would call this “tapas,” though many of the dishes had an Asian flair.  Wow.  The food here was very good.  The area itself is more of a bar and lounge (with low tables, etc) than a restaurant, but you could easily make a meal here (as we did on two nights – once with the kids and once without).  Reservations aren’t taken here and our experience was that you needed to arrive 45 minutes before sunset to get a table; or arrive shortly before sunset and you’ll get a table in 20 minutes as others clear out.  Both the food and views (below) were worth the wait.

There was live music several nights – but owing to the open-air setup, you could still comfortably speak without being overwhelmed by the music.  The service was very good and they handled our piecemeal ordering without any issue.


Near the smaller of the family pools was Bamboo.  Another open-air option immediately adjacent to the sea, Bamboo is the more casual option but with a very nice selection.  They also had many of the fish choices from Coba as well as pizzas, Mediterranean options and other choices.  The food was very good here and the service was generally fine.  There were a number of large groups (15+ guests) which sometimes impacted the pace of service for others, but no different than a large group would at a typical restaurant.

Over by the Villas, the Half Shell Beach Bar was a real gem.  Set off from the main property and not heavily signed, this small location had a number of menu options not offered elsewhere on the property.  We arrived at 12:15 one day which was just in time as we got the second to last table.  Those arriving much later had to wait about 45 minutes for a table to free up.  Just like Bamboo, Half Shell was directly on the beach and after lunch, the kids rolled right out into the water.

Consistent with the family-friendly nature of Four Seasons, all of the restaurants had child menus available (including the Sunset Lounge).

The kids ordered room service one night with a babysitter and the food arrived promptly.  I understand the chicken fingers were excellent.

My assistant stayed here a few years back and also had a wonderful stay.  She mentioned that she ventured off property on foot (along Beach #1) and found a few very casual but tasty dining options.

Gym and Other Activities

The hotel has a well-sized gym facility with a variety of small rooms with specific equipment types.  It was one of the better hotel gyms I’ve seen.  We partook in a group yoga class one morning which was offered outdoors on the balcony of the spa, overlooking the ocean (and right next door to our room).  Our son came to the class and the teacher gladly accommodated him.  Beyond yoga, there were other classes – off-property bicycling among others – which if you wanted to be super active were great options.

The hotel also has a full-size basketball court, small soccer field and a rock climbing wall.  There are four +/- (I may have mis-counted) tennis courts, too.  (Our kids really only know club tennis – where whites are required – and they got a kick out of wearing colors for a change!)  There was also an artificial putting green near our room.  Having all of these options gave the kids plenty of things to do out on their own.


For one afternoon, the hotel concierge arranged a sunset catamaran charter.  This was a very nice treat (we did the same thing in Costa Rica) and it was nice to be out on the water for a few hours.

* * * * *

This is a really strong property.  While I’ve not been everywhere I’d like to go in the Caribbean, this was the best property in the region that I’ve been to – without a close second.  The mix of rooms (with lots of suites) is well suited for comfortable family travel.  The food was very good, the beaches were good and there is no island time.  Four hours from New York (plus a 30 minute boat ride)!  How good is that?


Four Seasons Anguilla (formerly the Viceroy)
+1 (264) 497-7000

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