June 2022
Anguilla
Caribbean
FIVE DAYS
ANGUILLA
Island Life
We went to Anguilla as a part of a "President's Club" trip with my company that treats high performing employees to a high-end, all expenses paid vacation once a year. With this being the case, the itinerary was more simple for this trip, but Anguilla is a small island so simple is good. If you were to go, I think 4 nights and 5 days is the perfect amount of time to relax and explore this small, charming island. There weren't any direct flights we could find right to Anguilla, but we were able to fly direct with WestJet from Toronto to St Maarten (SXM), which is right next door. It was a 5 hour, 5 minute flight and cost about $550 USD per person round trip. Once you get to St Maarten, you can take a boat transfer to Anguilla on the Calypso charter departing from the Anguilla-St. Maarten Ferry Terminal (adjacent to SXM). It is a fairly easy and quick transfer, with one nuisance around having to have your passports checked ~3 times at different checkpoints during the transfer since Anguilla is a different country than St. Maarten.
When you arrive at the Anguilla port, you will be met by the hotel staff to take your bags and transfer you to the hotel as your final destination. We stayed at the Four Seasons Anguilla which was extraordinary. Here is a tour of the fantastic hotel and island. If you have never stayed at a Four Seasons hotel, you must at least once in your lifetime. The whole experience is impeccable - from the staff, to the facilities, accommodations, amenities, dining, beaches, etc. it just doesn't get better. Since the hotel was so stunning and we had many colleague friends staying there as well for the trip, we spent most of our time here at the hotel. There were three outdoor pools, a state of the art fitness centre as well as sports pavilion with tennis courts, a basketball court, and a rock climbing wall, and you could even borrow a stand up paddle board or snorkel to explore the beaches. All of the food is equally stunningly expensive and delicious, which makes up for the shock of the bill each time. There are also many local restaurants and restaurants in other hotels just a short few min walk down the beach. One of our favorites was the Straw Hat - they have great breakfast! The beach area itself is pristine with warm, clear water and white, soft sand. We are normally much more active travelers, but the Four Seasons on Anguilla was the perfect setting to just lay back, relax and enjoy the hotel and the sun. Here is what you should and shouldn't do if you go:
Let's start with what you shouldn't to. One activity that is common in Anguilla but that I would not recommend is taking a day trip to Sandy Island just off the coast of Sandy Beach. It is a tiny cay in the middle of the ocean from the Sandy Ground area of Anguilla. It is beautiful and the water was crystal clear, but it really is a very small island with not much to offer, including shade. There are very few trees, a few beach chairs, and one restaurant with a seafood menu. The beers are cold and the food was good enough, but it is wildly expensive. You can expect - after sharing an app and 4 drinks (2 alcoholic, 2 non-alcoholic), and with the boat over for 2 people - the entire day to cost around $400+ CAD. Definitely not worth it (at least in my opinion), to hang out on a plain patch of sand in the middle of the water. I have, however, heard good things about Prickly Pear island, which is nearby as well. If you feel like doing a cay tour, I would recommend a day tour with a short stop for 40 mins or so on Sandy Island, and then continue on for lunch and exploring at Prickly Pear before heading back.
On the other hand, however, one activity that you should do and that I would highly recommend doing while in Anguilla is a Moke Tour with Moke Anguilla. A Moke is a four-seater, open-air, old military style convertible car that is popular in California and the Caribbean. The Mokes are very cool, and this tour is a great way to explore the island. Anguilla is a small island, being 16 miles long and 3 miles wide at the widest point, so you are able to cover the entire island in a half day tour. The tour guides speak amazing English and had]ve deep knowledge of the land. You will be allowed to drive your own Mokes if you wish, which is very fun, and you are given a bluetooth speaker to play music in the car while you drive. Every so often, you will stop at a landmark and get out of the Moke for some photos and a short explanation by the tour guide. Towards the end of the tour, you will also stop at a local beach bar to try some local dishes and enjoy a refreshing beverage before heading back to the hotel. It was one of the best excursions or activities I have done on a Carribean or beach vacation and again I would highly recommend it for anyone visiting Anguilla.
After a few days of exploring, relaxing, driving a Moke, swimming at an isolated cay, eating, drinking, and playing tennis, it is time to head home. Again, I think this is the perfect amount of time for this vacation and this location, but if you wanted to extend your trip, I would suggest doing it on St Maarten before you head home. St Maarten is a bit bigger than Anguilla and seemed to have a lot to offer. One cool thing to see in St Maarten before you take off again - the planes fly super low to land at the airport right over a nearby beach. Patrons can hang out on the beach as the planes fly above and it is a very cool sight. Something fun to do before you leave if you have time!