Hawaii Destination Specialist



Why Go

If you ask Travel + Leisure readers what the best island in the Caribbean is they will likely say Anguilla which they have voted numero uno for the last three years. Feeling the sand between your toes just once while feasting your eyes on the perfectly clear turquoise waters, it will be easy for you to understand how this could be so.


Anguilla is your quintessential sundrenched Caribbean island and without all the cruise ships and high-rises you might find on some of the other islands in the Caribbean. Geographically, Anguilla is the northernmost of the Leeward Islands and 150 miles east of Puerto Rico and just nine miles away from St. Martin, and it is part of the British Caribbean. There is a wide range of accommodation available to suit just about any budget and the beaches are about as perfect as one could wish for. If you are island hopping, there are ferries to/from Saint Martin.

Sadly, Anguilla suffered horribly through Hurricane Irma in September 2017. This was a Category 5 storm when it hit and it leveled many of the homes and schools here. While the topography has bounced back, visiting the island certainly goes a long way to help the locals who are likely still feeling the effects of this devastating storm.


By far, the number one activity in Anguilla has to be relaxation. This is a very laid-back island with over thirty diverse beaches where exploring the different ones could be the extent of your activities, if you so choose.  


If your idea of a great time is kicking back, relaxing, sipping on a cocktail and enjoying a whole lot of not much, then Anguilla is the gift that keeps on giving. One of the good things that has occurred since the hurricane in 2017 is the island-wide remodeling. There are some exquisite places to call home for a few days and to indulge in a bit of luxurious pampering and the excellent cuisine that can be found on the island, all with a fresh new look and feel. For us, this is Anguilla's charm. To just chill-out, have a few spa days and take care of you whether you are on your own or traveling with others.

If it is open, a visit to Sandy Island is a must do. This tiny cay, 2 miles off the coast from Sandy Ground is a great place to relax the day away. You can catch a shuttle called Happiness and be on your way to a little spit of sand with a few palm trees and a bar that will serve you the best rum punch on the island! Another excellent excursion is the Prickly Pear Lobster Lunch Day Sail where you spend the afternoon heading to this cay a bit further away. You can snorkel, swim and enjoy your lobster lunch before heading back to the mainland. 

Finally, if doing a whole lot of not much is getting old, there are other activities like tennis, golf, fishing, horseback riding, cycling, snorkeling and diving. If you have always wanted to learn how to sail, the Anguilla Sailing Association in Sandy Ground can help you to fulfill that dream.


Anguilla is a small island. It is only sixteen miles long and three miles wide with just about 16,000 people living on the island.  Most of these people work in hospitality and they are some of the friendliest in the Caribbean. They are genuinely happy to receive visitors and as mentioned, are still recovering from a disaster that nearly wiped them out. You going here matters!  Relaxing here is the experience and a good deed. The ambiance is so low-key that you will have to fight hard to not decompress. Grab a bicycle, watch some sunrises and some sunsets, get the sand between your toes, and enjoy the beautiful powdery white sand beaches. 

If romance is on your agenda, Anguilla is the perfect island for just that. Whether you are looking for a place for an amazing destination wedding that will delight your guests and deliver you a perfect honeymoon, or just a place to get away with your significant other, Anguilla knows how to turn up the charm and create special experiences.

When To Go

We are of two minds when it comes to visiting islands in the Caribbean. We love off-season travel for a number of reasons. Less fellow travelers, more bang for your buck, and the bonus of having our tourism dollars go a longer way for the local entrepreneurs who could use the business during the low season. However, we do agree that safety is important. So, if you trust your weather reports and all looks good, you might make a last-minute turn and to head to Anguilla. You will benefit from all of that it has to offer and still enjoy great weather because it doesn't vary much here. Another perk to coming in the summer is that this is the best time for diving and snorkeling. The visibility is better as are the deals on airfare and accomodation.

Of course, you can always go during the high season which is obviously after the hurricane season running from June through November. Most people come to Anguilla during the cold northern winters to get away from the chill and enjoy the beautiful weather. Understandable. The very best weather here is in December through March, when you will experience less humidity. 

Other fun times of the year to visit are in August when Anguilla has their annual Carnival and in early May when the Anguilla Annual Yacht Regatta occurs.

Source: NOAA

Temperature - high/low

Precipitation - inches/# of days

Average Climate In

The Valley


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