Seasons in the Caribbean revolve around visitor arrivals rather than good or bad weather – which, by the way, is pretty much always good. The True Anguilla team think it’s ALWAYS a good time to visit Anguilla, so here is a brief guide to what to expect in the different seasons.
Festive Season
Two week period surrounding Christmas and New Year’s Eve (called Old Year’s Night in Anguilla)
During Festive Season, hotels and luxury villas are in the highest demand and rates are the most expensive. Our typical guests are large family and friend groups, a high percentage of whom know each other and come every year.
The Four Seasons, Resorts by CuisinArt, Zemi Beach and Cap Juluca hotels will put on fantastic events and special entertainment, but often close their doors to outside guests during this time. So, if you’re staying in more reasonable accommodations, don’t expect to sneak in to spot the celebrities the season attracts! Enjoy watching the world’s best mega yachts light up our normally secluded bays.
If you fancy a visit at Festive, book early and make sure you make your dining and boat charter reservations as soon as you can — direct where possible (see our advertiser directory for more information).
Omalie 360 performs at the Four Seasons 
Maundays Club, Cap Juluca 
Beach Bar & Lounge, CuisinArt Golf Resort & Spa, Anguilla 
Zemi Beach House
High Season
Thanksgiving to Festive and Festive until the end of March.
Expect to pay high (published) rates and to book well in advance, especially oceanfront rooms in properties like Carimar, Frangipani Resort and Shoal Bay Villas, as they often get rebooked year on year for popular dates. Bag a value added villa rate if you book directly with local agents or via the websites of villas like Beaches Edge and Alegria.
During this time, oceanfront restaurants like DaVida, Straw Hat, Trattoria Tramonto and gorgeous garden-set Veya will be busy, so make a reservation.
You should also make reservations at popular sundowner spots like Sand Bar, Roy’s, Johnno’s and Elvis’ Beach Bar in Sandy Ground.
You can also visit and enjoy dining options and nightly entertainment in the major hotels. Expect to meet and make friends with “Anguilla Connoisseurs,” second home owners who are living the dream, and the “snow birds” who flock to Anguilla for 2 to 3 of these peak months every year and usually know more about where to go and what to do than any local!
Low Season
October to Thanksgiving and Easter until end of August
For many this is the best time to visit. The weather is gorgeous, and our waters are at their calmest and most tempting. Expect and enjoy special offers at luxury properties like Kandara & Bird of Paradise; sometimes you can bag a real bargain.
Time your stay to coincide with important local events like Anguilla Day, The Anguilla Lit Fest or Summer Festival, most of which occur during this time. Expect a younger crowd, more regional visitors, honeymooners and the guests of destination weddings and corporate groups having a ball!
This is also the best time to organise a special event or corporate retreat, as the rates are so favourable — for more information talk to Mimi at Blue Sea Anguilla.
Low, Low Season
September & October. Also known as off, hurricane or closed season.
This can be the most rewarding, and is the cheapest time to come, for the traveller looking for an authentic island experience. Most hotels and most beachfront restaurants close for rest and refurbishment (and because of potential for hurricanes) but there are still plenty of charming local accommodations like Paradise Cove or Airbnb spots like Hummingbird to enjoy.
Fine dining is limited, but popular spots like Ocean Echo, Lit Lounge and Tasty’s remain open.
There is plenty of delicious local food on offer and you can always book a villa chef like Chef Tyrone of Hughes Culinary Villa Services to cater to your every culinary need. If you like your weather hot, your beaches completely empty and your Anguillian friends free to spend time with you, it’s a great time to come. Make sure you book somewhere with a/c, though!
A note on Hurricane Season
Atlantic Hurricane Season 2020 begins on 1 June and ends on 30 November. Anguilla has suffered through some major hurricanes, most recently Irma in 2017, but our island is very cognisant of the threat and has an excellent reputation for preparedness and bouncing back. If you are worried about hurricane season, please ensure your travel insurance covers you and check with your chosen property on their hurricane response policy prior to booking.
