The best time to visit Anguilla is December through April, the dry, breezy peak season. Late April into May is the best value, with warm water, thinner crowds and low-season rates from May 1. August through October is the heart of hurricane season, and November is the quiet comeback. Daytime highs stay around 84°F to 88°F all year, and the sea ranges from about 79°F in January to 84°F in September and October, so there is no bad month for weather, only different prices and risks.
Anguilla is a small Caribbean island, so the weather on the island changes less than the prices do. We host guests at Villa Okeanos above Shoal Bay East all year, so this is the honest version, including what each season costs at our villa.
Anguilla weather by season
| Season | Months | Weather | Crowds and prices |
|---|---|---|---|
| Peak season | Mid-December to April | Driest time of year, February is the driest month. Highs around 84°F in December and January, breezy. | Busiest and most expensive. Festive weeks book a year ahead. |
| Shoulder season | May to July | Hotter, highs around 88°F by June, sea warming up. | Quieter, low-season rates. |
| Hurricane season peak | August to October | Hottest and wettest stretch, highs around 88°F, sea about 84°F. September has the highest hurricane risk. | Quietest time on the island. |
| Comeback | November | Still one of the wetter months, warm sea. | Quiet, low-season rates, past the main peak. |
Anguilla gets about 8 hours of sunshine a day in most months and about 9 in March, April and August.
Anguilla month by month
- January: high season resumes January 5 after the holidays. Highs around 84°F, sea about 79°F, dry and breezy. A great time for calm seas, beach days and boat trips.
- February and March: the driest part of the year, with February the driest month. Moonsplash brings live music to Rendezvous Bay in March. Peak demand, so book villas, resorts and car rentals early.
- April: still high season with sunny skies and about 9 hours of sun a day. Festival del Mar fills Island Harbour at Easter, and the Anguilla Culinary Experience starts in late April in 2027.
- May: low-season rates from May 1. Warm water, fewer people, and in our view the best-value month.
- June and July: hot, with highs around 88°F. Hurricane season officially begins June 1, though the risk is low early on. Less crowded beaches like Shoal Bay East and Meads Bay, and the Summer Festival gets going in July.
- August: Summer Festival and boat racing around August Monday. Hot and lively, with hurricane risk rising toward late August.
- September and October: the peak of hurricane season and the rainy season. Sea temperatures reach about 84°F, so snorkeling and marine life are at their warmest, but this is the quietest time on the island.
- November: one of the wetter months, still low-season rates, and quiet as the island gets ready for winter.
- December: high season returns December 1, with highs around 84°F. The festive season from December 20 is the most expensive time of year.
When is hurricane season in Anguilla?
The official Atlantic hurricane season runs from June 1 to November 30. The peak is around September 10, and the Caribbean often sees a second, smaller peak in mid-October. For Anguilla, hurricane conditions are possible from July to November, with September the highest-risk month.
Plenty of people travel in these months without incident, and a tropical storm does not hit Anguilla every year. If you book then, buy travel insurance that covers named storms, keep your plans flexible, and go in with your eyes open.
What each season costs at Villa Okeanos
Our rate card splits the year into four blocks, and the gap between the cheapest and the most expensive night is significant. Rates are for the whole villa, covering up to 8 guests, not per person.
| Season | Dates | Nightly rate | Each extra guest (9 to 11) |
|---|---|---|---|
| High | Dec 1 to 19, 2026 and Jan 5 to Apr 30, 2027 | $1,400 | $100 |
| Festive | Dec 20, 2026 to Jan 4, 2027 | $2,300 | $150 |
| Low | May 1 to Jul 30, 2027 and Aug 13 to Nov 30, 2027 | $1,150 | $50 |
| Carnival | Jul 31 to Aug 12, 2026 | $1,225 | $75 |
The 13% Anguilla Goods and Services Tax, a 10% staff service charge and a $475 departure cleaning fee are added at checkout. Our availability calendar prices every night so you can see the total before you commit to anything.
The best time to visit Anguilla, if you asked us
If someone asked us to choose without looking at price, we would say late April into May. High-season crowds have thinned, the water is warm, and the rate drops to low season on May 1. That first fortnight of May is the best-value stretch on the calendar, and it is not close.
November is the other one. Quiet, still low season, and past the peak of hurricane season, far enough that most people are comfortable with it.
What’s on in Anguilla through the year?
- March: Moonsplash. A music festival held each March at the Dune Preserve beach bar on Rendezvous Bay.
- Easter: Festival del Mar. A festival weekend in Island Harbour with boat racing, just along the coast from the villa.
- Late April to early May: Anguilla Culinary Experience. The 2027 edition is scheduled for April 28 to May 2.
- Late July to early August: Summer Festival. Anguilla’s Carnival, with parades, music and boat racing, the national sport. It centers on August Monday, so the dates shift slightly each year. In 2026 it ran from July 10 to August 9.
Dates for 2027 events are confirmed by the organizers closer to the time, so check before you book around one.
Getting to Anguilla in each season
Whatever the month, you either fly direct to Anguilla’s airport (AXA) or fly into St. Maarten (SXM) and cross by public ferry or private boat, or take the short Anguilla Air Services flight. In peak season, book flights, boat transfers and rental cars early, as they sell out along with accommodation. Our arrival guide covers every route from St. Martin.
In the wetter months, bring insect repellent. The CDC advises avoiding mosquito bites in Anguilla and using repellent with at least 20% DEET.
The seasons with a catch
Festive is beautiful and it is expensive, and it books earliest. If you want Christmas or New Year here, start a year ahead. We are not exaggerating.
Carnival is the one season that moves, because Anguilla ties it to the August Monday holiday. If you are coming specifically for it, check the current dates rather than assuming last year’s, and tell us so we can hold the right nights.
September and October are the quietest and cheapest months, and they are also the heart of hurricane season. Ask us what is open before you book.
What does not change
The five-night minimum applies year round. That is the length below which a villa stay stops being worth the setup for anyone, guests included.
Sea temperature barely moves. Neither does the daily rhythm of the island. Whichever month you land in, the mornings are calm, the afternoons are hot, and the wind picks up in the evening.
Frequently asked questions
Low season. At Villa Okeanos that runs May 1 to July 30 and August 13 to November 30, at $1,150 a night for up to 8 guests.
The wettest stretch runs from late summer into autumn, with September and November among the wettest months. February is the driest.
Yes. Early December is high season with dry, breezy weather. From December 20 to January 4 is the festive season, the most expensive time of year and the first to book up.
About 79°F in January, rising to about 84°F in September and October.
Many people do. The risk is highest in September. Buy travel insurance, watch the forecast, and keep your plans flexible.
Plan your dates
If you tell us roughly when you are thinking of coming and how many of you there are, we will tell you what is open and what it costs. Ask us here, or check the calendar directly. Once your dates are set, the arrival guide and packing list cover the rest.
