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Best and Worst Time to Visit Anguilla

Susan Laurent
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by Susan Laurent

Anguilla is a small, charming island in the Caribbean. It’s a popular sailing and diving destination for adventurers as well as a safe haven for relaxing family vacations. The beautiful beaches, versatile resorts, lighthearted atmosphere, welcoming local population, and warm weather beckon tourists to this island’s shores, time and again. 

But – when to visit? The climate in this part of the world – the tropics and subtropics – is rather peculiar for those used to four seasons. Rather than hot summers and cold winters, there’s the rainy season, dry season, and hurricane season. Yep, the last one sounds like something you’d want to skirt around. So the best time to visit is the dry season – December to April.

But it’s not all about the weather – how about the best time for water sports? Best time for festivals? Best time to avoid crowds? Read on and learn.


Are you planning a last minute trip to Anguilla? We’ve put together all the resources you’ll need for a fun & safe travel:

🛌  Best & Safest Places to Stay in Anguilla:

👉 Zemi Beach House, LXR Hotels & Resorts – (My recommendation for resort)
👉 Cap Juluca, A Belmond Hotel – (My recommendation for resort)
👉 Four Seasons Resort and Residences – Sea view, Garden, Pool 1 – outdoor
👉 Aurora Anguilla Resort & Golf Club – (My recommendation for resort)

⛱️ Fun Activities & Tours in Anguilla:

👉 The Best Sunset Sail and Cocktail Hour in Anguilla
👉 Night Kayaking with Liquid Glow
👉 St. Maarten 4 Hour Sightseeing Tour

🚗 Best & Safest Anguilla Transportation Services:

👉 Airport Pickup Service – Welcome Pickups
👉 Rent a Car – DiscoverCars

🙏 Stay Safe While Travelling:

👉 Safetywing (for medical insurance)
👉 VisitorsCoverage (for trip insurance)

Put on Some Sunscreen: The Best Time to Visit Anguilla in Terms of Weather

Woman applying Sunscreen

The best time to visit Anguilla is at the peak of the so-called high season, between December and April. During these months, which are part of the dry season in tropical climates, the weather is perfect: the sunshine is relatively mild and the rain is rare. In particular January, February and March, are considered as the driest months in the year, with an average rainfall of around 45 mm (1.8 inches) per month. Simply put, December – April is the best time to visit one of Anguilla’s 33 stunning beaches.

The most popular month in this period is December, followed by March and April. During that time, the hotels on this small Caribbean island are almost fully booked, the tables in restaurants reserved in advance, and the seats of flights sold out.

The average temperature between December and April, which covers most of the high season,  ranges between 28 and 29 degrees Celsius (82 and 84° Fahrenheit). This is perfect weather for snorkeling, swimming, and other water-related activities.

Don’t worry though – even at the peak of the tourist season, Anguilla is not as crowded as its more famous neighbors, like Barbados or the Bahamas.

Save up: The Most Affordable Time to Visit Anguilla


After the strong influx of American and British tourists — Anguilla is an official British overseas territory — during the winter and early-spring holidays, late spring and early summer are significantly calmer and less crowded.

During late spring and summer, Anguilla is less crowded and much more affordable. The hotels sometimes offer as much as 50% discounts. Restaurants are cheaper, as well!

But the downside during this period is the weather. After the peak season ends — at the end of April — the air becomes more humid, rainfall increases in intensity and frequency, and it becomes hotter. The average temperature in the shoulder season (May to July) and the low season (August to November) is 31°C (83°F).

Luckily, even during the wet season Anguilla’s most popular activities — like scuba diving or snorkeling – are available. In fact, they’re cheaper and there’s less of a wait for your turn.

Lastly, although August is not the best time to visit the island, the first week of that month is carnival week — Anguilla’s biggest and most important holiday festival. That part of the year is very colorful, fun, and packed with activities. However, it’s also when the locals take a week off. A lot of establishments and restaurants don’t work during carnival week, so you shouldn’t be surprised if you encounter a few closed doors on your way.

Ugh, People: The Best Time to Visit Anguilla to Avoid Large Crowds

As we mentioned earlier, Anguilla is generally not a very crowded island, in comparison to other more trendy or hip destinations in the Caribbean. It’s popular with families, has a generally rural infrastructure and atmosphere, a low crime rate, and a religious, conservative population. So it’s not a party island to begin with.

But, there are times when this calm island is even calmer. The shoulder season — between May and July — is generally the period in which the last throng of the tourists from the USA and Britain depart the island. The beaches are emptier and calmer, making it the perfect time for visitors who prefer to stay far from the crowds of tourists.

The low season — between August and November — is even emptier. Frequent rainfall and  higher chances of hurricanes drive most tourists away from the Caribbean during this time of year.

Keep in mind that many hotels, resorts, and restaurants also close down during hurricane season, and they stay closed until mid December. Given that peace and quiet in Anguilla often coincides with bad weather and closed establishments, we’re not sure the bargain is worth it.

Prepare to Embark: The Best Time to Visit Anguilla for Sailing

Island Harbour Anguilla

Sailing is the national sport of Anguilla, and a popular attraction that makes this small Caribbean island famous around the world. Its calm, crystal-clear water is the perfect site to enjoy the charms of sailing. The island gets pretty crowded too – once a year, sailors from St. Martin, a nearby Carribean island, come to Anguilla to sail and to share their experience.

Throughout most of the year, the waters around Anguilla are generally calm and tame. There are practically no accidents reported by sailors in Anguilla. But, the most suitable time for sailing  is during the winter and early-spring months. It’s dry and storm-free, warm but not hot.

June to November are hurricane season, which reaches its peak in September and October. So if you’re going to Anguilla specifically to sail, avoid these months.

Pack Your Scuba Masks: The Best Time to Visit Anguilla for Diving

Diving in Anguilla

Anguilla is surrounded by no less than seven marine parks presenting a quintessential Caribbean view. Its famously beautiful and diverse coral reef makes Anguilla a popular destination for all kinds of divers — both seasoned professionals and enthusiastic amateurs.

Diving along the uncanny, mysterious, and sublime beauty of El Buen Consejo — the gigantic galleon that sank during a violent time in human history — is one of the most educational and exciting activities in Anguilla.

While the warm weather welcomes divers all year round, the best time for diving is during winter and early spring, between the months of December and April.

Also, the rains are least frequent in February and March, which makes the corals and the versatile marine life around the island perfectly visible. The storms and the rain not only muddy the water, but also excite the nearby fauna.

Everybody Dance! The Best Time to Visit Anguilla for Festivals

Anguilla is an island of festivals. The city becomes vibrant and colorful, and it’s a true joy to observe the citizens enjoying the local traditions and celebrations. But, during those days, the shops and restaurants are usually closed. Evidently, even the inhabitants of paradise need their vacation.

There are plenty of festivals in Anguila throughout the year, but most of them happen from the beginning of spring to the end of the summer, usually between March and August.

Some of these festivals are:

  • The Moonsplash Festival is celebrating its 33rd year of existence in 2023. The festival brings well-known musicians and it’s had a consistently great music program throughout its lifespan. It starts either in March or in April — at the height of the tourist season — and lasts three days.
  • Festival Del Mar occurs during the most important Christian holiday, Easter, and celebrates all things that either live or come from the sea. The village called Island Harbour has a festival which offers a wide variety of events and activities, such as diving, fishing, and cooking competitions, boat races, and plenty of music and dancing.
  • Anguilla Regatta is all about the national sport of Anguilla — sailing. It usually happens at the end of spring, in May, and its main goal is to promote sailing and to teach young boys and girls how to practice this noble craft. It was established in 2022 and lasts for three days.
  • Anguilla LitFest is a perfect choice for literature lovers, since this interesting and unexpected festival in May celebrates not only writers and poets, but also the written word in general.
  • Anguilla Summer Festival is the most important festival on the island, starting either in July or August, at the peak of the Anguillan summer. It celebrates a major event in Caribbean history — namely, emancipation and abolition of slavery in the British Caribbean.

Simply put, these are the most important festivals on the islands. There are other events and activities as well, but most of the fun happens either in spring or during the summer.

Hurricane Season: The Worst Time to Visit Anguilla

The worst time to visit Anguilla is autumn, especially September and October. After summer ends, the rain intensifies even more, and the hurricane season reaches its peak and goes on until sometime in December, when the new season begins.

There’s a real sense of physical danger during hurricane season. For example, the infamous Hurricane Irma that hit Anguilla in 2017, damaged almost 90% of the island’s infrastructure and government buildings. Also, during September and October, neither diving nor sailing — the two most popular activities in Anguilla — are recommended.

Finally, going to Anguilla in autumn is neither safe nor practical. Most of the hotels, resorts and even restaurants take a break during the low season. Either way, you’ll have a difficult time finding open resorts, especially the best ones.

It’s Vacation Time!

Now, before we wrap things up, let’s do a quick recap of the best and the worst time to visit Anguilla.

The best time to visit this small island in the Caribbean is between winter and late spring, or more precisely, between December and April. During late spring and summer, the temperature starts rising and the island becomes more humid. The absolutely worst time to visit Anguilla is autumn, September and October in particular, when hurricane season is at its peak.

About Susan Laurent
Susan Laurent
I'm passionate about world cultures, travel, and discovering amazing new places. I've spent years traveling the globe, very often alone, so I focus on providing important information about travel safety to travelers that I've gathered from first-hand experience.
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