Anguilla is one of the Caribbean’s most exclusive destinations. Here, pristine beaches meet luxury villa living. Plus, the island enjoys steady trade winds and just 35 inches of rain a year (compared to 60+ on many Caribbean islands), giving it some of the region’s most reliable weather. In this post, I’ll go over the best time to visit Anguilla and how it relates to your travel style – from the vibrant energy of high season to the quiet privacy of low season.
When Should You Visit Anguilla? A Month-by-Month Breakdown
| Month | Temp (°F) | Rainfall (in) | Best For |
| January | 77–82 | 2.1 | Peak luxury season |
| February | 77–82 | 1.6 | Romance, events |
| March | 78–84 | 1.8 | Moonsplash Festival |
| April | 80–86 | 2.4 | Perfect weather |
| May | 82–87 | 4.2 | Value luxury |
| June | 83–88 | 3.1 | Pre-hurricane deals |
| July | 84–89 | 3.8 | Summer Festival |
| August | 84–89 | 4.6 | Carnival season |
| September | 83–88 | 5.2 | Hurricane season |
| October | 81–86 | 6.1 | Best villa deals |
| November | 80–84 | 4.8 | Quiet luxury |
| December | 78–82 | 3.2 | Holiday season |
This month-by-month guide highlights the best time to visit Anguilla for weather, crowds, and villa value.
Overall, temperatures typically hover between 75°F and 85°F (24°C – 29°C), with gentle breezes keeping things comfortable even during the warmer months.
The driest months (January-April) offer optimal conditions for outdoor dining at your villa and water activities, while the wettest period (September-November) coincides with hurricane season but provides exceptional privacy and villa rates.
What are the Different Travel Seasons in Anguilla?
High Season (December–April): The Best Time to Visit Anguilla for Guaranteed Luxury
- Guaranteed pristine weather
- Restaurants and beach clubs in full operation
- Active social scene and nightlife
- Ideal time for families to travel together
What to Expect:
- Premium villa rates with 7-night minimum stays
- Advanced booking essential (6+ months recommended)
- Bustling beach clubs and restaurants
- The best time to visit Anguilla for vibrancy and weather
Events Highlights:
Moonsplash Reggae Festival consistently offers an unforgettable line-up, with this year’s event taking place March 5-8, 2026. The Caribbean’s longest-running independent music festival is in its 35th year.
Festival Del Mar also takes place in April over Easter weekend (April 4-5, 2026). It offers boat races, fishing competitions, plenty of sea-related activities for the kids, and seafood galore.
Shoulder Season (May–August): The Best Time to Visit Anguilla for Value & Festivals
For many, the best time to visit Anguilla is between May and August, when you stand the best chance of getting a good package deal and also avoiding the worst of the hurricane season – making this period particularly attractive for luxury villa stays.
Advantages for Villa Guests:
- 20-40% savings on villa rates
- More private beach experiences
- The weather’s still great, with only the occasional shower
- Full villa staff availability and services
Consider This:
- As with the rest of the West Indies, Anguilla enters the hurricane season in June and exits it around November (that said, the risk of a hurricane during shoulder season is very low).
- Some restaurants may have reduced hours
Summer Events
The Anguilla Regatta, held in early May 2026, features thrilling sailboat races and beach parties, celebrating the island’s seafaring tradition.
Anguilla Carnival, also known as the Summer Festival, runs from July 24 to August 9, 2026, peaking on August Monday (August 3), with colorful parades, boat races, calypso competitions, and beach parties commemorating Emancipation Day
Low Season (September–November): The Best Time to Visit Anguilla for Privacy & Savings
Luxury Villa Advantages
- Maximum privacy with nearly deserted beaches
- Exceptional villa rates (up to 50% savings)
- Personalized service with low tourist volume
- Perfect for intimate celebrations or retreats
Important Considerations:
- During this period, the danger of a hurricane or tropical storm increases, especially around August, September, and October
- Some beach clubs and restaurants close temporarily
- Weather can be unpredictable, though hurricanes are relatively rare in Anguilla and most tropical storms are short
What Activities Are Best During Each Season?
When is the Best Time to Swim at the Beach in Anguilla?
December through April offers the calmest seas and most consistent sunshine, ideal for maximizing your villa’s beachfront location.
When is the ideal time to take a boat trip?
May through August provides excellent conditions with fewer crowds, perfect for private yacht charters or even sailing adventures from your villa.
Snorkeling & Diving: When Is Visibility Best?
For underwater lovers, the best time to visit Anguilla is when visibility peaks between December and April. The clearest underwater visibility occurs during the dry season (December-April), making it ideal for exploring nearby reefs accessible from villa-adjacent beaches like Shoal Bay and Little Bay. Many of our Anguilla villas put you steps from the reef.
Check out this post on the 10 best snorkeling spots in the Caribbean for more insider tips.
Cultural Events: When are Anguilla’s Best Festivals?
March: Time your villa stay around Moonsplash for an authentic reggae experience
July-August: Anguilla Summer Festival is the most anticipated event of the year. It’s a ten-day Caribbean Carnival with boat races, costumes, parades, parties and live entertainment.
What’s the Weather Like in Anguilla Year-Round?
Climate Overview
Anguilla enjoys a tropical climate with remarkably stable temperatures year-round, making it ideal for villa stays regardless of season.
Temperature Consistency: Highs rarely exceed 90°F or drop below 75°F
Trade Winds: Constant easterly breezes provide natural cooling
Humidity: Generally comfortable, especially in beachfront locations
Rainfall: Most of the little rainfall Anguilla receives throughout the year comes between July and October, the hurricane season
Seasonal Weather Patterns
Understanding how dry and wet seasons work is key to choosing the best time to visit Anguilla.
Dry Season (December-May): Perfect for villa infinity pools and outdoor dining
Wet Season (June-November): Brief, refreshing showers with sunny intervals
Hurricane Risk: The wettest months are from May to December, and you could encounter hurricane conditions between July and November. That said, Anguilla hasn’t had a direct hurricane hit since 1995 – most storms pass quickly.
How Do Anguilla Prices and Booking Trends Work?
High Season (December–April)
- Villas are in highest demand with limited availability, especially during the holidays.
- Most require longer minimum stays (7–14 nights).
- Booking 6–12 months in advance is essential, especially for holiday weeks.
Shoulder Season (May–August)
- Guests often enjoy more flexibility with stay length and arrival dates.
- Rates are more favorable while villa staff and services remain fully active.
- A great time to upgrade to a larger villa or extend your stay.
Low Season (September–November)
- Villas offer the best value and the quietest beaches.
- Shorter minimum stays are common, with more last-minute openings.
- Perfect for travelers seeking privacy, space, and personalized service.
Smart Booking Tips
- For best villas: Book peak season early.
- For value & flexibility: Choose shoulder season.
- For privacy: Low season offers the most seclusion.
What Travelers Say: Repeat visitors call shoulder season the best time to visit Anguilla for villa privacy without the crowds. Check out this review by Rachel B. for her May trip to the Zenaida Estate in Sandy Hill with Rental Escapes:
“Zenaida Beach & Tennis Resort was an incredible place. It had gorgeous bedrooms, a great little gym, a beautiful pool and hot tub, and immediate access to a private little beach.”
Dreaming of your own beachfront escape? For more villa rental tips, check out Our Answers to 10 FAQ About Villa Rentals.
Where Should You Stay in Anguilla?
Where you stay often depends on when you visit — and choosing the best time to visit Anguilla helps you match the right villa to your season.
Where Should I Stay in Anguilla for Resorts and Dining?
West End & Meads Bay: Premium beachfront villas perfect for high-season luxury
- World-class dining within walking distance
- Sophisticated beach clubs and spas
- Ideal for couples and luxury seekers
Kandara – West End, Anguilla
Where Should I Stay in Anguilla with my Family?
Rendezvous Bay & Shoal Bay Village: Family-friendly villas with iconic beaches
- Expansive beaches perfect for children
- Water sports and activities nearby
- Excellent for multi-generational groups
Alkera – Shoal Bay Village
Where Should I Stay in Anguilla for Privacy?
Little Harbour & Crocus Bay: Secluded villa escapes for ultimate privacy
- Hidden coves and intimate beaches
- Perfect for romantic getaways
- Ideal for low-season stays
Anani – Little Harbour
Where Should I Stay in Anguilla for Exclusivity?
Altamer Resort & Long Bay: Ultra-exclusive villa experiences
- Private resort amenities
- Unparalleled luxury and service
- Best suited for peak season
Villa Nevaeh – Long Bay
Wondering what the best place to stay in Anguilla is for you? Check out this post on Where to Stay in Anguilla for more info on each destination.
When Is the Best Time to Visit Anguilla for Families, Couples, or Groups?
For Families with Children
Optimal: December through April ensures all activities, restaurants, and amenities operate at full capacity, maximizing your villa experience.
For Couples Seeking Romance
Perfect: May through August offers intimate privacy with gentle weather and reduced crowds, ideal for villa honeymoons or anniversaries.
For Budget-Conscious Luxury
Ideal: September through November provides exceptional villa values, though weather flexibility is essential.
For Villa Entertaining
Best: February through April when guests can fully enjoy outdoor villa spaces and island nightlife.
Click here to explore luxury villas in Anguilla.
Summary FAQ: Best Time to Visit Anguilla
When is the best time to visit Anguilla?
December–April for dry weather and full villa services.
What is hurricane season in Anguilla?
June–November, peaking in September and October.
Is Anguilla safe to visit?
Yes, it’s one of the safest Caribbean islands.
What’s the weather like year-round?
Warm (77–87°F) with breezes; driest from January–April.
When are villas most expensive?
December–April, especially around holidays.
When are the cheapest months to visit?
September–November, during low season.
What is the best month for snorkeling?
May–August for the clearest waters.
Are restaurants and hotels open year-round?
Most stay open, though many close in September–October.
When are the biggest festivals?
March (Moonsplash), April (Festival Del Mar), and August (Summer Festival).
Is Anguilla crowded in December?
Yes, holiday season is the busiest—book early.
Ani Anguilla – Little Bay
Ready to Experience Anguilla Villa Luxury?
No matter your travel style, the best time to visit Anguilla comes down to your priorities – perfect weather, cultural energy, or quiet villa escapes. The key is matching your preferences – from weather and activities to privacy and budget – with the island’s distinct seasonal personalities.
Consider your priorities: guaranteed sunshine and full amenities during peak season, balanced weather and value during shoulder months, or maximum privacy and savings during the quieter low season. Each offers its own version of Anguilla luxury.
Explore our luxury Villas in Anguilla and discover how the right season can elevate your Caribbean escape to extraordinary levels.
And if you’re still wondering when the best time to visit Anguilla is for your group, contact Rental Escapes. Your Villa Specialist will be happy to walk through all the best options.
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