Anguilla in May

Peak season runs December through April when temperatures hover around 80°F and rainfall stays minimal. This is also when prices skyrocket – expect to pay 50% more for hotels and restaurants during these months. But the weather is absolutely perfect, with trade winds keeping humidity comfortable. The shoulder seasons of November and May offer the best value. Hotel rates drop significantly while weather remains excellent. May brings slightly more rain, but showers are typically brief afternoon affairs that cool things down nicely. Summer months from June through October bring heat, humidity, and hurricane risk. Many restaurants close during this period, and several resorts shut down entirely for renovations. However, those that stay open offer dramatic discounts – sometimes 60% off peak rates. Hurricane season officially runs June through November, with peak risk in August and September. Anguilla's location puts it directly in the hurricane highway, and storms can develop quickly. Travel insurance becomes essential during these months. Christmas and New Year's represent the absolute peak of peak season. Resorts require minimum 7-10 night stays and charge premium rates that can exceed $2,000 per night. Book at least a year in advance for holiday travel. Easter week also sees elevated prices and crowds, though not quite to Christmas levels. Spring breakers from the US tend to choose other Caribbean destinations, keeping Anguilla relatively peaceful even during busy periods.