8 Unforgettable Thanksgiving and Autumn Activities in AnguillaDitch the chilly weather this autumn and join us in our Caribbean paradise. While many hotels and resorts in Anguilla close during hurricane season, they open again refreshed and ready to go in October after their annual closures. This is a wonderful time to visit Anguilla before the busy winter high season. The island is less crowded, and you can find some excellent deals on airfare around this time. Anguilla’s beautiful beaches, including our iconic Shoal Bay East, is perfect in the fall for lounging by the sea.