The "riskiest" time to be in Anguilla is the first 3 weeks of September, plus a couple of weeks before and after.
The island feels very similar to late August and the beginning of October in terms of seclusion and quiet.
Most restaurants and hotels are now closed.
The island sites quietly, hoping for a hurricane-free month.
As for the weather?
Forest Bay, September
The warmest month of the year...
Average High in September: 90°F
Average Low in September: 78°F
Average Temp. in September: 83°F
Average Rain in September: 3"
On top of the weather, most Anguilla bars, restaurants, hotels and villas close up around mid-August and only open again in November.
Yes, September is a real slow, sticky month!
Funny enough, since moving to Anguilla in 2008, September has become my favorite month on the island. Perfectly calm, the seas sparkle something special in September and you almost always have beaches like Meads Bay entirely to yourself.
If you are planning on traveling to Anguilla in September, you will be in for a relaxing treat. Just keep your eyes on the forecast to make sure there aren't any hurricanes on the way.
Anguilla travel tip: September is a hot and humid one. No long-sleeves or long pants!