We really enjoyed Anguilla. It is a flat (Coral) Island and is known for its great beaches and fine dining options. Anguilla is relatively “new” in terms of Caribbean tourism, so it is not overly developed – which is nice.
We went in May, which is actually the beginning of low season in Anguilla (and the Caribbean in general). I like going at that time of the year because it is before hurricane season (and heart of summer) – so you don’t have to worry about that. But it is low season, so you avoid the high season rates.