When to go
December to April brings the driest weather and the busiest, priciest weeks, with Christmas and New Year the hardest to book. One seasonal detail shapes where you stay: in winter, Atlantic swells can push waves onto north-west-facing beaches such as Meads Bay, while south-facing Maundays Bay usually stays flat. Late summer and autumn are cheaper but fall in hurricane season, and several restaurants and hotels close for part of September and October.
Getting there
Most visitors fly into Princess Juliana (SXM) on St Maarten and finish by sea to Blowing Point. Shared charter boats from a dock opposite the SXM terminal cost from around US$65 to US$75 per adult and take roughly half an hour; the public ferry from Marigot on the French side is cheaper but needs a taxi across first. Small aircraft also fly into Anguilla's own airport (AXA) from SXM and, in season, San Juan. Boats run less frequently after dark, so a late landing can mean a night on St Maarten.
Where to base yourself
The West End holds most of the luxury stays. Meads Bay is the sociable choice, with nearly a mile of sand and several independent restaurants you can walk to. Maundays Bay is calmer and largely given over to Cap Juluca. Shoal Bay East, on the other side of the island, is a long classic beach with a more casual feel and suits a day trip as much as a base.
How long to stay
Four nights covers beach time and a couple of standout dinners. Seven lets you add a boat trip to Sandy Island or Prickly Pear and a slow loop of the eastern beaches. Taxis charge fixed government fares, so we'd go car-free for short stays and rent for a day or two only on longer trips.