Anguilla is the sort of island that can feel easy—until a bit of swell finds its way into the wrong bay and reminds you who’s really in charge out here. Most boats start around Road Bay at Sandy Ground, not because it’s perfect, but because it’s practical: decent holding, straightforward dinghy runs, and the paperwork ashore without a long march in the sun.
Once you’ve got your feet under you, the rest is mostly good seamanship and good timing. Watch the wind, give northerly swell the respect it deserves, and keep a spare plan in your back pocket for when the anchorage that looked fine at lunch turns lumpy by dinner.