Anguilla
Road Bay (Sandy Ground)
Crocus Bay
Little Bay
Prickly Pear Cays
Island Harbour
Day Trip to Sandy Island
Snorkel Prickly Pear Cays
Watch a Traditional Boat Race
Visit The Dune Preserve
Explore the Heritage Collection Museum
Shoal Bay East
Meads Bay
Rendezvous Bay
The Valley
Island Harbour
High season runs from December through April, with steady trade winds, low humidity and daytime temperatures around 27 to 29 degrees Celsius. Hurricane season stretches June to November, and while Anguilla sits within the belt, most direct hits pass to the north or south in any given year. Late April and May offer a good compromise: fewer charter boats, still-reliable weather, and rates that ease off the winter peak.
Anguilla has its own small airport, Clayton J. Lloyd International (AXA), but most visitors fly into Sint Maarten’s Princess Juliana International Airport (SXM) first. From there, a high-speed ferry from Marigot or Blowing Point takes roughly twenty to twenty-five minutes to Road Bay, or a short interisland flight covers the same distance in under ten minutes, reputedly the shortest scheduled international flight in the world. Private yachts typically clear in at Road Bay, also known as Sandy Ground.
Road Bay, also called Sandy Ground, is the main port of entry and a reliable overnight anchorage close to restaurants and bars. Crocus Bay offers calmer water and good snorkeling along its western reef, while Little Bay, tucked beneath cliffs and reachable only by boat or a rope climb down the rock face, is a quieter stop for an afternoon swim. For a full day out, Prickly Pear Cays to the north give the clearest water and best snorkeling of the group.
Two to three days is enough to work through the main beaches and a couple of the boat-only cays, though many guests extend to four or five when Anguilla is the centerpiece of a Leeward Islands itinerary rather than a stop along the way. It pairs naturally with St Martin, a short ferry ride away, and with St Barts a little further south, giving a full week of contrasting islands without long passages between them.
Moonsplash is Anguilla’s homegrown reggae festival, held each March at The Dune Preserve on Rendezvous Bay and founded by local musician Bankie Banx in the late 1980s. It draws touring reggae and roots acts alongside Bankie’s own band, all performing on a stage built from driftwood a few steps from the sand. It is a genuinely local event rather than a resort production, so accommodation books up around it, but it is one of the best reasons to schedule a charter around Anguilla in March specifically.