Anguilla

Anguilla is a British Overseas Territory, which means the official language is English (British spelling, technically) but the local dialect sounds nothing like London. People speak quickly and with warmth. Locals wave to you while driving.

Wave back. It's not optional — it's just how things work here. The island is conservative outside the beach.

Wearing swimwear into shops is genuinely frowned upon; the local newspaper has literally had to remind visitors to shop with clothes on. No topless or nude sunbathing anywhere. Boat racing is the national sport, not a metaphor.

These races are taken dead seriously. And Here's the thing about the pace: nobody is rushing. Factor that into every plan you make.

Waving while driving is social protocol, not optional. If someone waves at you from their car, wave back. Failing to do so reads as rude, full stop..

Dress codes matter. Beach clothes stay at the beach. The local newspaper has literally printed reminders telling tourists to shop with their clothes on.

Take that seriously.. Topless or nude sunbathing is illegal. No exceptions, no ambiguity..

Locals use last names (or titles like Teacher, Nurse, Doctor) unless you went to school together. Don't assume first-name familiarity too quickly.. Strangers on the road wave.

It's a small island where everyone knows everyone. Play along.. Cash matters more than you'd expect.

Some smaller vendors and beach bars don't take cards. Carry USD — it's widely accepted alongside the Eastern Caribbean Dollar (XCD).. Boat racing is the national sport.

During race days, especially August Monday, the whole island shuts down to watch. Don't plan anything else that day.. Smart casual is expected at fine dining restaurants like Pimms or D Richard's — not a full suit, but not flip-flops either.

Anguilla is one of the safer Caribbean islands. Petty theft happens, particularly on beaches — don't leave valuables unattended. Sandy Ground is fine at night but standard street-smarts apply.

Roads are a genuine hazard: some major roads are in poor condition and drivers have a habit of stopping mid-road with no warning. Medical facilities on the island do not meet US or European hospital standards. Serious injuries often require medical evacuation.

Buy evacuation insurance before you go. Emergency number is 911. No legal restrictions on same-sex relationships.

Accessibility is limited — sidewalks are uneven, ramps are rare, and taxis have no special accommodations.

Anguilla has no direct flights from most US cities. The move is to fly into Princess Juliana International Airport (SXM) on St. Maarten, then take the 25-minute public ferry to Blowing Point.

Ferry operators include GB Ferries, Funtime, and Calypso. One-way runs about $20, plus that $36 departure tax on the way out (cash only, so carry USD). From Miami, American Airlines flies direct into AXA.

From San Juan or Antigua, small regional carriers can get you in too. Once on island, there are zero public buses. Rent a car from Gumbsie's or similar operators ($35–45/day for a compact; you'll need a local license for about $25 extra).

Taxis run fixed rates — airport to Shoal Bay is roughly $20–35. After 10pm, expect a surcharge. Roads to some beaches are unpaved.

Drivers can be unpredictable. Keep your distance and don't expect street signs to save you.