We've spent a week or more on at least 10 Caribbean islands with a VRBO, car rental etc with the family. Just did 11 nights on Curacao over this past Xmas/New Years. Our goal is never stay on the same island twice, no matter how amazing. We want to visit them all.
Anguilla is amazing. Most people have never been fortunate enough to spend time on beaches so beautiful. It is what I would describe as a true Caribbean island. Low population, bright colors, friendly locals, no big buildings, tiny beach side restaurants serving food that is off the charts, world class beaches/water and most importantly ....no cruise ports. Its not Americanized or touristy in the slightest.
KGB, if you spend lots of time on St Maarten. Take the ferry across to Anguilla and spend at least 3 or 4 days.
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