Holetown, Barbados

Holetown, Barbados is where you go when you want island life without the chaos. The west coast location means calm waters and fewer hurricanes—this isn’t the rugged Atlantic side. But don’t expect a bustling expat scene; with just 1,600 residents, it’s more of a quiet beach enclave than a full-service city.

The Holetown Festival every February is the one time the place feels crowded. Otherwise, you’re dealing with slow island bureaucracy for everything from visas to utilities. The upside? You can walk everywhere, and crime here is lower than in Bridgetown. Just know your social circle will be tight unless you’re proactive about meeting people. This is for retirees or digital nomads who prioritize safety and scenery over convenience.