Speightstown, Barbados

Speightstown feels like old Barbados before the resorts took over. The port still operates, so expect fishing boats unloading catch at dawn and produce trucks rumbling through narrow streets. St. Peter's Platinum Coast means you're sandwiched between million-dollar villas and local rum shops where $5 Bajan fish cakes are the real luxury.

Watch for cruise ship days when the port area gets chaotic. The rolling hills west of town offer cooler breezes but require a car—public transport here is built for beachgoers, not errands. Speightstown works if you want coastal access without the all-inclusive resort vibe, but don't expect digital nomad cafes or expat handholding.