Buff Bay, Jamaica

This sleepy backwater has a population of just 4,678 people. The buildings date back to the 1800s, giving it a quaint, historic feel, but the bureaucracy is a persistent headache. The Anglican church on the waterfront is a remnant of the town's former status as a parish capital, before it was split into the present-day parishes.

Buff Bay offers a glimpse of old Jamaica, but don't expect much in the way of modern amenities or entertainment. If you're looking for a slow-paced, low-key retirement option, this could be the place. Otherwise, the lack of development and connectivity make it a tough sell for most expats.