Tobago, Trinidad and Tobago

Life in Tobago is no tropical paradise - the island's economy remains sluggish, with the population of 1.4 million struggling to shake off the legacy of a collapsed sugar industry. While the government has tried to boost the tourism sector, the island's 300 km2 landmass means it sees fewer visitors than its larger counterpart Trinidad. Bureaucracy is a persistent headache, with the Tobago House of Assembly only granted limited self-rule in 1980. And despite its location outside the main hurricane alleys, the island was devastated by Hurricane Flora in 1963, killing 30 people. Those seeking an off-the-beaten-path Caribbean experience may find Tobago's charms worth the tradeoffs, but it's no place for the fainthearted.