Saint George's, Grenada
Monthly cost of living: $2,000
The antidote to the heartless cruise-ship ports and “all-exclusive” resorts that dominate the Caribbean, Grenada is where where a bad attitude is considered an impairment. The so-called “Canada of the Caribbean," -- owing to the neutrality in regional politics -- Grenada only spans 21 by 12 miles if measured in straight lines, but there are months of discovering to be done along its shoreline and lush mountain interior of steep, curvy mountain roads roaming past waterfalls and plantations.
Nightlife? Live calypso bands and upbeat soca music. The hometown dish is a coconut-milk-oil grounded one-pot stew of breadfruit, cabbage, callaloo, dumplings, fish, okra, turmeric, and whatnot; the street version will set you back $2. A buzzing traffic circle near Grand Anse Beach -- the island’s finest -- frames an improvised outdoor marketplace baptized as "Wall Street" because it’s bookended by banks. At night, vehicles blast music, starting parties where locals mingle, dance, buy open-air-grilled meat, and swill beverages peddled from ice chests in pickup beds. Follow the smell of barbecue or the call of steel drums and you’re all set. If you can’t smell or hear something delicious, jump on an incredibly cheap minibus till it happens.