If you’re a digger for partying, enjoying a vibrant local culture and good food, there’s no better place to descend than Jamaica. Its powdery sand beaches and high end resorts are a huge draw, and so is the world renowned music scene (you’ll rarely find a local who can’t sing or do the reggae with adequate swag). Oh! And it isn’t all party and merrymaking here, Jamaica also features some fascinating historic homes, stunning forest waterfalls and an assortment of local delicacies such as jerk chicken and salt fish preparations.
A tiny British territory, Anguilla is accessible only via flights to St. Martin or San Juan, followed by a ferry ride or seaplane journey. While visitors mostly dine at a famous local eatery (lots of celebrity spotting opportunities) or sip on a cocktail at sundown at one of the myriad beach bars here, Anguilla is also known for its stunning spas, private beach resorts and ultra-luxe golf courses. The clear winner here, however, is the food.