8. Cayman Islands

Distance from NYC:  4 hours and 5 minutes

Average hotel room cost: $293 per night 

There are 221 different activities to choose from on the three Cayman Islands. Grand Cayman is the largest and has a cosmopolitan feel to it, thanks to its array of gourmet restaurants, malls, and the beautiful Seven Mile Beach. Cayman Brac has some fantastic diving sights and plenty of serene trails. Little Cayman has uncrowded beaches and one of the world's best wall dives at Bloody Bay Wall. The islands have a high beach-density score of 0.61.