9. St. Kitts Music Festival (Basseterre, St. Kitts; June 25-27)
Originally known as the Shak Shak Festival, the St. Kitts Music Festival has been bringing top acts from across the Caribbean and the world to “Sugar City” since 1996. Acts this year include Bounty Killer, Kerwin Du Bois, Aswad, Benjai, Blaxx, Christopher Martin, Patrice Roberts, the Roy Cape All Stars and T-Vice. R&B star Trey Songz has been tapped to headline, which seems appropriate considering his latest hit (along with Kat DeLuna) is a remake of Sister Nancy’s island classic “Bam Bam.”