Personally, we love live music, so we're always on the hunt. Every Saturday evening we head to Buccaneer Beach Bar in Simpson Bay to listen to Ronnie and Amin, an incredible acoustic guitar duo playing blues, classic rock. Find the same two guys rocking the house with a full band , Church on Monday at Red Piano Bar. La Bamba Beach Bar has reggae in Saturday, classic rock on Sunday and Latin night on Tuesday. Check the local paper for different venues a different times of the year.
Depending on the time of year, you can find different cultural events such as the I Love My Ram contest (THIS WEEKEND!), Rasta Farm Agricultural Fair, Arrowroot Jollification, Fish Day, Art In The Park and many more. Of course there is always the Heineken Regatta every March and Carnival on both side of the island.
Then, there's the beaches. All 37 of them!