Plymouth Jazz Festival (Tobago)

Stevie Wonder (above) performed at the first edition of this festival, now one of the Caribbean’s best in terms of both mood and music, in 2005. The repertoire ranges from late model reggae and soca, to classic R&B and funk. Check Tobago Jazz Fest for programs and tickets, but know that you can usually pick up general admission tickets on festival days at the venue box office. VIP wristbands (from $120 per night) grant access to a special fenced-off area beside the stage with open bar. Traffic is a bear, so hire a taxi to convey you to and from the festival grounds. Stay with the roadies and backup musicians at the beachfront Grand Courlan or splurge on one of the Stonehaven villas where the Plymouth headliners stay.

For more information: Le Grand Courlan or Villas at Stonehaven