Many visitors to Anguilla never leave the confines of their hotels for nighttime entertainment, especially in high season when the resorts host barbecues, West Indian parties, and calypso groups and string bands, both local and imported. But who wants to miss out on an essential part of Anguillan culture? For an immersion in the island's lively music scene and a chance to hang with the easy-going, music-loving locals, check the listings in the latest Anguilla Life magazine or ask around -- much of the action is down at the bars in Sandy Ground, and things don't really get cooking until after 11pm. Look for such popular soca/reggae/calypso entertainers as the Musical Brothers, Darvin & his DC Band, and the British Dependency. Dancing the night away -- well, until around 2am, when things wind down -- is absolutely de rigueur.
The island's wonderful beach bars and grills serve great food and drink and feature live music at least 1 day a week.
Keep in mind that Anguilla has no casinos or other gambling spots -- the local Church Council, which has its say in matters such as this, ensures that the island stays that way. If you feel the need for some casino action, St. Maarten and its 14 casinos are just a 20-minute ferry ride (and a short cab ride from there) away.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.