Jazz and blues

If you’ve made a Barbados landfall, linger into the second week in January for the Barbados Jazz Festival (2010 dates to be announced). Anchor in Carlisle Bay off the Barbados Yacht Club and ask about visitors’ membership; make a base here to visit show venues ranging from plantation houses to sports arenas for all-star contemporary and classic jazz.

Then the Grenadines are a must for music-mad sailors, with the overlapping Mustique Blues Festival, 27 January to 10 February, and the eclectic Bequia Music Festival, 28-31 January. These small islands are only eight miles apart, so energetic crews can bop back and forth and never miss a beat. Moorings are mandatory at Mustique unless they’re all taken; if so, you are permitted to anchor. In Bequia, anchor or negotiate a fee for a mooring.

More in the mood for shaking out a reef than shaking your booty? Make the Port Louis Grenada Sailing Festival, 29 January-2 February, your launch into the Caribbean racing scene. Yacht races under both Caribbean Sailing Association (CSA) and IRC rules, competitive racing for the local sailing workboats, friendly fêtes and Mount Gay ‘red cap’ status make this regatta a winner. Grenada offers many marina and anchorage options.

It’s a sail of some 80 miles from Grenada to Trinidad and worth every inch. Trinidad Carnival is the Holy Grail of Caribbean events. This year’s bacchanal will climax on 15-16 February with fabulously costumed street parades and jumping steel band music. Many visiting sailors arrive early to join a costumed band and get right inside the action. Book a berth at one of the Chaguaramas area’s many marinas or grab a reasonably priced mooring in the bay, then abandon yourself to the revelry.