Island-hop your way to St Lucia

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After the post-ARC festivities in St Lucia subside, Hares can hustle south to join the new Southern Caribbean Sailing Circuit. Two long strides – St Lucia to Bequia and Bequia to Carriacou – will take you to the Circuit’s first event, the Carriacou Sailing Series (not to be confused with summertime’s annual Carriacou Regatta Festival), scheduled to run from 14-18 January, 2009. This event will properly introduce you to regattas island-style.

Then hop down to the next island south for the Grenada Sailing Festival, 30 January to 3 February. Don’t miss the chance to see the colourful traditional workboat regatta, which is sandwiched between the yacht races.

Then it’s time for some ocean sailing – the 75 miles to Tobago for the Circuit’s final event, the inaugural Tobago Carnival Regatta on 10-14 February.

Insider’s tip: sailing guru Don Street says that the closer to Tobago you get, the stronger the current will be, so navigate carefully during the last 20 miles or so to make sure you are not being swept to the west. He adds: “Get to Tobago early, so you’ll have at least a day to rest before the racing – and partying!”

The fun-loving Trinidadian racing crews in Tobago will no doubt persuade Hares to hurry home with them for the climax of Trinidad Carnival, from 21-24 February, where you’ll meet up with the Party Animals – more of which later.

Once you’ve recovered from Carnival – Aesop’s Hare did take a nap in the middle of the race, remember – head back north. Meet Grenada’s fun-loving sailing community at the Round Grenada Race, which has just moved ahead from its former Easter date and will take place from 13-15 March.

Three weeks should provide a generous and flexible time slot to sail up through all the Grenadines to Bequia. Hares will morph into Easter bunnies at the Bequia Easter Regatta 2009, from 8-13 April, which features daily parties and races for sailing craft, ranging from racing and cruising yachts to local double-enders to models made from coconuts.

Now it’s time to make some bunny-hops northward. Get an early start from Admiralty Bay to sail the 50 or so miles to Soufrière in St Lucia in daylight. If you plan to stop on the leeward coast of St Vincent, Wallilabou is reported to be the best choice, owing to security concerns in some other anchorages.

ARC participants can revisit Marigot and Rodney Bay, or go on to Pigeon Island – from there you’ll leap your next channel to Martinique. See the Tortoises’ trail and choose your anchorages in Martinique and Dominica.

The Around Guadeloupe Race, in interesting point-to-point legs, runs from 20-24 May.  Each destination village hosts post-race shows and dancing. It’s a unique way to get to know an island and its people, especially if you speak some French.

If you’re turning back south for the summer, time your trip to join the Martinique racing set in Fort de France for the popular La Bordée de la Saint Jean race on 20 June.

Hares who plan to transit the Panama Canal or cruise the east coast of North America for the summer can take a different tack by joining the 10th Annual Transcaraibes yacht rally. It starts in Guadeloupe on 4 April, makes stopovers in St Martin, the Dominican Republic, Haiti and Jamaica, and finishes with a gala dinner party in Cienfuegos in Cuba on 28 April. This is a more intimate and laid-back experience than the ARC, with fewer than 40 boats and the longest crossing of about 120 miles.

Cienfuegos can be a jumping-off point for the Western Caribbean or Panama.

Insider’s tip: if you’re heading to the US for the summer, get your US visas (required for all non-citizens arriving by yacht) at the ‘US Interest Section’ (http://havana.usinterestsection.gov), which is tucked inside the Swiss Embassy in Havana.