1. It may not be an obvious choice, but I really like St Kitts and Nevis. Nevis is a small island, steeped in nautical history — Lord Nelson was stationed there back in the day when it was a naval hub. The capital, Charlestown, is rather old and very cool to look at. You can get an inkling of years gone by when the Caribbean was awash with pirates and smugglers.
2. If you want to hang out with billionaires and superyachts then head to Saint Lucia. With the ARC (Atlantic Rally for cruisers), hundreds of yachts flock there each year making the island the most popular Caribbean destination for sail boats making landfall from Europe. It's also a popular cruising location for boats heading north or south to other islands in the Eastern Caribbean. Saint Lucia is within easy reach of the Grenadines and the French Antilles making it an ideal cruising base.
3. One of the biggest regattas around is Antigua Sailing Week, which takes place every April. It's popular with yachts from all around the world and is a great opportunity for sussing out the scene. The best action can be found at Nelson's Dockyard, Falmouth Harbour and English Harbour.
4. Grenada also hosts a sailing festival every January and is brilliant for exploring by boat. The capital St George's is home to one of the largest and most beautiful natural harbours in the Caribbean, so it's well worth a visit.
5. The British Virgin Islands are a fantastic place to sail, like a fairy tale. There are lots of islands so sailing between them takes very little time and the great conditions mean it's pretty safe, even for novices. One of the biggest islands is Virgin Gorda, where the big sailing centre is the Bitter End Yacht Club, a mecca for sailors. The bar is ranked one of the top sailing bars in the world, and it's a perfect place to hang out. They stage a pro-am regatta every November, which means that top sailors from around the world will race using an amateur crew.
A good bet for refreshments is the Soggy Dollar Bar on Jost Van Dyke Island. You've got to jump into the water to get there from the beach. It's a bit of an institution. Another awesome bar is the Willy T on Norman Island — it's an old sailing ship, complete with masts and rigging. You used to be able to climb up the rigging and jump off into the water. Things got pretty raucous after a few cocktails.
British sailor Ben Ainslie is a triple gold and silver Olympic medallist.
Investment management firm J.P. Morgan Asset Management are the title sponsor of Skandia Team GBR member Ben Ainslie's Olympic campaign. For information on their products and services visit www.jpmorganassetmanagement.co.uk
