Caribbean sailing: Top tips from two years exploring this cruising paradise

My partner Nick and I spent two years sailing in the Lesser Antilles on our Southerly 38, Ruby Rose, after crossing the Atlantic in November 2015. Entering St Lucia after three weeks at sea we had little idea of what to expect.

Rodney Bay in St Lucia was our first taste of the Caribbean and turned out to be the perfect introduction to cruising this area. There was an abundance of restaurants and bars, as well as the local village of Gros Islet a mile away. Someone from the marina told us to head over on a Friday night for the weekly Jump Up, so when the time came we duly walked down the rickety jetty towards the lights and thumping music.

The streets were thronged with people, locals and tourists alike. There were food stalls lining the street selling all manner of barbecued meat and fish, interspersed with makeshift bars groaning under the weight of jars and bottles bearing hand-written labels. We learned the hard way that purchasing one of these rum punches would ensure a headache the next morning: they were far more potent than the sweet, fruity taste let on.

Soufriere and the unforgettable Pitons of St Lucia make a spectacular welcome for cruisers. Photo: Alamy / Robert Harding World Imagery

We were thrilled with our introduction to the region, thinking that we had quickly identified the ‘real’ Caribbean. However, over the following season we came to learn that this broad term doesn’t encompass the many nuanced differences between cultures in this part of the world.

Despite their similarities, there are no two islands that are truly alike in the Caribbean. Even the French islands that we visited – Martinique, Guadeloupe, St Barth and St Martin – shared only a common language and the same supermarkets; in many other respects they were very different.

The Windward Isles

Nick was desperate to return to the Tobago Cays, which he recalled being utterly idyllic when he’d visited them during his Yachtmaster course several years previously. That had been in the low season. It transpired that the Tobago Cays are a very different place in the middle of January.

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