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

The Caribbean is a veritable cruising paradise. Terysa Vanderloo shares her tips from two seasons exploring the islands

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Cayo Diablo is an idyllic diving spot off Puerto Rico

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.

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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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I did see my very first turtle there (it lazily swam around the boat, then promptly darted away as I clumsily jumped in the water for a closer look) but the anchorage was otherwise so overcrowded it was fairly unappealing. We left after just one night. Grenada, a little further south, gave us our first insight into ‘liveaboard’ culture.

There is a permanent liveaboard community in Grenada and we quickly fell into a pleasant routine of listening to the radio net in the morning, joining in with themed happy hours each evening, and I was even persuaded to go along to a group yoga class. There was always something to do and it was clear that many people made it to Grenada and then saw little point in moving on. We, however, had the rest of the Caribbean to explore.

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Photo: Alamy / Chris A Crumley

Martinique proved to be a favourite. There are a variety of anchorages along its leeward coast, the most spectacular of which is surely at the foot of Mount Pelée, a volcano that towers above the tiny village on the seafront, and early last century wiped out all but two of its inhabitants when it spectacularly erupted.

The island’s French culture is evident as soon as you step off your dinghy ashore. Baguettes, pastries, wine and cheese are plentiful and there are several hypermarkets out of town for provisioning.

Nick and I spent a long and memorable morning negotiating our way by public transport to the HyperU. Giddy with the range of products at our fingertips, we bought a pressure cooker, a bread machine and filled a trolley with groceries, wine and beer, only to realise that we had no way of transporting all our goodies to the boat. One expensive cab journey and an over owing dinghy ride later, we had finally stocked Ruby Rose.

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Photo: Richard Langdon / Ocean Images

Dominica was another highlight. It is easily the most spectacular island in the Lesser Antilles that we visited: a jumble of forest-covered volcanoes jut into the sky, their peaks often obscured by cloud. One Sunday evening at sunset the local families all converged on the beach where we were anchored.

Swimming in the sea with them, chatting about their lives and watching the kids take turns leaping from the pier, a background of golden-tinted jungle rising behind them, was an experience that will stay with me for a long time. It’s these low-key, everyday experiences that make this cruising life so special.

We continued north to the Leeward Islands, stopping at Les Saintes, a small archipelago of the French Antilles, north of Dominica. It has a strong resemblance to the Atlantic coast of Brittany, not least due to its architecture and excellent restaurants.

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From Les Saintes we made our way to Guadeloupe and Deshaies, where it rained and the wind howled for days on end. We were going stir-crazy being stuck on board and eventually made a break for Antigua. Our punishment was enduring eight hours of being tossed around and feeling seasick before gratefully arriving in Falmouth Harbour.

Here we found many bars and restaurants of unusually high quality (the standard of food in restaurants in the Caribbean is generally not nearly as good as we’re used to in Europe, even on the French islands). We stuck around for the Antigua Classic Yacht Regatta, determined to get our hands on the famous ‘red hats’, given out only at the closing event.

Tickets for the final event were a challenge to get hold of, but we dutifully spent several evenings bar-hopping and ingesting large quantities of rum in order to secure our entry to the party.

After bypassing Nevis and St Kitts due to a rapidly-closing weather window, we spent several very rolly nights in St Barth’s notoriously uncomfortable Gustavia anchorage. I don’t normally ‘do’ rolly anchorages, but for St Barth I was willing to put up with a lot.

The town was extremely picturesque, and as quintessentially French as it’s possible to find in the Caribbean. We had fresh baguettes, cheap wine and fois gras daily, and enjoyed looking in all the upmarket shops.

St Maarten was a necessary stop for us as we had decided to upgrade our tender and do some other boat maintenance. We had planned on a week there, but ended up staying for three; something we were warned about the very first morning on the daily radio net. “This place has a way of sucking you in!” Mike, the net controller, cheerfully informed us.

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The Caribbean is also famed for its sailing regattas. Photo: Paul Wyeth

There was a large and friendly community of liveaboards and cruisers on the island, many of whom were stopping for repairs and maintenance just like us. This meant that every evening at the local hangout Lagoonies there were always familiar faces and we used this opportunity to connect with old friends and make new ones.

The longer we spent in the Caribbean, the more the community became a part of our lives. One weekend we headed to the St John, in the US Virgin Islands, anticipating a quiet few days alone. However, it was not to be. As we picked up a mooring buoy (no anchoring allowed) we were hailed on the radio; friends of ours had seen us on the AIS and were coming on over.

They invited several couples we had never met before but followed on social media, who happened to be in the area. So five couples of a similar age converged and our plans for solitude and recovery were abruptly postponed.

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Photo: Tor Johnson

What followed was a weekend that couldn’t have been better if we’d planned it: by day we went diving for lobster, hiking, and, on one particularly memorable afternoon swam with a dolphin and her calf who seemed just as excited to play with us as we were with them!

It was truly the most magical experience I’ve had while cruising. By night we’d descend on somebody’s boat, eat lobster, drink rum cocktails and be serenaded by the two guitar players and singers of the group.

These few days epitomised what we loved about cruising the Caribbean and it couldn’t have been a better end to our time there. The islands of the Lesser Antilles were varied and each had its own culture, character and distinctive beauty.

Every time we had to move on we felt the pull to stay; only our sense of curiosity and adventure kept us sailing. We were ultimately rewarded with all the friends we’ve met and the beautiful islands we’ve been privileged enough to visit.

The post Caribbean sailing: Top tips from two years exploring this cruising paradise appeared first on Yachting World.

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