Perhaps the best sailing in the Windward Islands centres around the Grenadines and my favourite anchorage in the Tobago Cays marine reserve.

Not one to be jealous of other people’s good fortune, I’m nevertheless a bit wistful that friends from Harbourfront Centre Sailing  are off shortly for a cruise in the Caribbean. In fact, to make things worse, their destination is waters I’ve sailed several times before. 

Blue Lagoon base

Fifteen of the islands belong to St. Vincent to the north and the other six are dependencies of Grenada to the south. Both are members of the British Commonwealth, with the Queen as head of state, so there’s no fuss with other languages, as happens in some of the French and Dutch islands. However, getting there can be a challenge. Flying in to Barbados is easy. It’s the next island hop that can be challenging. Suffice to say, I’ve now heard every excuse imaginable for why my flight is not leaving on time, and I’ve learned my lesson of not trying to schedule flight changes too tightly. Who really needs an excuse for a couple of extra days in Barbados at each end of a sailing holiday? Be warned however that the local joke name for the LIAT Airline is “Leave Island Any Time” … and they do. Sometimes a whole day late. Oh well, they fly on island time and down in the Caribbean, no one is in a hurry.

Getting our charter boat organized

Two of my particular friends are on this present trip. The indomitable Captain Clive, and the charming Amanda, who has been learning to handle my boat for the past two seasons and will be completing her next level of certification on this voyage, under Clive’s tutelage. I shall look forward to hearing all about it when they return. A couple of years ago, we had the pleasure of their company on a lovely sail through the Grenadines, along with our “pirate” friend Taylor. At the Sunsail base in Blue Lagoon, St. Vincent, we pick up our 44 foot sailboat and toss for cabins. As the official charterer I get to pick the best, naturally. The next morning we are off the dock early and the pilot takes us through the secret gap in the reef, not for the faint of heart, as the coral heads can be seen through the limpid blue water. The buoyed “official” channel is actually a bit shallow at low water and we are reminded to radio for pilotage when we return.

Arriving at the dinghy dock in Admiralty Bay with our yacht moored behind

Our first stop is Admiralty Bay in Bequia. Clive and I have been here many times, but it’s a first for the others. We snag a mooring ball right by the dinghy dock and head ashore to explore. I plonk myself down in the nearest bar and quickly assume what I am told is my “big stupid face” when nothing much matters except the arrival of the next rum punch. What the heck, I’m on holiday and we’re not driving or sailing anywhere tonight. We enjoy a delicious curried chicken and rice at the Frangipani which is both a well-established restaurant and a small hotel. It’s a bit of an institution and I’ve eaten here on every visit to the island, but I must say that although the food is up to the usual excellent standard, the service is, as always, lackadaisical. There’s the predictable overnight shower, which means compromising between being too hot and leaving the hatches closed, or getting wet when the downpour happens. I settle for the latter and risk getting the hatches shut quickly when I feel the first splatters on my face. Sometimes that works. Depends on how much rum I’ve consumed, I suppose. At least, by the second night out I’ve worked out how to keep the mosquitoes out of the cabin.

Salt Whistle Bay

Amanda, who I note in the log, is being a wonderful and diligent cook, has made breakfast for all, so we are well fed before we cast off and sail south, past Canouan. During our run to Salt Whistle Bay, we hit a very strong line squall, and we were all very grateful that the experienced Clive is at the helm. When we saw the squall approaching it was too late to reef the main, but we got the jib furled and sailed with a slack main to reduce the pressure. We all got very wet. Amanda gave her pink sailing jacket to Clive, I gave my red sailing jacket to Amanda and Taylor and I ended up braving the elements bare-chested. Taylor, who makes part of his living as a male model on bodice-ripping romance novel covers, looks a lot better bare-chested than I do. Much, much better. But no one was paying any attention to that as we handled the boat in rain so heavy, at times it flattened the sea. We pulled in to a good sheltered harbour on Mayreau and were helped to our anchorage by the usual local, who wanted a tip and a cold beer. This was a bit irritating as I knew exactly where I was going for once, having been here several times before. However, the excellent outdoor restaurant we had been planning to visit had gone out of business since my last visit in 2007, and all that was left were some ruins and an abandoned bar. Much fun and rum was had at a beach BBQ run by some rough looking locals, who turned out to be grand entertainers.

Tobago Cays

It’s not a long run from Mayreau to Tobago Cays. Clive navigated through the channel between Petit Bateau and Baradal and we dropped the hook close by the turtle sanctuary. Amanda again produced a marvelous lunch, and I should note that Taylor was outstanding at bartending duties. Ashore by dinghy to Turtle Island, Clive and Amanda saw turtles and Taylor saw an iguana. I saw nothing, but enjoyed a swim in the lukewarm water. Lots of little boats gathered around every arrival, offering home-made banana bread and ice, which we bought, T-shirts, shell and shark’s teeth jewellery, fresh fish and huge local lobsters. The Caribbean spiny lobster lacks the huge claws of its cold-water cousin but is still delicious. Rather than cook in the confines of a small galley, we arrange for a local man to BBQ for us on a beach on Petit Bateau. I’ve become allergic to shellfish, but red snapper was offered as well. Thank goodness for that, because watching living creatures being tossed onto red hot coals quite put some of our party off their grub. I’m not sure what the difference is between that and plunging a lobster into boiling water , but some folks are squeamish about seeing their food killed and cooked. Imagine that. With fresh banana bread for breakfast and the enticement of a perfect anchorage in paradise, we decided to stay another day. I broke a toe on one of those silly bits that stick up out of every deck and lie in wait for those who insist on going barefoot, so took some serious painkillers and stayed on board while others made the rounds of the little islands and explored.

Tobago Cays anchorage with “Pirates” island on the horizon

On a previous trip to Tobago Cays, I had ventured beyond the reef to Petit Tabac, where scenes from the first Pirates of the Caribbean were filmed.  This is where Johnny Depp playing Captain Jack Sparrow and Keira Knightley his love interest, are abandoned by Geoffrey Rush‘s villainous Captain Barbossa. I mention this to Taylor and he immediately goes into a hilarious caricature of Capt. Jack. We regretfully leave Tobago Cays and tack up the channel between Mayreau and Canouan for our next destination of Mustique. During the preparation and taking up of the mooring ball, I bang my broken toe again and with much on-deck blood and nautical language got the job done. Afterwards Taylor administered soothing straight alcohol. Naturally we had to go ashore to the famous Basil’s Bar. Apparently we had arrived a day late for the big party, so the place was almost empty. The grub was excellent but very expensive, so we were disinclined to linger and headed out instead for a local jump-up. Following the sound of catchy island music along the road, we discovered a much finer celebration, with stalls selling excellent hot snacks and coolers full of beer. This was much more to our taste and our party stayed out quite late.

At the helm well heeled over

Clive went ashore early to pick up delicious French pastries for breakfast and we fed the crumbs to dozens of yellow fish with black stripes that gathered about the boat, accompanied by clouds of tiny silver fish. My toe, now quite blackened, determined I would be feet up for the day, but the others took off for a quick tour of the island to peer at where the celebrities are hiding. I thought it expensive, but they felt it was worthwhile to see where Mick Jagger and Bryan Adams live.

Then it was out to sea again and a close reach up Bequia’s wave pounded east coast before crossing the Bequia channel and back to our home port. Our final dinner was at the French Verandah in the Mariner’s Hotel, where I had a superb curried conch, perhaps the best meal of the trip. The next morning we were up early for flights off the island and just had time to donate all our unfinished bottles of booze to a Swedish couple who had sailed their yacht all the way from Stockholm. Now that would be a real adventure.

Taylor attempts to drink the island dry

PS: I omitted to mention that Taylor is not just a good bod and a great bartender but also an outstanding graphic designer. For our trip down south he designed a great T shirt logo which he is modelling in the picture.