I had been dreaming of sailing in the Grenadines for many years. Whenever I visited any of the islands–be it Barbados, St Vincent, Bequia, St Lucia, or Jamaica–I looked longingly at the catamarans and sailboats passing by. I often imagined what it might be like to stay on one, to sail between islands and to jump off the side of the boat for a swim in the calm waters of a deserted bay.
But there was always one not-so-small challenge: I didn’t know how to sail, none of my friends could sail, and nobody I knew had a boat. So, I thought it would remain just a dream–until I discovered the option of simply chartering a boat. And that is what we did. Last year, two friends and I chartered a catamaran for seven days, hiring a skipper to sail for us: the fabulous Captain Stanley. We loved it so much that we went back again this year for another seven days of sailing with Captain Stanley. And I know we will go sailing again.
So here are some of my favourite things about sailing in the Grenadines:
Leaving Everything Behind
Staying on a boat is like stepping into another world. You only pack the essentials–a few swim shorts or bikinis, t-shirts, a sarong, a pair of shorts, one nice dress, and good music–and immerse yourself in the beauty and calm of the sea. You’re far away from everything, surrounded only by pristine waters and stunning natural scenery. It’s one of the purest, calming and most beautiful experiences imaginable.
Early Morning Coffees on Deck
Every morning on board, I woke early from the sound of the waves against the boat, quietly made myself a cup of coffee, and sat outside–either on the top deck or the front of the boat and just looked at whichever bay we happened to be moored in. Every morning brought a different island, a different view. Sitting there in absolute silence, watching the sunrise and feeling the gentle rocking of the catamaran, was both magical and calming. Once the rest of the ‘crew’ woke up, we enjoyed a long breakfast and a swim around the boat before heading off to the next island.
The Sweet Charm of Bequia
Sailing from St Vincent to Bequia is a special experience. Bequia is exactly how you imagine the Caribbean to be: sweet little houses dotting the hills around the bay, charming shops along the prettiest main road, makeshift beach bars, and family-run restaurants where you can sit on whale-bone chairs right by the water. For most sailors, Bequia is the first stop when sailing in the Grenadines, and we were no exception. We never miss a chance to visit Bequia. We stocked up on groceries at the small mini-mart in Port Elizabeth, bought precious wine (good wine is a rare find on the islands), and enjoyed a long lunch at one of the many lovely little restaurants along the boardwalk. Our afternoons ended on Princess Margaret Beach, with cold beers, good chats and our toes in the sand.
Everything Tastes Better When Sailing
We did not expect to eat as well as we did while sailing. Everything we home-cooked (or should I say “boat-cooked”?) tasted better after a day of swimming and sailing. There are also so many great places to eat out across the islands, big and small. Some of our highlights included burgers at Basil’s Bar on Mustique, grilled lobster at Big Mama’s Beach Grill in the Tobago Cays, a three-course meal at Soho Beach House on Canouan, dinner at the tiny Tenuta restaurant in Chatham Bay, Union Island. However, without a doubt the best meal we had was the fish Captain Stanley caught for us–barracuda fresh from the sea and grilled within the hour. Marinated in garlic and onions, served with a salad and cold beers, it was absolute bliss.
The Sea, the Wind, the Waves, the Sun
Although none of us were sailors, we adored the long crossings between islands. Imagine sitting on the top deck of a catamaran, under the sails, watching the boat glide through the waves. Sometimes the sea was calm, other times it was “a little rolly,” as Captain Stanley called it. We spent hours taking it all in–just the sea, the sun, and the rhythm of the waves. To make it even more magical, our catamaran had speakers throughout the boat, so we listened to beautiful music while sailing. It could not have been more perfect.
Rum, Coconuts, and a Deserted Island
Believe everything you hear about the uninhabited Tobago Cays. They are as beautiful as everyone says. With crystal-clear water, incredible snorkelling, and empty beaches, they are a highlight of every sailing trip in the Grenadines. This year, Captain Stanley took us to Petit Tabac, a tiny island off the reef, the island Jack Sparrow lost his rum on. We made sure to bring our own Bajan rum and poured it into freshly picked coconuts. Best drink ever.
A Floating Little World
Another delight of sailing was the vendors who came to our boat in dinghies or on surfboards when moored in Bequia or in St. Vincent. Whether it was fresh croissants and pastries for breakfast, water, local fruit, or handmade crafts from shells and coconuts, it feels quite special to buy things while sitting on the back steps of your boat. We still proudly wear the shell bracelets we bought in Wallilabou Bay, St Vincent, during our first trip.
A View to Die For in Mayreau
Like everyone who has the luck to moor at Saltwhistle Bay in Mayreau (population 271), we enjoyed the beauty of the bay with its unique setting, a calm bay separated from the waves only by a small, palm-tree lined strip of beach. But don’t just stay on the beach - walk up the hill. Behind the ruins of the little old Catholic church on top of the hill you will be rewarded with an uninterrupted view of the Tobago Cays and beyond. On your way back treat yourself to a sundowner at Blackboy’s bar on the beach or chill in the Last Bar Before the Jungle.
Celebrating each island Caribbean style
Every island you will see while sailing in the Grenadines is different and unique - charming Bequia, elegant Mustique, remote Mayreau, stunning Tobago Cays, quirky Union Island, cool Canouan. We started to celebrate the delight of experiencing these differences by having a different sundowner on board in every bay we moored in: rum punch in Princess Margaret’s beach in Bequia, beer in Saltwhistle Bay in Mayreau, rum and coconut water in the Tobago Cays, gin tonic in Canouan, margaritas in Chatham Bay in Union Island, and a nice glass of rose in Mustique.
Nights Under the Stars
My last story about our sailing trip is about my favourite moment and one of the most magical experiences in my life. We anchored in the tiny, uninhabited Tobago Cays, and had the best spot close to the reef. As night fell, we were lying in the dark on the trampoline at the front of the catamaran, looking up at the cloudless, black night sky. No light pollution, no noise. Far away from everything. Just the light from the thousands of stars and the soft sound of the waves. The night sky was unbelievably beautiful, I have never seen stars shine so bright. It was like a dome of stars surrounding us, reflected by the dark calm sea. It felt surreal, like a dream. That moment will stay with me forever.
