Every trip through the Grenadines is different. Our route is shaped by the wind, the weather, and the preferences of the crew at the time. No two journeys are ever the same, and that’s exactly how adventure sailing should be. Below are some of the highlights we may explore along the way.

St Lucia – Departure into the Tropics

We cast off from St Lucia, where rainforest-clad peaks rise behind the harbour and the twin Pitons stand like sentinels over the southern coast. Before heading south, we may pause to anchor beneath the towering Pitons or slip into Marigot Bay for a first evening beneath the palms. As fishing skiffs return to harbour and the sun sets behind the hills, we settle into the warm rhythm of the Caribbean. The Grenadines lie ahead, and with the holiday season in full swing, we set out under steady trade winds, ready to explore.

Bequia – The Old Mariner’s Island

Mustique – A Christmas Ashore
Our first major stop brings us to Mustique, perfectly timed for Christmas. The beaches are long, quiet, and uncrowded, with soft sand curving beneath coconut palms. We may swim in warm, crystal-clear water before heading ashore to explore the island’s peaceful trails and quiet village lanes. The hills roll gently inland, where wild tortoises shuffle through the undergrowth and hummingbirds flicker in the shade. As the afternoon breeze cools, we return to the boat for Christmas dinner aboard, anchored beneath the stars. Far from winter, we celebrate in the calm, warm stillness of a tropical Christmas.

Bequia – Island Life in Full Colour

Bequia welcomes us next with its easygoing charm. The waterfront bustles with brightly painted fishing boats, and market stalls brim with tropical fruit, fresh breadfruit, spices, and Christmas garlands strung between stalls. Fishermen mend their nets beneath the shade of sea almond trees, and the scent of grilling snapper drifts on the breeze. We wander narrow streets, meet boatbuilders crafting wooden sloops by hand, and stop for a drink at a tiny beachside café while watching pelicans dive offshore. During the festive season, the town hums gently, full of island life but far from any rush.

Canouan – Quiet Beaches and Festive Calm

Further south, Canouan rises gently from the sea, fringed by long white beaches and shallow coral reefs that shine under the Caribbean sun. The village is small and quiet, its simple roads lined with small houses and coconut palms swaying in the breeze. We may swim ashore for a morning walk beneath the palms, snorkel the reef, or hike up to the island’s high point, where sweeping views stretch across the Grenadines chain. With the festive season still in the air, the days feel unhurried, warm, and peaceful.

Tobago Cays – Nature’s Gift of the Season

The Tobago Cays feel like the Caribbean’s ultimate holiday gift: five tiny islets protected by a vast horseshoe reef. Here, the sea glows turquoise and green, the reefs blaze with colour, and turtles glide through the shallows beneath our keel. We snorkel over coral gardens teeming with reef fish, float lazily in the warm shallows, and watch stingrays stir the sand below. With no settlements or crowds, the holiday atmosphere here is pure simplicity and perfect stillness under wide-open skies as we anchor overnight and watch the stars wheel silently above.

Union Island – Colourful Markets & Holiday Energy

Union Island’s Clifton Harbour offers a burst of energy after the quiet anchorages. The small town bustles with colourful stalls where locals sell fresh produce, coconuts, and handmade crafts beneath awnings strung with lights and festive bunting. Steel drums and reggae mix with Caribbean Christmas songs as beach bars fill with locals and visiting sailors sharing cold drinks and stories. We resupply, explore the town’s narrow streets, and enjoy the island’s vibrant energy as the holiday season rolls on.

Petit St Vincent – The Edge of the Chain

Near the southern tip of the Grenadines lies Petit St Vincent, a tiny island that feels completely removed from the outside world. Its beaches are silent except for the soft hiss of waves breaking gently on the reef. Sea birds drift overhead while fish move through the shallows. We may swim ashore for a walk along the tide line, snorkel the reefs alive with colour, or simply enjoy a slow afternoon on deck, the warm breeze and steady roll of the anchorage framing the final days of the year.

Mayreau – Timeless Caribbean Anchorage

As we begin to turn north, Mayreau offers its timeless charm. The single ridge-top village stands quiet, its simple stone church decorated with Christmas lights looking down across the Tobago Cays. Chickens scratch in the dust beneath mango trees while children play in the narrow lanes. We anchor in Salt Whistle Bay, where coconut palms lean out over the sand and small wooden fishing boats are pulled high up the beach. It’s a perfect place to pause, swim, and soak up the last quiet days before New Year’s Eve.

Marigot Bay – New Year’s Eve Celebration

As New Year’s Eve arrives, we drop anchor in the sheltered waters of Marigot Bay. The hillside glows with lights from palm-fringed bars and small restaurants, where live music plays and locals and sailors gather. Dinghies shuttle between anchored yachts as midnight approaches. We join the celebration onshore or aboard, raising a glass beneath warm skies, with fireworks reflecting off the still water as we welcome the New Year with the gentle sway of the boat beneath our feet.

No Experience? No Problem.

No offshore experience is needed. Many crew join solo, and everyone is fully involved from day one. Whether you are completely new to sailing or looking to build your skills, you’ll be part of every decision, every sail trim, every navigation choice. This is real adventure sailing, built for discovery, learning and the pure satisfaction of crossing open water under sail.

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