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 Welcome to the Caribbean at its most seductive. Your gay sailing adventure begins in Le Marin, Martinique, where you’ll set course for the legendary Grenadines. Ahead: turquoise water, volcanic peaks rising from the sea, hidden coves and long evenings at anchor under a burning sky. You’ll swim with turtles in the protected waters of the Tobago Cays, drop anchor off palm-fringed beaches, explore lush islands and settle into the slow, sensual rhythm of Caribbean sailing at its finest.
Out on the Caribbean, everyday worries just drift away. Mornings sparkle in turquoise, inviting swims in clear waters, while gentle breezes carry us past palm-fringed islands and soft white beaches. Days of sun and laughter fade into starry evenings, where the waves and quiet moments with friends make everything feel unforgettable.
This journey offers unforgettable moments and incredible highlights:
• Tobago Cays - snorkel with sea turtles in a reef-protected lagoon
• St. Lucia & the Pitons - volcanic peaks, waterfalls and hot springs
• Mustique - understated glamour and sunset drinks at Basil’s Bar
• Salt Whistle Bay - turquoise water and barefoot island perfection
• Bequia - colourful harbour life and relaxed waterfront evenings
Day 1
You’ll arrive in Le Marin between 2 and 4pm, where your gay sailing adventure in the Caribbean begins. Some of the guys may already have arrived a day earlier, easing into island time. Now the group comes together.
The afternoon is about preparation. Part of the crew heads to the supermarket to stock up on fresh produce, drinks and everything needed for the weeks at sea. After 5pm, you’ll step onto your catamaran for the first time and move into your cabin. Bags are unpacked, the deck becomes familiar, and the reality of the journey ahead begins to sink in.
In the evening, you’ll gather for a relaxed welcome dinner at a local restaurant - a first chance to connect properly before the voyage begins. Technical check-in takes place the following morning, so departure is scheduled for around midday.
Day 2
You’ve been waiting for this moment: lines cast off. Around midday, after the technical check-in, you’ll finally leave the marina in Le Marin and set course south across open water. The sails fill, the coastline of Martinique slowly fades behind you, and your gay sailing adventure truly begins.
Today’s destination is Marigot Bay, St. Lucia - one of the most beautiful natural harbours in the Caribbean. Framed by lush hills and calm, sheltered waters, it’s a place that seems designed for arrival by yacht. By late afternoon, you’ll drop anchor and step onto deck as the light softens. Evenings here are known for their spectacular sunsets, with the sky slowly shifting from gold to the deepest blue.
Day 3
No two days on this gay sailing tour are the same. This morning, you’ll continue south along the coastline towards Vieux Fort, where the Caribbean feels less polished and more authentic. The approach is striking - wide horizons, steady trade winds, and long stretches of untamed shoreline. In town, there’s the chance to explore the local fish market, where the day’s catch is brought in fresh and prices remain refreshingly local. It’s a glimpse into everyday island life - direct, unfiltered, and full of character. If conditions allow, you may also sail across to Maria Island, a protected nature reserve just offshore. It’s wild and uninhabited, home to rare species and fragile ecosystems. When stepping ashore, respect is essential - here, you leave nothing but footprints in the sand and take only the memory of the view.
Day 4
Sailing in the Caribbean starts to feel instinctive. Even if you’re new to it, you’ll begin picking up the rhythm - adjusting lines, reading the wind, feeling how the catamaran responds beneath your feet. The steady trade winds carry you further south on this evolving gay sailing adventure. On the horizon, the volcanic outline of St. Vincent comes into view. Its highest peak rises more than 1,200 metres above the sea, forested slopes rolling down towards the coastline. It’s a powerful sight - dramatic, untamed, unmistakably Caribbean. By afternoon, you’ll enter the sheltered waters of the Blue Lagoon, anchoring in one of the island’s most beautiful natural harbours. Calm, protected and surrounded by lush hills.
Day 5
Today you sail towards the legendary Tobago Cays, a protected marine park scattered across turquoise water like five emerald fragments edged in white sand. As you approach, the colours sharpen - deep blue shifting to luminous aquamarine over shallow reefs. This is one of the defining moments of your gay sailing adventure in the Caribbean. Beneath the surface, sea turtles move calmly through the clear water, joined by rays and bright tropical fish. You’ll anchor inside the lagoon, shielded by the sweeping curve of the Horseshoe Reef, which keeps the Atlantic swell at bay. The water here is calm and impossibly clear, ideal for swimming straight from the catamaran or slipping on a mask and exploring below the surface.
Day 6
After breakfast, you’ll sail on to Union Island, reaching the colourful harbour of Clifton in around two and a half hours. The approach is easy, the water bright and shallow as the catamaran drops anchor safely in the bay. From here, the day is yours to shape. You might head ashore for a walk up to the island’s viewpoint, where the panorama stretches across the surrounding reefs and neighbouring cays. The trade winds carry steadily, and the view alone is worth the climb. Or perhaps you stay closer to the water - a swim straight from the catamaran, salt drying on your skin as you stretch out on deck afterwards. As this is New Year’s Eve, the evening brings a special opportunity to celebrate under the Caribbean sky. These are the decisions that define a gay Caribbean sailing holiday: movement when you want it, time to unwind when you don’t.
Day 7
Sailing through the Caribbean means waking up somewhere new almost every day.
Today’s course leads you to Carriacou, the smaller sister island of Grenada, set quietly within the Lesser Antilles. As you approach, the coastline reveals itself in layers - pale beaches, low green hills, and water so clear the seabed is visible long before you anchor. Carriacou is known for its coral reefs and shallow, luminous bays, making it ideal for swimming and snorkelling straight from the catamaran. There’s nothing exaggerated about it. The colours are exactly as intense as you’ve imagined - deep blues, bright sand, sharp sunlight against open water. Another anchorage, another shift in perspective, another reminder of why this route is one of the most striking in gay Caribbean travel.
Day 8
Another strong sailing day finds its way into the logbook. With steady trade winds behind you, you’ll chart a course back past Clifton Harbour on Union Island, heading once more towards the protected waters of the Tobago Cays. This stretch is about the pleasure of being under sail - open water ahead, the catamaran moving confidently through shifting shades of blue. By now, handling lines and adjusting to the rhythm of the sea feels more natural. You and the guys move with greater ease, the routine onboard settling into something instinctive. As you approach the familiar curve of reef and sand, the islands appear again on the horizon - just as striking as before.
Day 9
You return once more to the luminous waters of the Tobago Cays - and somehow they feel different. More familiar. More yours. The lagoon lies calm between the uninhabited islands, its colours shifting from pale turquoise to deep blue as the light changes. You slip back into the water, snorkelling above coral patches alive with bright tropical fish. Sea turtles move slowly through the shallows. The skipper keeps an eye on the current - gentle, but worth respecting. Out here, the sea always has the final word. Later, you step ashore for a walk along an empty stretch of sand. No roads. No buildings. Just wind, water and the sound of your own footsteps. For a moment, it feels like the island belongs only to you and the guys.
Day 10
Today your gay sailing adventure takes a turn towards quiet glamour. You’ll sail past the private island of Mustique, a six-square-kilometre enclave known for discretion, luxury and distance from the outside world.
As the catamaran approaches, hillside villas appear between palm trees, each carefully positioned for privacy. Among them is the home of Mick Jagger, one of several high-profile residents who’ve chosen Mustique as a retreat. Over the years, names like Bryan Adams, Tommy Hilfiger and Princess Margaret have all been linked to the island - drawn not by spectacle, but by seclusion. There’s no flash, no obvious excess - just controlled elegance set against turquoise sea. Later, you may step ashore to explore the harbour or enjoy a drink at the legendary Basil’s Bar, where evenings unfold at an easy pace.
Day 11
You return to Bequia, often called the "Island of the Clouds", anchoring once more in the wide curve of Admiralty Bay just off Port Elizabeth. The harbour feels familiar now - fishing boats drifting slowly, pastel houses climbing the hillside, the rhythm of island life steady and unforced.
Bequia carries history beneath its relaxed surface. The local Whaling Museum offers insight into the island’s past as one of the few places in the Caribbean with a traditional whaling heritage - a reminder that these waters have long shaped the lives of those who live here. If you’re curious to explore further, you can cross to the island’s eastern side to visit the Old Hegg Turtle Sanctuary, a small conservation initiative dedicated to protecting endangered hawksbill turtles. It’s another layer to this evolving gay Caribbean journey - not just beaches and sailing, but stories, complexity and connection to place.
Day 12
Back on St. Vincent, the day opens up to whatever pace suits you. You might head into Kingstown to wander through the historic Botanical Gardens or climb up to the old fort for sweeping views across the harbour and out to sea. If you’re in the mood for something more active, the Vermont Nature Trail cuts through dense rainforest alive with birdsong and shifting light. It’s a different side of the island - humid, green, and quietly intense. Or perhaps today is about doing less. A stretch of sand, warm water at your feet, a cold drink in hand as the trade winds move lazily through the palms. Even on an adventurous gay sailing tour, there’s room for days like this - where the only plan is to enjoy exactly where you are.
Day 13
By now, you’ve begun to feel what Caribbean sailing is really like. Some stretches carry you smoothly on the wind, with the catamaran leaning gently and the sails drawing you forward, while at other times the breeze softens and the movement slows. There’s something deeply satisfying about this rhythm - moving with the wind, the water, and the moment. Later, there’s another stop along the route, and the evening offers a shift in energy. For those who are in the mood, the island’s bars come alive after dark, Caribbean beats flowing out into the warm night air. Tonight is about music, movement, and staying out a little longer before returning to the calm of the catamaran.
Day 14
Your gay Caribbean sailing adventure is slowly drawing to a close - but there’s no need to rush ahead mentally. Today is about staying present and taking in the details you might have missed before. From the deck, you’ll hear birdsong drifting from shore, the surrounding hills alive with movement and colour. The wind, the sound of water along the hull, the easy rhythm among the guys - it all feels settled. You’ll set sail back towards Martinique, breaking the journey with a midday swim stop in clear, open water. One last dive from the stern. One last stretch out on deck as the sun stays high overhead. By evening, the coastline reappears on the horizon. The light softens, the sea turns darker blue, and you watch the sun sink slowly into the distance - not an ending, just the final chapter of an unforgettable journey.
Day 15
Your gay sailing holiday in the Caribbean comes to an end this morning.
By 9am, it’s time to leave the catamaran - bags packed, cabins cleared, one last look across the marina. Over the past two weeks, you’ve sailed through turquoise lagoons, anchored off volcanic islands, swum with sea turtles and crossed open water powered by wind alone. What began as a gay group adventure has become something more meaningful - shared memories, easy camaraderie, a rhythm you’ll carry home. Now it’s time to head for the airport - sun on your skin, salt still in your hair, and the quiet certainty that this won’t be your last Caribbean voyage.
Please note that depending on the weather conditions, changes may be made to the itinerary. Of course, this is done in discussion with the participants.
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