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MartiniquE Sail
26 Dec. 2026 - 9 Jan. 2027
Spots available
Gay Sailing Trip | Sailing & Relaxation | 15 Days | 6 - 8 Gays
What awaits you
Welcome to the Caribbean at its most seductive. Your 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. This journey offers unforgettable moments and incredible highlights:
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Tobago Cays - snorkel with sea turtles in a reef-protected lagoon
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St. Lucia & the Pitons - volcanic peaks, waterfalls and hot springs
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Mustique - understated glamour and sunset drinks at Basil’s Bar
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Salt Whistle Bay - turquoise water and barefoot island perfection
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Bequia - colourful harbour life and relaxed waterfront evenings
Why Martinique & The Grenadines
The southern Caribbean is a surreal landscape defined by contrast - protected coral lagoons, volcanic peaks rising straight from the sea, and anchorages so clear you can see the seabed from the deck. In the Tobago Cays, you’ll snorkel within the sheltered waters of the Horseshoe Reef, swimming alongside wild sea turtles in their natural habitat.
Beyond the reefs, island life unfolds at its own pace. In Bequia, colourful harbour streets and relaxed waterfront bars invite you to slow down. Fresh lobster is grilled on the beach and rum cocktails are poured generously. On St. Lucia and St. Vincent, rainforest-covered slopes climb steeply from the shoreline, and the iconic Pitons dominate the skyline with unmistakable presence.
Early January is one of the finest times to explore this region. The trade winds are steady, the seas are clear, and the festive crowds have thinned while the islands remain fully alive. Days are deliciously warm; evenings are comfortable on deck, and sailing conditions feel reliable and rewarding. It’s the ideal window for a gay Caribbean sailing adventure - when the air is clear, the wind steady, and the horizon wide open.
Travel package
Accommodation
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14 nights in a shared or single cabin on a comfortable catamaran
Included
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Travel protection and deposit waiver (your deposit is fully protected)
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Bedding and one towel per person
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Final cleaning of the catamaran
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Proof of nautical miles (on request)
Not included
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Meals ashore (everyone pays individually when dining on land)
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Shared on-board expenses (€600–€800) per person), covering groceries and drinks for meals prepared on board, fuel, harbour fees, national park entries, and the skipper’s meals when dining ashore
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Flights and transfers to the marina
Detailed travel itinerary
SHARE a cabin
EUR 2999,-
≈ USD 3464* | ≈ GBP 2594*
Have a cabin ALL TO YOURSELF
EUR 5998,-
≈ USD 6929* | ≈ GBP 5187*
* The USD and GBP prices quoted are approximate conversions of the binding EUR price. The actual USD / GBP amount will vary depending on the conversion rate of the payment service provider on the date of payment.
Picture your trip
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Martin
Your Guys.travel insider
Caribbean Sailing
Tropical Paradise
"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."
Your itinerary
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.
Sailing life
Anyone can sail with us, even if you have no sailing experience at all.
A trained, English-speaking skipper will brief you on how to sail a catamaran and will even let you take part in the navigation of the vessel. As a beginner, you’ll begin to enjoy active sailing after just a few short hours – and you might even decide to take the helm from time to time! But don't worry - our gay sailing trips are uncomplicated adventures that are guaranteed to make your gay sailing holiday one you’ll never forget.
Indeed, everyone is literally “on the same boat” and space is limited.
But no one needs to worry about being too cramped. Everyone has their own bunk, and you’ll also find enough space to relax with others or on your own on deck or in the catamaran's cosy lounge. The shared double cabins are allocated during the introduction round. Couples, friends, and guys who have booked a cabin for themselves are allocated a double or single cabin. Keep in mind that this is not a “clothing-optional” gay sailing trip – so please keep your swimsuits on to avoid making your cabin mate or the rest of the crew feel uncomfortable.
Everyone is involved in running the catamaran.
Daily tasks such as cooking or cleaning are done together and are lots of fun as a group activity. Even though for safety reasons the skipper has the final say on board, everyone is involved in running the yacht – within reason – and actively helps plan the trip.
Yacht
You'll set sail on a catamaran, where space and comfort await you. It accommodates up to 8 men in 4 cabins, with 2-4 shower/WC areas. The catamaran features a fully equipped kitchenette with an oven and refrigerator, a reliable hot water supply, and MP3 connections. Fresh bed linen and towels are provided.
The assignment of cabins among participants takes place during the welcome meeting when boarding the catamaran. Participants sharing a cabin with a confirmed travel partner or those who have booked a single cabin will be allocated a cabin for themselves.
Please note: due to organizational reasons, a last-minute change of yacht type may occasionally be necessary.
Book now
From click to trip
Complete the booking form below
You’ll then receive your booking confirmation by email from our partner, sailwithus, along with an invoice and a travel security certificate.
Secure your booking with a deposit
To confirm your spot, simply pay a 25% deposit of the total trip cost. You can choose to pay by bank transfer or conveniently by Paypal.
Book your flights once minimum group size is reached
As soon as we let you know that the minimum number of participants has been reached, you can go ahead and book your flights.
Settle the remaining balance
The remaining amount is due no later than four weeks before departure. All payment deadlines and details will be outlined in your booking confirmation.
Receive your travel documents
Your travel documents will be sent to you by email directly from sailwithus no later than three weeks before the start of your trip. All that’s left is to pack your bags and look forward to an unforgettable journey.
Tour operator
This Guys.travel gay tour is organised and carried out by sailwithus - the most reviewed provider of sailing holidays in Germany.
When booking the trip, the following Terms and Conditions as well as the Information Sheet for Travelers Participating in Package Travels apply. This sheet provides you with all legally required information prior to booking a package tour in accordance with Section 651a of the German Civil Code (BGB).
Terms and Conditions
of sailwithus GmbH
Information Sheet for Travellers Participating in Package Travels
Download | PDF
