Sail the Caribbean Windward Islands — island-hopping from Martinique to the Grenadines on a catamaran with a hands-on crew.
This is an Ocean Nomads supported partner trip. Small crew, shared adventure, shaped by the trade winds.

What makes this special
- Sail across multiple island nations: Martinique, St. Lucia, St. Vincent, and the Grenadines
- A multi-adventure trip. Sailing, snorkelling, freediving, kitesurfing, hiking
- Remote anchorages and turquoise bays only reachable by boat
- Small crew on a spacious catamaran, everyone takes part
- May timing: fewer crowds, mango season, and authentic Caribbean vibes
The Journey
What it feels like
Warm water. Trade wind breeze. Waking up at anchor and jumping straight into the Caribbean Sea before breakfast. Days move with the wind. You sail to the next island, snorkel a reef, hike to a viewpoint, or drift through a quiet bay with no one else around. Evenings are simple: cooking together on deck, watching the sun go down, falling asleep to the sound of water against the hull. Each island is different. New colours, new people, new energy. But the rhythm stays the same, unhurried, outdoor, alive.
Route & rhythm
We set sail from Martinique and head south through the Windward Islands toward the Grenadines. The route follows the trade winds: steady, consistent, and perfect for sailing.
The exact route depends on weather and conditions, but the Grenadines are always part of the journey. We sail to remote bays, anchor in protected marine parks, and stop in small island towns along the way.
Passages between islands are short, often just a few hours. Some days we sail longer stretches for mile-building. Other days we stay put, explore, or simply float.
A typical day starts with a swim and coffee on deck. We sail through the morning, arrive somewhere new by afternoon, and spend the rest of the day in the water, on shore, or just being. Most nights we anchor rather than stay in marinas, the boat is your base, the ocean is your backyard.
Possible highlights along the way:
Martinique: French Caribbean, beautiful beaches, bakeries, and provisioning
St. Lucia: The Pitons, hot springs, dramatic hikes
St. Vincent: Raw Caribbean energy, less touristy, more real
Bequia: A sailor favourite, laid-back and social
Union Island: Colourful, windy, gateway to the southern Grenadines
Tobago Cays:Turquoise water, reef-protected anchorages, turtles
Mayreau: Tiny, peaceful, stunning viewpoint above Salt Whistle Bay
Experience
No sailing experience needed. You’ll learn by doing: helming, trimming sails, navigation basics. The catamaran is stable and spacious, making it ideal for first-timers. There’s also the option of kitesurfing at some of the best spots in the Caribbean, with an instructor onboard. Whether you want to learn everything or simply take it in, there’s space for both.
We sail a Lagoon 450 catamaran: stable, spacious, and well-equipped. You’ll share a cabin with one other crew member, each with its own bathroom. Space is comfortable but still a boat. Water and power come from watermakers and solar panels. Meals are shared and included: fresh, simple, provisioned locally. This is not a luxury charter. It’s a hands-on, team-based way of travelling. Everyone helps with sailing, cooking, and daily life onboard.
Intensity ●●●○○
Wild Factor ●●●●○
Comfort ●●●○○
Participation ●●●●○
Moments
Jumping into turquoise water seconds after waking up. Spotting dolphins riding the bow wave. Hiking up to a viewpoint and seeing nothing but ocean and islands. Anchoring in the Tobago Cays with turtles swimming beneath the boat. Eating freshly chopped papaya for breakfast. Watching the green flash at sunset with a coconut in hand. Night swimming in bioluminescent water under a sky full of stars.
What stays with you
- A real feel for Caribbean sailing and island life
- Confidence from being part of the crew, not just watching
- New skills. On the water and in the water
- A sense of what it means to travel slowly and live simply
- Connections with people who see the world the same way


Your Captain
Chris
Chris is a true adventurer and pirate at heart. Always up for any creative ideas, he’s known for his spontaneity and love for surprises. He knows these islands inside out, the best anchorages, the hidden spots, and how to read the trade winds. He’ll teach you what you want to learn.






Included
- 14 days of adventure sailing on a Lagoon 450 catamaran
- 3 daily meals, freshly prepared and locally sourced
- The boat & organisation
- Professional Skipper & Instruction
- Adventurous Shipmates
- Sheets & Towels
Not included
- Transportation to and from the boat
- Personal Travel insurance
- Personal Expensed on Shore
- Optional extras (Kite gear rental or teaching, diving equipment)
Additional Info
What our crew says
“This was one of the most transformative experiences of my life. The crew, the ocean, the people I met — everything was beyond what I expected.”
— Sarah, Canary Islands Sailing 2025
Our Drive: Protecting the Big Blue
Adventure
Real experiences shaped by the elements and curiosity
Community
Like-minded people who become crew, then friends
Impact
Travel consciously & protect what we explore
200+
Trip Alumni
30+
Trips Organized
40+
Nationalities connected
100000+
Ripple Effects
Ocean Nomads Vibes & Values
Ocean Nomads is about more than travel. It’s about living closer to nature, connecting with like-minded people, and stepping into a different rhythm. These trips are where it starts. Learn more about Ocean Nomads.



Trips aligned with a more conscious way of traveling
A community you can tap into along the way
Continue beyond the trip through connection and new opportunities
Ready to adventure?
Ready to go, or still figuring it out? Reach out, we’ll help you find your way.

