Sailing Expeditions With Impact, Adventure & Community
+/- 400 NM
Best for:
- Multi-adventure experience (Freedive / Kite / Hike)
- Sailing together with fellow Ocean Nomads
- Experience the remote Grenadines island Archipelago when crowds are gone
- Diverse Paradise Destinations at the best time of the year
- Mango rain experience
The image you have in mind from the Caribbean gets beyond confirmed once arrived. The islands are blessed with tropical rainforests, stunning reef drops, waterfalls and adventure potential. It is as scenic above as below the surface. The Caribbean is a truly amazing part of our planet, full of character! Scenic wise with all the happy coloured buildings, the tropical flowers and happy bird sounds. But the real characters are the people.
With dozens of authentic and unique island nations, the Caribbean calls for exploration time. The ONLY way to explore the Caribbean is by sail! With the trade winds from the east and the island chain going from north to south, turquoise waters and thousands of islands, bay and inlets, sailing conditions are just perfect. You have to take the sea route to get the best sense of place and exploration spots.
One of the best secrets: exploring this paradise in May! When the crowds have left, mango season is ON, and authentic Caribbean vibes are present.
This trip we’ll be sailing the Windward Islands in the Eastern Caribbean. The windward islands are the Southern end of the eastern Caribbean island chain. We set sail from Martinique and head down to the Grenadines. They are called windward because you had to beat to windward to get there from other islands. They lie across the easterly trade winds which makes it easy and pleasant to sail north and south. That’s what we will do.
On purpose, we don’t plan out the route in detail (but departure and arrival destination is fixed). Our crew has extensively explored the Caribbean by sail and know about the best and most remote anchorages to choose from. We make the best possible route, with for sure having the Grenadines part of the itinerary. We will go after remote turquoise bays in the Caribbean that can only be reached by sail. We’ll be sailing, snorkeling, riding and exploring the crystal clear waters of the Caribbean seas, where the crowd can’t reach!
Distances between the islands are short. You can usually see the next one already lying ahead of you. That said, we will sail a few hundred miles to make the most out of this expedition. Great for milebuilding too!
You will set sail from Martinique and based on weather head to St. Lucia - St. Vincent - Bequia - Union Island - Tobago Cays - Mayreau and then back.
St. Vincent and the Grenadines
The water cannot get more turquoise than in the Grenadines. Because of its many islands scattered throughout the Caribbean Sea, and the logistical challenges of reaching them, this is where we definitely want to sail! The Tobago Cays are a spectacular protected marine park and legendary for kitesurfing.Cool town: Clifton in Union IslandMust do: sailing and kitesurfingAwesome Beach: Jack Sparrows beach on ‘Petit Tabac’Must eat: Coconuts and red banana.
St. Lucia
This is one of the busier islands in the WindWard Islands. Rodney Bay on St. Lucia is the most advanced location for recycling facilities and waste disposal. Must do: Anchor, dive, hike, and have a chillax session at the hot springs around the PitonsCool town: Soufriere. The vibe is a lot busier and more commercial in the north, while the south is much more authentic and absolutely gorgeous.
Martinique
As it is French territory, you'll spot people walking around with the stereotypical baguette under their arm. It’s a well-developed island with plenty of shops and facilities, making it a popular place for provisioning and sourcing things. Martinique is one of the islands we have not personally explored inside out. We'd love to do that together with you!
Martinique → St. Lucia: ~25 NM
St. Lucia → St. Vincent: ~40 NM (longest, most offshore-feeling leg)
St. Vincent → Bequia: ~10 NM (short and sweet)
Island hopping through the Grenadines: very short hops, often just a few hours
Martinique: French Caribbean with beautiful beaches, hiking and our favorite... french bakeries
St. Lucia: Dramatic scenery for hikes and exploring, especially the Pitons
St. Vincent: Less touristy and has more raw Caribbean energy.
Bequia: A sailor favorite, friendly, laid-back, and social.
Union Island: Windy, colorful, kite-surfing hub and gateway to the southern Grenadines.
Tobago Cays: Absolute highlight—turquoise water, reef-protected anchorages, turtles everywhere.
Mayreau: Tiny, peaceful, with one of the best viewpoints in the Caribbean from the hill above Salt Whistle Bay.
This route is:
Adventurous but not intimidating
Wild nature mixed with strong island culture
Perfect for learning passage-making, catamaran sailing and enjoying island life
Discover what it feels like to wake up on anchor, jump in the Caribbean sea first thing in the morning. breathe the healthy ocean air, have the wind in your hair, live simple and resourceful, and explore like the explorers back in the days. Day in, day out….
If two-thirds of our world is ocean, why do we spend most our lives on land? There’s a whole watery world to be explored out there. Exploring by boat gives the ultimate feeling of freedom. You just go where the wind blows. It’s a sustainable and adventurous way to travel long distances.
A sailboat can bring you to places where no one else goes, while being entirely surrounded by nature.
This is not just a sailing trip, but one for adventure and island exploration!
Imagine jumping into warm turquoise waters just seconds after you wake up. Eating a freshly chopped papaya for breakfast, having consistent 15-20 knot breeze when sailing to the next island, and if we’re lucky spotting a whale or dolphins, hiking up a hill for the view, climbing a palm tree for a coconut, and enjoying a sunset chillax with that coconut and green flash on the horizon. You can work on your swimming skills immersed in the evening bioluminescence, with the starry sky above you making wishes.
That’s just one example of a day on board in the Caribbean. Each day you’ll experience something new, whether it’s landing a new trick, discovering a new island or trying some of the best local Caribbean cuisine.
Ocean Nomads trips and collaborations are beyond ‘the usual’ sailing holiday. It’s and adventure experience aimed at making the dream lifestyle reality, not just for the time with us but beyond all that. Incorporating the Ocean Nomads values, of community, exploration, and positive impact into the elements of the trip. Our trips are always hands-on, everyone helps with the running of the ship. Read more about that on the big Expedition ON overview page.
We’ll touch remote islands that can’t be reached any other way than by boat. Wherever we go we leave the places cleaner than we find it. Beach clean ups are part of the routine, not ‘just’ incorporated as an event.
Most nights are spent anchored, not in marinas. You can swim and snorkel straight from the boat, dinghy to beach bars, and fall asleep to trade-wind breezes.
This is a muti-adventure trip. But ofcourse, you’re always welcome to chill and read a book or just do nothing, but BEing.
As sailors, we’re after wind. The trade winds cover a broad belt from West Africa to the Caribbean. They are called ‘trade winds’ because back in the days, these winds made it possible to bring goods to other places for trading.
During May, the typical winds are between 10–20 knot which is still great for sailing, but less intense than Jan–March. There will be way fewer crowds than winter which will allow you to enjoy sunny, and breezy days and with wild turqoise bays sometimes completely for ourselves. Lush, green islands from earlier rains. The anchorages and towns will also be more relaxed. And it's raining mangoes!
Air: ~80–86°F (27–30°C)
Water: ~80–82°F (27–28°C)
Warm days and breezy, comfortable nights... what else could you ask for!
Wind & Sailing Conditions
The winds in these island are steady and travel south typically, which makes for fast, fun passages. Average wind speeds of 15–25 knots most days, with occasional stronger gusts in the channels between islands.
Where usually this vessel carries our kiteboarding cruises, this voyage is perfect for those seeking to dip their toes in a little bit of everything. We can facilitate kitesurf introductions and we will also sail to legendary kitesurf spots. However this is a multi adventure. Perfect for the couples or travelbuddies who want to have a great mix of activity.
From beginner to advanced kitesurfers can be faciliated We have our on board kitesurf instructor. We have a strong outboard and big tender to bring and pick you up fast, where necessary. We can launch easily from a beach close, or from the boat. Your trip leaders are experienced kite surfers.
It’s the people who make the adventure. We carefully curate a diverse, multi-skilled crew who share a similar mindset, to create a powerful team mix. It makes the difference.
We live beyond the status quo or desire to do so. We care for the planet. Minimize, simplify and cut down on our environmental footprint where we can. We lift each other up and support each other when in need.
Professional Crew & Instruction
The vessel is managed by a professional crew and captain. You’ll be in safe, qualified and experienced hands. This doesn’t mean you only sit back and relax (thought on this trip you can if you want). Generally ON voyages are hands-on voyage involving everyone in sailing and operation of our little floating village.
You?
Adventurer & explorer
Alternative lifestyle seeker
Striving to do good
Excited to share skills and stories
Eager to learn, share and care
Hands-on mindset
Ambitious
Saying Hell Yeah that’s me when reading more about the Ocean Nomads community
What to expect?
Adventure & Exploration: new destination, ocean wildlife and Caribbean Island Exploration with a cool laid back crew
Teamwork: communal living, crew roles, possible watch shifts
Meals & Provisions included: 3 daily meals with fresh, shared meals, soft drinks
Self-Sufficiency: Watermaker, Solar panels
Wildlife Encounters: dolphins, flying fish, occasional whales
Nights on anchor: Enjoy anchoring in beautiful locations with starry skies and amoonlit ocean
No prior sailing experience is needed, just an open mind, a team spirit, and a sense of adventure!
The Lagoon 450 catamaran is the most successful addition to the Lagoon family. The Lagoon design combines spacious living comfort with great sailing abilities. Huge living area inside and out, electric toilets for ease of use and perfect for trips up to 8 Ocean Nomads.
The catamaran is thoroughly inspected, maintained by certified marine technicians, and equipped with the latest safety features, including advanced navigation systems, modern communication tools, life-saving equipment, and redundancy systems to ensure reliability in every situation.
The catamarans feature spacious living areas, private cabins with en-suite bathrooms, fully equipped kitchens, and generous outdoor lounges perfect for sunset dinners or stargazing on deck. The double-hull design offers outstanding stability and smooth sailing, even in changing sea conditions – making it ideal for families, groups of friends, or first-time sailors.
Their goal is simple: to make you feel safe, supported, and completely at home on board.
What's great about sailing a catamaran in the Caribbean is that we can anchor in shallow depths, making it easier to explore the islands.
Protecting the ocean is at the core of the Ocean Nomads community. The Ocean is the heart of the planet. Water covers more than two-thirds of the Earth’s surface. It provides us with food, jobs, life, entertainment, and sailing! Without it, we cannot survive. We believe that by getting the ocean into people’s heart, one starts caring more accordingly. The best way? To help you get you out there and have you experience the magic for yourself.
Most of us spend more time indoors than outdoors. It’s easy to forget the natural world we’re coming from and living in. On the ocean, you face the wind and water elements and find that connection to nature. Imagine a scene with no traffic, no news, no pollution, no civilisation. Just wind and water – plenty of that! A scene where you can gaze for hours to the millions of stars above you; enjoy the dozens of dolphins sliding through the water at the bow of the boat; admire the pink-orange-red sunrises and sunsets, without any airplane trails changing the fluffy and cauliflower-like cloud patterns.
You’ll become very aware of the natural world around you. This inspires. And it’s eye-opening. You come to realise how disconnected from nature we are in our daily lives. In the middle of nature, far away from civilisation, you will see human impact. Usually we’re far away. It’s hard to make it tangible. It doesn’t really affect us. Or so we think. But by being out there, you literally broaden your horizon. Experience will make you think, gain fresh perspectives, and may inspire you to act to turn the tide of the ocean challenges.
We like for you to see for yourself how beautiful the ocean are! And hopefully ignite the supersupower within you to take steps into a conscious nomadic life in or near the sea.
Feel free to contact us with any questions sending an email to ahoy@oceannomads.co
How Ocean Nomads Supports:
Ocean Nomads helps you to be well prepared for this voyage. This trip is operated by Jana & Chris from Ocean Ad Ventures.
Ocean Nomads supports bringing cool people to the voyage but won't be present on board this time for the on board programme.
- Max 6 Passengers ( 8 total crew)
- You don't need prior sailing experience. You'll be taught the ropes.
- Everyone on board will be in a watch team.
- If you’re looking to bring extra sports gear (like surfboards / kitesurf gear / diving gear / bicycles) the vessel can facilitate to a certain extent. There is limited space so please ask permission in advance.
- You're booking is auto-accepted but will still be reviewed by Ocean Ad Ventures to align expectations.
When you book before with Ocean Nomads before April 10 2026, you'll also get:
- 1 Year Access to the Ocean Nomads Crew Course helps you to be prepared, pack, be safe, and be ready for offshore sailing (Valued 297 euro) + 1 year Ocean Nomads Community for more personal support, adventure friends and meeting those who sailed the Atlantic before (Valued 75 euro / year)
To reserve your spot:
Make your deposit to reserve your spot via Ocean Nomads and claim the bonus goodies:)
Then, soon after you'll receive an invoice directly from Ocean Ad Ventures.
Atlantic Crossing voyages usually sell out quite some time in advance. If you're considering joining, don't wait too long;)
"It’s amazing how many awesome friends you can make, and how much just one week on an ON trip can change your life" - Marcin from Poland
“The most unforgettable week. The trip preparation and the crew members turned what would otherwise be an adventure into something a special. I took part in two ocean nomads trips so far. To say it was life changing sounds dramatic but it really was. Being able to share time and experiences with people with different backgrounds but of a similar mindset was incredible. I like to think that I can have and help contribute to a similar experience for myself and others as a member of the Flotilla crew.” – Ben Clipstone from Australia
“In my opinion Ocean Nomads sailing adventure are: 1. A reward for the senses by discovering incredibly beautiful places and breathtaking sceneries. 2. An unbeatable way to get introduced into the world of a sailing lifestyle 3. An open window to learn watching our world and the people from another more conscious perspective. I see Suzanne as an inspirational person who, with her example, inspire others with ideas and proposals to define or redefine life projects and use inner energy for more noble purposes. Our oceans need strong committed people like her to advocate for our natural resources and leave them intact for the generations to come.” – Jose Perez from Spain
"My lifelong dream has been to spend time outside of the US, explore different places, meet , new people and just live somewhere different than what I grew up with. If you told me this time last year that I would have spent the better part the last 365 days sailing around The Canary Islands, surfing in Ireland, sleeping in a van ALONE in England and writing this newsletter on an island in the Adriatic Sea, I would have rolled my eyes at you. But after joining Ocean Nomads on SV Twister a little over a year ago my life has done a complete 180° ( in the best way possible) and I have the network and so many of you to thank for that! – Brianna SV Twister '21
"The experience on twister with other Ocean Nomads was just really beautiful and I felt connected for the first time in decades, I felt part of a community and had companionship. I was so happy that it’s so all inclusive of gender race religion nationality and most importantly age. It has connected me with like-minded people of all ages and being very transformational personally because my life has been incredibly isolated as a single parent Who works from home. I can honestly say October and November I felt happy and free for the first time in maybe 22 years. It gave me everything I was looking for. It has opened up so many possibilities to meet new people with similar vibes, including connection, companionship, purpose and being one with nature." - Cay, SV Twister '21
Check our more Stories, Testimonials & Transformations
on our website or on our Facebook page.
Sail to different Caribbean Countries
3 meals daily, snacks and Soft drinks for the duration of the journey. Everybody will help in the kitchen to prepare the food.
A shared double cabin with a private bathroom.
A hands-on sailing adventure guided by experienced skippers.
From stargazing under clear skies to spotting dolphins and feeling the thrill of open-ocean sailing, every day brings memories you’ll cherish.
Marina Fees & Fue
Pillow & Blanker
A unique and curated mix of adventurous & impact-driven salty souls
Transport to and from boat destination
Personal Travel insurance
To and from the boat
Sometimes if the crew and you decide to enjoy a night out at a re
Check check double check
Enquire for possibilities
We'll be sailing in and out of different anchorages, islands, countries. We have lot of ideas where to go. We let the route also depend on your individual wishes and preferences. Together we make it legendary!
ADVENTURE | Our coastal trips days include a mix of sailing, jumping in the sea, snorkelling, exploring islands, cultural interaction, freediving, kitesurfing, finding treasures, hiking, SUPping. We try to avoid marinas, so we can be closer to nature.
SPONTANEITY | We run our trips rather spontaneously on purpose. We’re dependent on the weather. We go with the flow, and we may change course to explore what we find on the way. We embrace the art of getting lost. We don’t plan out our routes into detail (except for the departure and arrival destination). On purpose.
SAILING | You don’t need sailing experience. Captains we work with are professionally qualified and teach you the basics (and much more if you want), helping you become a competent crew member – or building upon any existing skills you do have. We can sign off miles and give you a reference if you need one. We take care of onboard duties as a group.
VESSELS | This Expedition we work with a spacious, luxurious catamaran to get you closest to the wild islands.
Almost every day there will be the opportunity to kitesurf. We have our on board instructor Jonatan happy introducing you to the sport. Optionally we can also provide more lessons. As well as gear to rent.
Multiple times a day there's the opportunity to explore below the surface. We give you tips and tricks for releasing the inner mermaid and merman in you.
One our personal highlights of Caribbean exploration. Finding, chopping and zipping coconuts! It gives us the superpowers to keep going.
IMPACT | We share adventure and relaxation time, as well as thoughts, tips and ideas about how we can live more simply and sustainably, whilst exploring the natural world. No one of us has the answer, but together we do have. Connection and conversation at sea go deeper in one day than months on land.
LOCAL | We aim to team up as much with locals to learn the best we can about the local situation. Working with a local partner comes with different habits, customs, awareness levels and cultural backgrounds. We stay open and look beyond our ‘eco-bubble’ to plot better routes for positive change.
GETTING THERE | We are aware that many need to fly to join one of our trips, and encourage transport options such as train, bus, ferry and car sharing. We’re actively looking for the best ways to maximize our positive and minimize our negative impact. We recommend booking only one way ticket. You won’t be the first ocean nomads joining a trip, and just keep on going…
ENVIRONMENT | We do what we can to minimize our environmental impact. We sail as much as we can and use the motor as little as possible. Preparation and doing your part is key. And we encourage and welcome your ideas, tools and tricks on improving our positive footprint.
PROVISIONING | Collectively we take care of the provisioning and cooking. It’s part of the fun! We don’t organize luxury cruises. We aim to provision as locally as possible, and minimize plastic use. Our trips are vegetarian (fish and meat-free), with occasional opportunities to eat ashore if you struggle with this. We use less freshwater and power than the average sailboat charter. We share thoughts, ideas, and knowledge on no-fridge food preservation, eco-friendly sailboat maintenance, and other positive solutions.
OCEAN PROTECTION Our drive: Protecting our playground!
PEOPLE | We make our gathering big enough to guarantee a wonderful mix of inspiring souls, but small enough to drop anchor in the middle of nature. Participants usually don’t know each other, but after days of shared adventure and collaboration, new friendships are made. Many of our previous nomads come back again and again. Ocean Nomads come from all walks of life; we put a lot of effort in creating a diverse mix of people, so that we can learn from each other and pass on inspiration & ideas. Many trip alumni and members have since teamed up for more adventure and impact projects. All ages are welcome and encouraged to join. Reasons for joining are often the desire to live a nomadic lifestyle, buy a boat, share experience, and learn with safety, sustainability and accessibility aspects being taking care of.
TEAMWORK | Sailing is an active way of travel that needs teamwork. We share the tasks, operation, and sailing of the boat. We provision, cook, sail, fix things (if necessary) together as a team. Our trips are not a laid back luxury experience.
Hands-on participation creates the adventure, and helps you learn to be a better sailor. That said, for all our Caribbean trips we already have enough hands on board so you are welcome to sit back and relax if that's what you're after!
HEALTH | We can only do good if we feel good. Our trips have elements of yoga, breathwork / freedive / kitesurf clinics, healthy and local food provisioning, and lots of outdoor action and adventure. Powered by YOU, our members and crew.
PEACE | Our trips are not a party experience. We value the mornings and like to maximize daylight for exploring and connecting to nature. Drinking a lot of alcohol ruins this experience and has no place on our trips. We operate a strict no alcohol at sea policy. On anchor or on shore no problem. We like an sunset beer or wine now and then too.
ADAPTATION | Boats rock and make noise. Boats are small. People snore. Weather rules. We have limited resources. Adaptability is key. That said, SV Twister is the most luxurious vessel we ever teamed up with.
ACCESSIBILITY | Any age, gender, and experience level is welcome. We know a trip like this is not within financial reach for everyone. It costs considerable money to make this expedition real, in most safe way. But where resources allow we facilitate scholarship opportunities to make an adventure like this accessible for the driven on a budget ones.
Learning by doing, that’s what we strive for. Here are some of the skills you develop on our trips:
SAILING | You’ll learn hands-on everything to become a competent crew member. By the end of the journey you can sail the ship. Our skippers and often also fellow crew members are happy to share and show what to know.
SEAMANSHIP | Huge part of happy, safe and meaningful ocean nomadic living depends on your seamanship skills. You can have the biggest bank account but once you’re at sea nothing can be googled or bought. And no person can be hired to fix something. You have to be inventive as situations arise and you’ll learn from experiences along the way. You’ll learn to work with your hands. Especially on our offshore trips, you learn about the wind, the weather, geography, stars, navigation, sea life, boats, yourself, people, and much more.
CONSCIOUS LIVING | Experience resourcefulness. And how you can implement it all into your life. As sailors, we are intricately connected to the ocean on a daily basis. Experiencing sea time daily provides a deep and lasting respect for nature. You’re dependent on it. You experience the power of the wind and the waves, and realise how precious our resources are, such as water, fresh air, power, and fresh vegetables. You will become aware that what might be considered normal ‘back home’, is not so normal on a boat.
NATURE AWARENESS| Most of us spend more time indoors than outdoors. It’s easy to forget the natural world we’re coming from and living in. On the ocean, you face the wind and water elements and find that connection to nature. Imagine a scene with no traffic, no news, no pollution, no civilisation. Just wind and water – plenty of that! A scene where you can gaze for hours to the millions of stars above you; enjoy the dozens of dolphins sliding through the water at the bow of the boat; admire the pink-orange-red sunrises and sunsets, without any airplane trails changing the fluffy and cauliflower-like cloud patterns.
By being disconnected from everything but nature, you’ll learn a great deal about the ocean. When you see the good, bad and ugly with your own eyes, talk face-to-face with people living on and for the ocean, and experience its value, it makes you eager to learn more, do more, be more, and likely Live more: At sea.
You’ll become very aware of the natural world around you. This inspires. And it’s eye-opening. You come to realise how disconnected from nature we are in our daily lives. In the middle of nature, far away from civilisation, you will see human impact. Usually we’re far away. It’s hard to make it tangible. It doesn’t really affect us. Or so we think. But by being out there, you literally broaden your horizon. Experience will make you think, gain fresh perspectives, and may inspire you to act to turn the tide of the ocean challenges.
We share tips & tools, helping accelerate personal journeys to alternative adventurous conscious life on or near the sea. Ocean nomads adventures are not just a one time thing you join for a week or two and that’s it. These are experiences that change the way you approach life, nature and the ocean. We believe our trips are just the beginning for plotting the next course in your life. By jumping on board this, you also join our expanding global network of impact-driven travellers, ocean entrepreneurs, sailors, (free)divers, surfers, and active salty souls passionate about the ocean and eager to do good.
On our community HUB we continue the conversation, action, team-ups and meet-ups beyond our events and expeditions to maximize the impact, fun, and ripple effects for ocean adventure and action. We got your back before and after the trip and make the personal connections and introductions to accelerate your dreams.
We used to have an image in our head that sailing is only for rich people, that it’s about showing off boats and boat toys, and that as crew you’re just meant to scrub the deck. Not true. Sailors are free spirits and ocean-minded people. Most of us share the same dream to live a simple life on a sailboat, set off to explore the world, and live life on their own terms. We unite and exchanges ideas to make this dream happen! We connect with fellow nomads that are on the same mission. Who knows who you may meet during these adventures and what opportunities may come from it?
The last day we definitely recommend a sunrise wake-up! A jump in the sea. Perhaps a last snorkel or freedive session. We have a last breakfast (for now) together. We drop you off at the shore and then until we sea each other again:)
This is not just an expedition you join for2 weeks and that’s it. This is an experience that will change the way you approach life, nature and the ocean. We believe our ON expeditions are just the beginning for plotting the next course in your life. By jumping on board this voyage, you will also join our expanding global network of impact-driven travellers, ocean entrepreneurs, sailors, (free)divers, surfers, and active salty souls passionate about the ocean and eager to do good. On our community platform we continue the conversation, action, team-ups and meet-ups beyond our events and expeditions to maximize the impact, fun, and ripple effects for ocean adventure and action. We got your back on this expedition and the journey after.
