Who We Are

We care more about how we move through the world than where we end up.

On a sailboat you feel the line between what you can control and what you cannot more keenly. Life at sea can be humbling, and our personal limits are tested by our knowledge, the weather, timing and those on board.

Sailing reminds us that forward motion comes from adjusting ourselves to the conditions, not imposing ourselves on them.

1. Participation
Everyone is encouraged to take part in life on board at a level that fits their interests and experience.

2. Learning by doing
We build skill and confidence by exploring, trying new roles and learning through participation.

3. Connection and straight talk
Shared tasks and shared conditions build camaraderie. Life on board is sometimes challenging, so honest, calm communication and looking out for each other matters.

4. Respect for sea, boat and place
We treat the sea, the vessel and local communities with care. Weather and conditions set real limits, and we plan and act within them.

5. Responsibility
We expect each person to own their attitude and choices, and to do their part. Safety and good seamanship depend on that.

6. Homecoming
We go out to sea and return with a clearer sense of what matters, and a handful of experiences to carry with us.

SailDeep began with a simple question: what if a trip to the Caribbean was less about passive luxury and more about taking part?

The idea took shape in Barbados, an island surrounded by the Atlantic Ocean. Its founder had spent years in commercial photography and noticed the same pattern in himself and others. Life indoors, on screens and on the clock, left people tired and overstimulated. Time outside, doing real physical tasks and stepping out of their comfort zone, left them steadier and more alive.

In 2024 he bought Nayru, a 36 foot Beneteau Oceanis, refitted her in Trinidad and sailed her back to Barbados. That first return to the island after days offshore fixed the core of the brand. SailDeep would not be about ticking off sights. It would be about small groups, shared experience and the quiet satisfaction of testing yourself and coming back ashore.

SailDeep now runs voyages from single-day passages to ten-day liveaboards. Every trip follows the same principles: no more than four guests, everyone taking part at a level that fits their interest and ability, routes shaped by conditions rather than wish lists, and a clear sense of what can be controlled and what cannot. Diving can be part of the picture, but sailing and sea life are the foundation.

SailDeep exists for people who aren’t interested in skimming the surface and want to see what they’re capable of.

The mission is straightforward: to give small groups a real, open-ended adventure on the water.

If you feel pulled toward that kind of experience and want to find out how it feels to live aboard, SailDeep is an invitation to step onto a sailboat, share the adventure and see what the horizon has in store.