Water wisdom
Santa Barbara, California
The Crossing
Multi-Day Sailing Voyages · Next Voyage: TBA
Immersive multi-day sailing voyages between Santa Barbara and the Channel Islands for you and a small group of soulful and curious men, connecting with water in ways that will invite you to go beyond the self you know.
Water teaches by example.
Water Wisdom offers experiences in, on, and with water to deepen our relationship to ourselves, to others, and to the natural world. The Crossing is our flagship offering: a multi-day sailing rite of passage with a hand-picked group of men, where the ocean and authentic relating set the curriculum, and where meeting our edges, opening to the unknown, and cultivating honest fellowship are the journey.
Water has taught humans for as long as people have seen rain fall from the sky, have gone to sea, drank from a spring, or sat quietly at the edge of a river. While water is essential to life and supports us, it doesn’t perform for us or flatter us. But if we allow it, water can teach us by example how and when to be soft and when to be powerful, when to be agile and resilient, insulating and transmitting, transparent and impenetrable, ephemeral and eternal, and always life affirming.
The Crossing is not a wellness retreat with an ocean backdrop, it is a deep exploration with the ocean and the physical characteristics of water — fluidity, clarity, force, vitality, connectivity — experienced and felt in your body, crossing over into your consciousness, and then carried home as something you understand differently, both about yourself and the greater world.
With no prior experience necessary, and lead by a seasoned captain and deeply intuitive facilitator, you will share in the challenge and reward of navigating and sailing a 42-ft offshore cruising yacht, free-diving kelp-forested rocky reefs, communing through aquatic somatic practices, and coexisting in the shared, intimate space of a sailboat with a small group of fellow men for days at sea. Unplugged from technology, held by the vastness of the endless blue, you are seen and supported by tribe as you safely lift anchor from your daily life, dive headfirst through your thresholds, and take space to hear the whispers of your heart’s longing. This is an opportunity to challenge and empower yourself as you renew your relationship with water, such that you come home with an enlivened and revered relationship with yourself, your fellow man, and with life.
Water is Life.
If we stay open to it, the physical attributes of water teach us how to live life. The Crossing attunes to five characteristics of water, not as loose metaphors, but as a map for the curated activities you will experience, embodying these properties and seeing the relevance in your own life.
Fluidity
Water takes the shape of what holds it, moves around what’s in its way, intuitively finds the opening, takes the most available path, and fills the empty space.
Clarity
Water’s state of being will determine what is seen and felt. Still water mirrors what’s above and reveals what’s below, though force disturbs it, clarity always returns.
Force
Water is immensely powerful in its volume, movement, and persistence, continuously asking when to effort and when to surrender.
Vitality
Water is both essential to life and nourishing, is a medium for life, and is forever cleansing, refreshing, and renewing.
Connectivity
Every drop is part of one cycle — rain, river, ocean, vapor, rain again — receiving, transmitting, and buffering the energy of those around it.
“You don’t learn to trust the water by thinking about it differently. You learn by floating, and noticing that you didn’t sink.”
— Water Wisdom
What This Actually Looks Like
Six moments from the days at sea.
Hands on the Sails
Actively sailing and navigating the boat with instruction from a licensed captain.
Island Kayaking
Kayaking to and from shore, with time to explore.
Kelp Forest Snorkel
Swimming through kelp forests thriving with life, starting with snorkel and free-diving instruction.
Shallow Water and Onshore Activities
Inviting in and embodying water’s wisdom through group and individual activities.
Communing
Coexisting, collaborating, and encouraging your fellow men.
Sleeping and stargazing at Anchor
Decompressing to some of the quietest and darkest nights found in Southern California.
Photography via Pexels, used under the Pexels License.
Meet Your Water Guide
Michael Sheehy
Marine biologist, aquatic somatic practitioner, and facilitator — guiding you through water’s lessons.
In Their Words
“
Michael has combined a deep dive into watery nature, which brings everyone to an edge, and then with deep authenticity and compassion, guides you into a soul-revealing journey.
— D.L., The Crossing, August 28–30, 2026
“
This voyage allowed me to find my edge and listen in a way that is a rare encounter in my day-to-day. I enjoyed this container for the richness of connection and the aliveness of the environment. This was my first time on a sailboat and a worthwhile adventure! Thank you, Michael
— L.S., The Crossing, August 28–30, 2026
“
Michael creates incredible experiences of connection and inner exploration while testing your edges in one of the most beautiful environments in the world. Michael is truly admirable, with life-long pursuits of depth, he leads with authenticity and vulnerability and orchestrates an environment that feels safe to explore and share in a way that is entirely unique. We were able to speak to feelings that are rarely expressed and feel the comradery of common emotions. The trip particularly made an impact on me to find strength through vulnerability. With great respect, thank you Michael for your passion and efforts to share this meaningful connective energy with others.
— S.M., The Crossing, August 28–30, 2026
Plan Your Crossing
Next Voyage
To Be Announced
Dates for our next multi-day voyage are coming soon. Reach out and we’ll let you know as soon as they’re set.
Voyages depart from and return to the Santa Barbara or Ventura. Specific dates, arrival and return times, and logistics are shared with each announced voyage, including the option for those coming from out of town to arrive the night before and stay aboard at the slip.
What’s Included
- Multiple days and nights aboard a 42′ sailboat with a small group of participants
- All meals and snacks while aboard
- Kayaks
- Facilitated practices and excursions tied to the five water characteristics
- Sailing and snorkeling instruction by an experienced captain and water guide.
What to Bring
- Layered warm clothing , rain coat— Channel evenings run cool, even in summer, crossing can be cold and wet
- Sneakers for hiking
- footwear that can get wet (can be same as snorkel booties)
- Sunscreen, sunglasses, sun-protective clothing, a hat
- A journal, writing impliment
- Swimsuit, and quick-dry towel
- Your seasickness remedy of choice
- Snorkel equipment: Mask, snorkel, fins, weight belt, weight, booties, neoprene hood, and at least a 4/3 wetsuit. We can help you rent any or all items if needed.
Frequently Asked Questions
Do I need sailing experience?
No. This voyage is designed for the general public, not experienced sailors. You are the crew — our experienced captain and first mate safely instruct and guide every task in the moment, no prior experience required.
Is this a wellness retreat, or a sailing trip?
Both, inseparably. Participants are invited and guided to experience the sailing and the time in, on, and with the water differently then perhaps they would on a recreational trip.
What if the weather changes the plan?
It might, and that’s part of the design. Anchorages and routes in the Channel Islands shift with wind and swell. When our captain makes a real-time call, we treat it as a live lesson in adaptability rather than hiding it as logistics.
I get seasick easily. Is this trip for me?
Talk with us before booking. The Santa Barbara Channel can have swell, especially on the crossings. Many guests sail comfortably with over-the-counter or prescribed remedies — we can advise based on your experience.
Where do we sleep, and what are the accommodations like?
You’ll sleep aboard the vessel at anchor each night in shared cabin berths. This is a working sailboat, not a cruise ship — comfortable, but intimate.
How physically demanding is the voyage?
Moderate. You’ll hike, kayak, snorkel, and help handle lines and sails. No specific fitness level is required, but you should be comfortable being active outdoors for a full day and swimming in open water.
The Crossing is waiting.
Spaces on each voyage are limited to keep the group small and the water close. Reach out to be among the first to hear when the next voyage is announced.