How it Works
Our crew is carefully selected to ensure a supportive and transformational experience.
- Reserve Your Spot → Pick an expedition and pay a fully refundable $500 deposit to show you’re serious.
- Interview → Schedule a short call with our captain to make sure it’s a good fit both ways.
- Join the Crew → If accepted, your deposit is applied to your expedition balance.
Every expedition is different. Some are mellow island hops. Others are multi-day ocean crossings. All of them push you to grow — and reward you with raw moments, tight-knit crew bonds, and the kind of confidence that only comes from doing something real.
🌊What we offer
Train
Adventure
Adventure
Learn more than just how to sail — gain the knowledge, skills, and experience to be COMPETENT. Sailing shouldn't be stressful or scary. It should be fun for you and the people around you.
Our training is hands-on, full immersion, and NauticEd-certified. Earn Certificates, Licenses, & Endorsements that allow you to charter boats anywhere in the world.
Adventure
Adventure
Adventure
The sea isn’t just a place we cross — it’s where we play, train, and test ourselves.
Between landfalls and night watches, we chase surf, ride foils, and dive deep.
Every day brings a new kind of challenge — and a new way to feel alive.
Explore
Adventure
Explore
Some of the best places on Earth can only be reached by boat. There’s a good chance you haven’t even heard of your next favorite place —and an even better chance you’ll discover it as part our crew. Our expeditions actually go somewhere—no round trips, no fixed base, just real adventure. We go where the wind takes us.
⚓️ Why We Sail This Way
We don’t sail this way because it’s easy. We sail this way because it’s honest — and it works.
At sea, there’s no pretending. Just wind, weather, and how you respond. Discomfort becomes clarity. Challenge becomes growth.
Our expeditions are built around continuous exploration and the idea of Misogi — doing at least one hard thing each year that truly tests you. We help each crew member identify and attempt their own Misogi. Whether it’s learning celestial nav, leading a night watch, paddling into your first wave, or just showing up scared but willing to do your first deep freedive — we’ve got your back.
On SV Indie Sky we don’t follow fixed routes. We rarely return to the same place we left from. Wind, weather, and instinct shape our course — not schedules. You may not know exactly where or when you get on or off the boat. For most people, that kind of unknown is too much. But for those who can handle it, it’s life-changing. It forces you to let go of control. To stay present. To listen to the ocean. And connect with the natural world in a way most modern people never experience.
You’ll reach places only accessible by boat — and you’ll be changed by the process: night watches under stars, trimming sails for performance, fixing what breaks, and staying calm when plans fall apart. And the challenge doesn’t end on deck. We surf reef breaks. We foil between islands. We free-dive wrecks. This is Misogi in motion — on the boat and in the water.
We don’t just design challenges — we support them.
You don’t grow by coasting. You grow by showing up, taking risk, and finding out what you’re made of.
We don’t offer vacations. We offer transformation — powered by wind, salt, and intention.
Our Partners
