Sailing Family Sails into Big Seas: Did We Make a MISTAKE?
Welcome back to Finding Our Isla.
In Season 1, Episode 5, we leave Saline Bay and continue sailing north toward Bequia — still without a working steering cable.
As we push forward, we sail straight into the powerful Caribbean Christmas Winds and battle rough seas, strong winds, and multiple squalls along the way.
During the passage, the kids begin getting sick. At the time, we thought it was severe seasickness caused by the rough conditions… but we would later discover it was something much worse.
After a challenging sail, we finally arrive in beautiful Bequia where we restock the boat, explore the island, and continue adjusting to life as a full-time sailing family.
From provisioning across multiple local shops to tackling boat repairs and preparing for the next passage north, this episode captures the reality of learning to sail while living aboard full time in the Caribbean.
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Finding Our Isla Sailing
We’re a family of five who left traditional life and moved full-time onto our sailboat, Isla. This channel shares the real side of family boat life. What it actually costs, how we homeschool while traveling, the challenges no one talks about, and the moments that make it all worth it. We live aboard full-time in the Caribbean and document life afloat with kids: • the finances behind this lifestyle • daily routines and homeschooling on the water • the hard days, the growth, and the joy • choosing time, connection, and freedom over stuff No highlight reels (okay... maybe a few) No pretending it’s perfect. Just honest life on the water. If you’ve ever wondered what it takes to make a big life change... or you’re dreaming of a different way to live, you’re in the right place. 🌊 Full sails. Full hearts. Full-time family life.
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