Q&A - What’s Next on Our Liveaboard Sailboat?

We’re sitting down in the wheelhouse of Alaskan Gypsy, our 80-foot steel, triple-masted motor sailer, to answer your comments and talk honestly about what’s next. After a major hull restoration, time in the shipyard, winter storms, and settling back into harbor life in Wrangell, Alaska, we’re entering a new phase: a four-season liveaboard lifestyle in Southeast Alaska. This video is a follow-up to our recent “What’s Next?” post and is part update, part reflection, and part open conversation with this community. We talk about: -Living full-time on a large sailboat in Alaska -Leaving the shipyard after major hull work -Boat life vs house life -Work, income, and creative ways to support a liveaboard lifestyle -Freight hauling, self-employment, and remote work ideas -Physical limits, pacing yourself, and sustainability -Kids, family, and education while living unconventionally -Why we chose this boat and this life If you’re curious about boat life, off-grid living, sailing in Alaska, or what it really takes to live aboard year-round, this one’s for you. Thanks for being here and for all the thoughtful comments. We’re reading them… just not always replying with our thumbs 😉 👉 Subscribe to follow the journey 👉 Drop a comment — we really do read them ⏱️ CHAPTERS 00:00 – Welcome & Why We’re Making This Video 01:30 – What’s Changed Since the Shipyard 03:40 – Living Aboard an 80ft Sailboat in Alaska 06:00 – Four-Season Liveaboard Lifestyle 09:30 – Work, Income & Self-Employment on a Boat 13:45 – Physical Limits, Health & Sustainability 17:30 – Freight, Remote Work & Boat-Based Ideas 22:30 – Kids, Family & Education While Living Aboard 25:30 – Passenger Trips, Retreats & Why We’re Careful 28:30 – Why We Chose This Boat & This Life 31:00 – Final Thoughts & Community Reflections