Day 1 — Racing the Clock: Crossing the Gulf of Alaska in Winter

Day 1 of our 18-day countdown begins. It’s December 1st, and we’re still in Wrangell, Alaska, working nonstop to get the Alaskan Gypsy—our steel-hulled schooner—ready for a winter journey north. Our deadline? December 18th, when we pick up all five kids for Christmas break. We’re trying to get this boat from Southeast Alaska to Prince William Sound, which means traveling the entire Inside Passage and crossing the Gulf of Alaska in winter, one of the most notorious stretches of water known. The systems list is long: • Hydraulics acting up (no anchor without it) • Heater struggles in freezing weather • Water tank repairs • Minimal fuel on board • Deck still cluttered from shipyard • Radar issues • Autopilot not working • Endless little projects stacking up And yet… we’re moving forward. Sea trials, repairs, late nights, early mornings — whatever it takes. This trip isn’t just about the boat. It’s about family, Christmas, grief, healing, and starting a new chapter aboard a vessel that can finally fit all of us. It’s our first Christmas without Audrey’s brother, and getting to Prince William Sound matters in ways beyond words. Will we make it north in time? Will the weather cooperate? Can the Alaskan Gypsy handle a winter crossing? We’re sharing this 18-day journey in real time — mini updates, long-form videos, and regular live streams as we work toward Whittier and the family waiting on the other side. Subscribe and hit the notification bell if you want to follow along. And join us tonight for our LIVE update from the wheelhouse — we’ll answer questions and talk honestly about what Day 1 has felt like. Thank you for being here. ❤️ — Audrey & Scott Alaskan Gypsy Life ⭐️ CHAPTERS 00:00 — Rolling live in the wheelhouse 00:14 — Day 1: December 1st 00:55 — Sea trials + mixed results 01:38 — Hydraulics + anchor issues 02:07 — Heater, water tank, fuel 02:23 — Deck chaos + shipyard leftovers 02:30 — Autopilot + radar problems 02:41 — Why the deadline matters 02:54 — The December 18 pickup 03:10 — The route: Wrangell to Whittier 03:45 — Winter Gulf of Alaska realities 04:10 — Kids, family, and Christmas 05:00 — Emotional weight of this year 05:45 — Can we make it in time? 06:00 — Sea trials + shrimp boat friend 06:50 — Endless tasks + flow mindset 07:20 — This journey begins…