Trip to Port Protection Alaska | First Time, Freight Run & Boat Life

Boat life in Alaska has a way of turning a simple trip into something much bigger. We headed into Wrangell to pick up Audrey’s daughter Ada at the airport as she came to join us aboard the Alaskan Gypsy. What should’ve been a quick turnaround turned into a full freight run, loading roofing metal, plywood, screws, and supplies for friends and projects out in Port Protection… along with 300 more gallons of fuel for the boat. That’s how it works out here. If you’ve got the boat, you move what people need. One trip turns into helping a handful of people without really planning it that way. We left town late in the day with the deck stacked and daylight fading, the Coast Guard running training nearby, and weather building in Sumner Strait. Out here, you’re always weighing your options… when to go, when to wait, and when to find shelter. One of those decisions brought us into Roosevelt Harbor, tucked in behind Rumble Island. Snow on the beach, glassy calm water, and total quiet after a rough stretch outside. The kind of anchorage that makes you exhale the second you’re inside. From there, we continued on to Port Protection. This trip was also a first… for Ada. Her first time coming out here, seeing what life actually looks like in a place like this. The dock, the float planes, the timing of everything, and especially the store. The Port Protection store is one of those places that tells the whole story of remote Alaska without needing to explain it. Groceries, random essentials, fishing gear, snacks, things you didn’t expect to find and things you’re really glad are there. When the plane comes in, everyone moves. Mail, food, supplies… it all passes through that dock and into people’s hands in a small window of time. We spent time walking through, picking things out, laughing, and just taking it all in. It’s simple, but it’s also everything. That store, that dock, that system… it’s how life happens out here. This video is a mix of hauling freight, making weather calls, finding shelter, and getting a real look at what it means to travel and live by boat in coastal Alaska. And for us, it’s also about sharing this life as it unfolds… one trip at a time. ⏱️ CHAPTERS 00:00 Boat Life + Loading Freight 00:04 Hauling Roofing Metal & Supplies 00:52 Why a Bigger Boat Changes Everything 01:36 Picking Up Ada in Wrangell 01:55 Loading Fuel, Materials & Final Prep 02:26 Coast Guard Nearby 03:38 Leaving Town with a Full Deck 04:02 Airport Pickup & Wrangell Errands 05:05 Coast Guard Training Activity 05:23 Productive Day in Town 06:05 Getting Underway 06:46 Meet Ada Aboard the Gypsy 07:30 Checking In with the Captain 08:11 Riding the Tide Out 09:21 Sailing Into the Sunset 10:13 Weather Building Near Sumner Strait 11:09 Changing Plans & Looking for Shelter 12:45 Entering Roosevelt Harbor (Narrow Approach) 16:50 Anchored & Settled for the Night 18:06 Snow, Silence & Anchorage Life 19:06 Paddleboarding with Ada 20:55 Winter Boating Reflections 21:12 Why This Life Feels Special 25:09 Sailing Moments Together 25:50 Arriving Into Port Protection 27:05 Exploring the Floating Dock 28:12 Inside the Port Protection Store 31:56 Visiting Friends & Community 32:11 Float Plane Arrival & Dock Activity 33:12 Spring Break Time Aboard the Gypsy