What “Going to Town” Really Looks Like in Remote Alaska

After a week of work in Port Protection, it was time to make the run back toward town… whether we felt like it or not. This is what that actually looks like for us. An early departure to stay ahead of weather. Picking our way around the northwest tip of Prince of Wales Island. Waiting on current and wind in Merrifield Bay. Motor sailing when we can. Sailing when it makes sense. And a whole lot of watching conditions evolve in real time. Nothing dramatic on this trip. Just winter boating in Alaska and the steady, time-intensive reality of moving a 110,000-pound boat through Southeast Alaska when you live off the road system. Along the way: • Working the weather windows • Killing time while tide and wind sort themselves out • A brief overboard rug incident 😅 • Fresh pumpkin chocolate chip cookies in the galley • Hunting for a safe overnight anchorage • Catching what wind we can in Sumner Strait • Making steady miles toward Wrangell By the end of the run, we’d been on our way to town for over a full day, reminded again that out here, even simple logistics take planning, patience, and a willingness to move with the conditions. If you’ve ever wondered what everyday boat life really looks like in remote Alaska, this is it. No staging. No scripts. Just the rhythm of life aboard the Alaskan Gypsy. ⚓ Vessel: Alaskan Gypsy 📍 Southeast Alaska 🌊 Living and working full time aboard Subscribe for real working waterfront life, remote cruising, and honest day-to-day life afloat. Chapters: 00:00 Leaving Port Protection 03:01 Why We’re Headed Back Toward Town 04:59 Early Winter Morning Underway 05:22 Rounding Prince of Wales Island 06:52 Picking Our Way Around Point Baker 08:10 Waiting on Current in Merrifield Bay 11:56 Watching Conditions Settle 13:34 The Rug Overboard Moment 14:58 Why We Stayed Put 17:02 Killing Time and Boat Projects 18:05 Fresh Pumpkin Cookies in the Galley 19:08 Working From the Mobile Office 24:40 Trying to Catch Some Wind 25:20 Searching for a Safe Anchorage 27:03 Evaluating the Anchorage 31:07 Night Sounds on the Gypsy 35:19 Morning Departure and Plans 36:02 Checking the Wind Again 37:20 Raising the Sails 43:33 Under Sail in Sumner Strait 45:31 Finally Making Miles 49:13 27 Hours Into the Trip 51:20 Motor Sailing the Gypsy 53:26 Midday Wheelhouse Update