We Left Our Boat for ONE DAY… What Could Go Wrong?

Living aboard an 80-foot sailboat in remote Southeast Alaska means even a road trip starts with a skiff ride. We left Alaskan Gypsy anchored in Port Protection and joined our friend Liz for our first drive across Prince of Wales Island, home to what we’re told is the longest road in Southeast Alaska. The plan sounded simple: drive to Thorne Bay, get some supplies, look at a small barge for a friend, and make it back to Gypsy that evening. Then came the flat tire. Along the way we encountered deer, black bears, miles of gravel road, some eye-opening remote Alaska grocery prices, a questionable amount of cheesecake, and plenty of ridiculousness packed into a tiny car. But the strangest part happened after dark. We returned to the shoreline at low tide only to discover the paddleboard we had left there, our only easy way of reaching the skiff tied offshore, completely flat with what appeared to be a deliberate puncture. Just another straightforward day in the Alaskan Gypsy Life. Come along as we explore Prince of Wales Island by road for the first time and discover that sometimes getting off the boat creates an entirely different kind of adventure. #alaska #princeofwalesisland #remotealaska #alaskangypsylife #roadtrip Chapters: 00:00 Leaving Gypsy for a Road Trip 00:29 Every Road Trip Starts With a Skiff Ride 03:00 Getting Ashore in Port Protection 04:38 Road Tripping With Liz 05:18 Our First Flat Tire 08:03 Back on the Road 08:18 The Washouts Get Interesting 09:31 We Made It to Thorne Bay 10:18 Remote Alaska Grocery Prices 11:45 Scott Found Us a New Boat?! 12:29 Inspecting a Barge for a Friend 14:50 Scott Discovers Highways 15:46 The Longest Road in Southeast Alaska 18:03 81 Miles Back to Gypsy 19:04 Apparently Audrey Is Famous 😂 22:18 An Incredible Alaska Sunset 23:00 Things Get Weird in the Car 27:23 Will the Tire Make It Back? 28:48 Back at the Hangover 29:55 We Might Have a Problem 30:40 Something Happened to Our Paddleboard 31:49 We’ve Got a Situation 32:12 Was the Paddleboard Slashed? 32:51 Getting Back to Gypsy in the Dark 33:19 We Made It Home 34:11 But There’s One More Story… 35:41 Our Only Way Back to the Skiff Was Flat 36:26 This Wasn’t a Bear 37:39 Who Would Do This? 40:26 This Could Have Been Dangerous 42:19 The End of a Very Strange Adventure