First Time Sailing Alaskan Gypsy… Alone

There’s something about a rare sunny day in Southeast Alaska that messes with your head. The wind was blowing 5–7 knots. Straight downwind. And Alaskan Gypsy has five sails that haven’t been raised in years. Audrey was on her way back from Anchorage. The new rigging lines haven’t arrived. The old lines are mossy. There are loose parts on deck. And I’m alone. Probably not the “responsible” time to try sailing her for the first time. But sometimes you don’t wait for perfect. You just raise the sail. This is the first time Alaskan Gypsy has sailed since we’ve owned her (and probably the last 20 years or so!!). Engine off. Quiet. Just wind and canvas. And I have a feeling this is the beginning of a whole new chapter. Welcome to the sailing chapter. — Scott #AlaskanGypsy #FirstSail #LiveaboardLife #SailingAlaska #SelfReliant ⸻ 📚 Chapters 00:00 Wheelhouse chaos & rainy mindset 02:40 The sun finally shows up 03:45 Downwind breeze temptation 04:50 Should I sail her alone? 06:20 Inspecting old rigging lines 09:00 Loose parts & self-doubt 12:30 The obsession begins 15:00 Engine off… sail up 16:00 Moving under sail 18:30 “I’m a sailor now” 20:20 Calling Audrey 22:45 Sea lion welcome committee 24:00 What this moment means