
Hawaii to Alaska — Selling Everything and Going Sailing
It’s the classic story of selling everything we owned to begin our adventure. My wife and I purchased SV ‘Iwa, a ’99 Beneteau 47, through Atomic Tuna in spring 2021 in Sausalito. We moved aboard and spent a month prepping the boat in Emery Cove Marina. We pushed off the dock to begin our trip south to set up for a trade-wind passage to our home in Hawaii. Once back home, we would continue to work and fit our bare-bones boat to a liveaboard full-time cruising bluewater boat.
The trip down the coast was a classic coastal hop including lots of firsts for both my wife, Heid, and me. She had minimal sailing experience, learning to sail on Lasers and Toppers just months earlier. I had a bit more, having sailed and owned smaller sailboats for the past 20 years and made a couple of deliveries as crew from Hawaii to L.A. Our first passage took 17 days with just the two of us from San Diego to Hilo, Hawaii. We spent the following two years sailing and exploring the Hawaiian Islands from Hilo to Hanalei and back. All the while we were learning our boat and constantly improving her as we got prepared to finally leave our home and set off over the horizon most of us dream about.
We had our sights set on summer 2023 to point the bow north. The comfortable cruising season in Alaska is short: June to August/September is when you make most of your miles before the wind starts to bite a little deeper and the gloves get a little thicker. We intended to follow the classic route of making our way due north to the Gulf of Alaska and the Inside Passage, where we would winter over in Juneau. Early the next season, we’d get a jump on the Inside Passage, making our way south to Mexico.

The passage north is more complicated than any other that I have done before. It involves multiple weather patterns and, of course, the cold. Even in the summer, the Gulf of Alaska can get chilly, and coming from the tropical warm waters of Hawaii to the cold gray seas of Alaska is a drastic change.