Sailing from Hawaiʻi to Alaska: A Dream Come True
Community
Mar 1, 2026

If Not Now, Then When?
Meet Christy and Dave. They are originally from New Jersey and have known each other since they were twelve years old. They've always talked about sailing around the world. It felt unrealistic at the time, but the dream stuck. Money was a big factor. They had gone through different phases of life together, but the dream never changed! Eventually, it reached a point where they asked themselves, if not now, then when?
They lived aboard a Catalina 34 for a couple of years, cruising around the Hawaiian archipelago. But over time, and after bringing their dog Porter aboard, the boat began to feel small. So they upgraded to a 2007 Tayana Vancouver 460 Pilot House. And every time they take her offshore, it still feels surreal that she’s theirs.

This Is Only The Beginning
Over the years, their purpose has evolved. At first, it was simply about getting out on the water. Then they caught the cruising bug and decided they wanted to sail to the South Pacific, the Marquesas were always on the list. Now, the goal has expanded to a full circumnavigation.
Sailing from Hawaiʻi to Alaska aboard their own boat made one thing clear: this is only the beginning.
Excerpt from their digital logbook:
"We freakin’ made it. After almost three weeks at sea, we’re finally tied up in Sitka, Alaska, with a cold beer in hand and the boat finally at rest. It feels surreal to say the crossing from Hawaiʻi is behind us after anticipating the journey for so long. In the moment, the days felt long, and I came to the obvious realization that the Pacific Ocean is, in fact, really big 😂.Still, the days passed like the wind. The crossing was relatively mild and, although frustrating at points, filled with moments that reminded us why we were out there in the first place. Sailing in Hawaiʻi prepared us in ways we didn’t fully appreciate until we left. It’s where we’ve grown as sailors and people over the past decade, shaped by the islands’ generally unforgiving conditions. The sailing was rarely easy, and often pretty unfriendly, but it taught us how to stay sharp, adjust expectations, and how to accept when nature has the final say. We weren’t sure if Hawaiʻi was just a tough place to cruise or if we were still green to the ‘cruising life’, but it was probably both.
Leaving was hard, but we knew it was time. The first few days offshore were rough. The trades were vindictive; it felt at times like the islands were trying to keep us from leaving. We beat into the wind straight out of the gate for nearly a week. The seas were big at first, then settled into a more manageable size, but still squarely on the beam, making things uncomfortably rolly and sleep scarce.
Eventually, we broke free and found lighter air west of the North Pacific High. It felt like we were no longer fighting with the boat, but sailing with her. We exhaled for the first time in a week. The gennaker went up and we had a calm, steady run north for several days. It was such a relief after all the pounding and trimming and second-guessing.
Then we hit the so-called westerlies. And of course, they weren’t westerlies. Once again, we were nose to the wind, slogging through more upwind sailing. A high-pressure ridge built in behind a cold front, flipping the winds from southwesterlies to northeasterlies and blowing us days off the rhumb line. The wind gods were absolutely not on our side. When we finally broke through, the real westerlies arrived, but they were light. Still, we managed one-and-a-half glorious days of fast and slightly chaotic downwind sailing. Big seas from a low pressure system rolled beneath us as we surfed along, finally moving the way we should have been. Then, the wind faded again, and we made the call to motor-sail hard northeast to stay ahead of the next low lining up for the coast.
In the final stretch, the wind hovered between 10 and 15 knots at 90 to 120 degrees apparent. We sailed when we could and motor-sailed when it dropped below 10 knots, just doing whatever it took to keep moving ~6 knots. This morning, around 20 nautical miles offshore, we spotted land (Mt. Edgecumbe, a dormant stratovolcano) for the first time. It was dark and distant beneath a heavy, grey sky, barely touched by the light of the rising sun.
Ten miles later, we could smell it. Trees. Earth. Mulch? Something that wasn’t ocean (or our own stench 😭 seriously, no one warns you how BAD things smell after three weeks at sea lol). Humpback whales, otters, seals, bald eagles, and ravens greeted us as we entered Sitka Sound. We felt like we were in a National Geographic special. We dropped the sails and motored into our slip at Eliason Harbor around 8 AM local time.
We spent the morning walking around town, picking up bear spray, and grabbing a local beer. Porter got a long, well-deserved walk. Everyone we’ve met has been kind and welcoming. Now we’re back on the boat, salty, stinky, and exhausted, slowly piecing together what comes next. First up is definitely a nap. Then, a shower and laundry. After, we’ll deep clean and start fixing the things that broke along the way. But for now, we’re just sitting still and reflecting. We crossed the Pacific. And it feels pretty damn good 🤍"

What Started as a Dream has Become Something Much Larger
There’s also a more personal layer to their journey now. After Christy’s father passed away, the voyage took on a deeper meaning. He worked his entire life and never really had the opportunity to travel. They now carry his ashes with them as they sail. Wherever they go, they show him the world and allow the world to meet him in the only way it can, in the wind. What started as a dream has become something much larger.
Along the way, they’ve learned that everything is a lesson. There hasn’t been a moment when they weren’t learning something. You quickly realize that no one is going to save you out there. When something breaks, you have to dig deep and figure it out. Self-sufficiency is everything.
Would they do it again? Yes, in every lifetime!





