Once the surveys were complete and we made the decision to move forward, we felt like we had a fairly solid understanding of what we were stepping into. The reports confirmed that the Endeavour 44’ TrawlerCat was fundamentally sound, and we thought we had a clear picture of the items that needed attention. Looking back now, we realize we were about to learn an important lesson about how plans on paper don’t always tell the full story of life on the water.

Overall, she was in good shape, but like any older vessel, there were a few maintenance items that needed to be addressed before we could safely make the trip north. One of the bigger ones was the cutlass bearings, which had to be replaced. There were also several smaller issues that came out of the survey—nothing unusual, but all important to take care of before putting her through a long passage to the Chesapeake.

So while excitement was building, we were also working through a growing checklist of repairs. Coordinating haul-outs, scheduling yard work, and making sure everything was properly completed became our focus. Each item checked off felt like one step closer to bringing her home.

From the very beginning, we always knew we would hire a professional captain to deliver the boat to her new home port. We were honest with ourselves about that—this was not a passage we were ready to take on alone. It was the safest and smartest choice, especially given the distance and complexity of the trip.

That said, we had also hoped Joe would be able to join Sandi for the delivery, not only to be part of the experience, but to start learning the boat hands-on during the journey. Unfortunately, timing had other plans. Joe was still working full-time and couldn’t step away from his job for the trip north. That meant Sandi would be making the delivery voyage without him.

And then there was the small detail we may have glossed over in all of this…

We didn’t actually know how to operate the boat ourselves yet.

It’s one thing to research, plan, and prepare—but quite another to realize that Sandi would be onboard for the delivery while Joe stayed behind, both of us still very much in the learning phase of this new life. It became clear that this trip wouldn’t just be about moving the boat—it would be an important learning experience, even if we weren’t both there to share it together.

Because bringing her home wasn’t just about hiring the right captain or checking off a repair list.

It was about stepping into a completely new chapter—and learning as we went.