Casting Off

Now that you own the boat and you have done the “Four Ps” (planned, packed, plotted and provisioned), the only thing left is to cast off your lines and sail away — right?

For adventure seekers, it is the “hold my beer” part of the adventure. For people who have dreamt of this trip for years, this moment is laced with much excitement. But for us, it was a strange new reality that we were really doing this!

No matter where you fall into these descriptions, trust me, there is no textbook that tells you what is about to happen. Sure, there are webinars, podcasts, social media posts and special interest groups, but the reality is, the Loop is a choose-your-own-adventure that only you can write!

I’ve heard it said recently during a Looper event in Florida: “The Loop is MORE — more challenging, more rewarding, the highs are higher, and the lows are lower.” And while it’s easy to focus on hearing stories of other’s challenges, I am here to tell you that the rewards and experiences you are about to uncover will change your life forever, as they did for our family.

The grace of 30 days

As a busy family of four, the idea of leaving behind life as we knew it was daunting, including selling our home, our cars and lots of other “stuff!” We also had to wrap our heads around the idea of not saying “goodbye;” the whole world seems to think you are dropping off a cliff when the reality is you are a FaceTime or a flight away from maintaining relationships. The other thing we look back on and laugh at is that no matter if you plan to accomplish this epic adventure in a year or three (or even longer), it will truly be gone in a flash, so savor each moment!

My wife says it best by advising Loopers to give the trip the “grace of 30 days.” What does this mean you might ask? As studies show, it takes 28 days to break a habit or cycle — sometimes more and sometimes less. In full transparency, for us, it was a bit of a rough start getting going with mechanical issues, adapting to life on the water and inhabiting a much smaller space than we were accustomed to. I have said to many, “The only reason we didn’t quit, was because we both didn’t want it the same day!”

With that being said, it was an incredible time of exploration: Exploring a new adventure, a new family dynamic and the strength of our relationship. Many say that if your current relationship is in a spot that needs some repair, life aboard may not be the option to fix it; however, for us, I was lucky to have a wife who is a partner in everything that we do — the good, the bad and the boating!

Not just the miles traveled

Looking back, those first 30 days were the foundation for everything that followed. We found our rhythm, adjusted our expectations and leaned into the adventure ahead. The beauty of the Loop isn’t just in the stunning anchorages, the historic towns, or the people you meet along the way, it’s in the way it transforms you.

Somewhere along the waterway, you stop worrying so much about the “what-ifs” and start embracing the “what’s next.” The small victories, like nailing a tricky docking maneuver or watching the sunset from a quiet cove, become just as rewarding as reaching a new milestone. The frustrations fade, replaced by an overwhelming gratitude that you took this leap.

Trust me when I say this: When you cross your wake and the journey eventually ends, you realize that the Loop was never just about the miles traveled. It was about the confidence gained, the memories made and the lifelong friendships forged along the way.

So, if you’re standing at the dock, lines in hand, wondering what’s ahead, know this: The hardest part is leaving. The rest? That’s the adventure — one you’ll never regret and one that, if you let it, will shape you in ways you never imagined.