There’s something magical about going cruising the first time. There’s so much loaded into that journey, so many nay-sayers and personal doubts. So many boats sitting on the dock, while owners spend weekend after weekend getting “ready to go” but never actually leaving the dock with the lines kept aboard.

When you head off (and I don’t care if it’s for a week, a month, a year, or “forever”), you’ve joined a special club.

How do you make a decision to go cruising anyway? The decision we made to go the second time, to take the kids and a year and head south, was made, at least on the surface, over the course of one very memorable dinner out.

Sometimes all it takes is a shift in how you ask a question to open it all up.

It was December 28, 2008, our 15th wedding anniversary. For once we got a babysitter to hang with the kids. We opted for eating outside, next to a loud propane heater thing on the patio covered with a plastic-looking canvas tent with plastic-looking “windows” designed to look, from the outside, like some floppy house. It was not the most auspicious beginning to dinner – we’d been counting on being indoors next to the Tulikivi fireplace on this cold December night, complete with freezing rain and a chilly breeze. But reservations are not normally a part of our vocabulary, so when offered the choice of waiting for 2 hours to sit inside or sitting outside, we shrugged back into our coats and went for the outside.

Drinks ordered, we settled back into conversation. When we did get to eat somewhere without the kids, the conversation was usually about the boat or about sailing. Our first wedding anniversary was spent on Bimini, after a really really awful Gulf Stream crossing, and the tradition of talking about “where do you see us in xxx years” and “what was the best part of the last xxx years” started even then.

“Best part, hands down, was going cruising.” That had been the standard answer since 1997.

“Why was it so good?” I asked. I had my own reasons, of course, and I’d heard Jeremy’s a few times before, but I love seeing him light up when he talks about sailing.

“Freedom. Being in charge of my own choices. Spearfishing. Sailing. Geez, I wish we could go cruising again.”

“Yeah, but that’s not happening again any time soon,” I responded. “We’ve got too much to do here.”

“You’re right.” Jeremy paused. “Let’s put an air conditioner on the boat. It’ll make it more comfortable for weekends aboard. This Chesapeake weather is rough for sleeping when it’s summer.”

We talked about the kind of air conditioner to get, how expensive it would be, what other projects we wanted to do.

I took a sip of wine, then blurted out. “Wait. Why NOT go cruising again? We’ve always talked about wanting to take the kids . . .”

“Why not? Umm, school.” He looked at me like I had 2 heads.

“Homeschool. I'm a teacher, remember?”

“House.”

“We’ll rent it.”

“The boat needs a new engine.”

“Really? Does it?” I was getting into the argument of it. Tell me not to do something, and generally I get fired up about doing it. Contrary nature, I suppose.

“Hmm. Maybe not. And the economy stinks. You’ve already quit your job. I’ll just quit mine.” Jeremy was starting to warm up to this whole idea.

And the conversation continued, getting more and more animated as every objection we could mount became an exercise in figuring out ways around it. We’d stopped asking why we should go – instead we were asking why NOT. It was a challenge. A defiance.

Three little letters.

By the end of that dinner, which had begun in an almost mournful way on an outdoor patio with zero ambience that somehow seemed fitting for a discussion about how everything was better once upon a time, we were casting off our lines in the fall.

Yes, leaving the first time is unbelievable. It shows fortitude and adventure. Showcases a mentality of independence and a little bit of “I don’t really care what you think.” It’s a great dismissive gesture at a society that can’t understand anything different at all. It’s a time of unreal learning, abject fear and terror, and indescribable beauty.

Leaving the second time somehow feels even more momentous. Somehow it means, to me, that we’ve really proved we can do it. Not just once. Bring on the next time.