Why is leaving so hard? We have asked this question countless times over the years, and the blog archives are probably littered with posts about departure angst. We like traveling, we don’t mind island hopping, or even making long passages, but for some reason picking a time for departure and actually untying the lines is very stressful. It could be that every time we try to leave, something goes wrong.

Once, one of our kids swallowed a sprite-can pop-top right before a Bahamas trip, delaying us for a few days while we waited to see if we were going to have to spend some time at Miami Children’s Hospital (we didn’t). Another time, we anchored out ahead of a Thanksgiving buddy-boat trip with Jay’s folks and we lost half a battery bank, and a generator breaker switch got turned off accidentally and the remaining batteries weren’t charging. After Rachel was born, we tried to leave the dock ahead of a tropical storm and missed the window to head south, so we pulled into a mangrove-lined bay we knew of and weathered five days of 30-40 knot winds before we could actually leave. One year, we left for the Bahamas, got out the inlet and the water was so rough that we decided to turn around and wait another week at anchor until we felt up to trying again.

And here we are, tied to the dock in Ft. Pierce, with other places and other people beckoning, and we just can’t seem to untie the boat. We’ve had at least three farewell dinners and someone sent us a good-bye key lime pie. At the beginning of last week, we had all but decided to hop over the Gulf Stream when we checked the kids’ passports and realized that four of them had expired in April. Oops! Guess we won’t be traveling internationally for 4-6 weeks!

Some people make it seem so effortless—they circle a date on the calendar, fuel and provision the boat, rise before the sun and untie the lines, sailing away without fanfare or failure. For us, all the stars must be exactly aligned: no sick kids, no storms, no emergencies with Jay’s work, no unfinished boat projects, and no extended-family crises. We want wind from the right direction, calm seas, and a traveling moon. I guess it’s a miracle we ever leave the dock at all.

But then it happens: one morning, after months of discussion and planning, after we’ve all but given up trying to leave, we wake up, feel the freshening breeze, have our coffee while we take a look at the charts, grab a few last-minute items at the store, and start the engines. Without a soul to wave to, we pull in our power cord and dock lines and motor slowly away. Somehow we know when the right moment comes, but rarely do we know beforehand. If you ask me when we are leaving, or where we are going, I respond, “Who knows?” I am not merely being mysterious—I really have no idea. There is a Plan, but it isn’t ours and we’re not informed until we’re well on our way. This kind of spontaneity makes scheduling a bit tricky, but it keeps us humble and provides us with many pleasant surprises.