Nearly Thoughtless Thursday: I Could Do It Too

For some time now, my wife Pamela has been following a blog called Zero to Cruising. Started by some visionary folks who, many years ago, were in the same boat we’re in now (figuratively, not literally), it’s one of several blogs and other creative endeavors that fueled her dream to buy and live on a sailboat.

And a few weeks ago, these folks shared a video about some other visionary folks—specifically, a family that has managed to capture, in beautiful world-wide sound and color, the quickening spirit of a life on the water.

Of course, I hate all these people.

But please don’t get me wrong. It’s only because I know I’m yet too small to be like any of them. And that’s one reason I’m genuinely thankful to be aboard Meander this Thanksgiving Day. Room to grow.

That is, if I’m up to it. I guess we’ll see.

Meanwhile, if you have thirteen minutes and forty-three seconds to spare, this glimpse from the deck of a cruising family’s sailboat might give you some insight into why Pam has been thinking about the cruising life all these years.

Newbie Cruisers: The First Three Months of Bimini Dream

When my wife and I first decided five years ago that we would someday go cruising as liveaboards in our own sailboat, we were keenly aware that neither of us knew the first thing about sailing. So we started the pursuit of this dream by throwing ourselves into studying the art.

Book learning. . .

We began with the books, learning from them what we could of the wind and the water, of the behavior of the boats that ride them, and of the vocabulary used to describe that behavior.


“The Complete Sailor” by David Seidman. One of our earliest. Still one of our favorites.

. . . is never enough.

Soon thereafter, we hit the wind and water we had been reading about. And in our first few years of struggling to get our boats to behave the way the books said they would, we began to learn a whole new boat vocabulary, much of it completely inappropriate for a family-rated blog. (Let’s just say we discovered that the salt in “salty language” comes from the sea.)

Of course, we could not expect otherwise. Books are a fine place to start, of course. But in cruising as in life, there’s just no substitute for going through a thing–the old chestnut eventually comes around to reassert itself: “Good judgment comes from experience, and experience comes from bad judgment.” And bad judgment is OK as long as you live to tell about it.


Of course, when possible, it is preferable to learn from the experience of others.

So far we’ve come

So, three months into the life we’ve been dreaming about for the past five years, it seems like a good time to take a look back at Bimini Dream and see what living aboard Meander has taught us so far.

It goes without saying, of course, that we’ve barely scratched the surface. And it’s just as well, at least until I’ve mastered snorkeling.

snorkeling guy

Actually, I’m not sure I can pull this off.

So far to go

If anyone were to ask about a newbie cruiser’s life on the water, I would sum up the first three months as follows.

All the things you will go through—the things that leap out at you from your decks, from the docks, from the marinas and the boatyards, from the supply stores and the chandleries, and from your own books and computers as you try to wrestle the rest to the ground—all these things might well conspire together to push the wonderful reasons you started this broad reach right out of your head.

Don’t panic, and don’t despair. The next time your sails take you out on the water, you’ll remember.


–Book: Mike Webster.
Ship aground on the beach of of Puerto Baquerizo Moreno on San Cristobal Island by John Solaro, shared under a Creative Commons license via photopin.
Above the overworld from underworld by daveynin, shared under another Creative Commons license via photopin.
–Between the bridges: Mike Webster.

Anchors Aweigh: Our First Sail on Meander

This past Monday, I posted three lists of everything we thought we had to do to accomplish three goals: first, launch Meander; then, conduct a shakedown cruise; then, embark on our first major trip.

I say I posted these lists this past Monday. But it would be more accurate to say I wrote the lists the previous Thursday and scheduled them to be posted automatically this past Monday.

This “dissynchronization” is necessary because the small, remote marina in which we found, bought and boarded our new floating home is virtually out of the line of sight of most of the nation’s cellular providers. So every time my wife Pam and I want to check our email or our phone messages—or access our blogs to post our latest insights—we have to leave the marina and drive out to the top of a hill about four miles away to park in the shadow of two communications towers. To work around this obstacle, I have started writing a few posts in advance, and then driving out to that hot spot to upload each with scheduling instructions.

The downside to pre-scheduling one’s posts is that one never knows whether what one has written on Thursday for an appearance the next Monday will be substantially changed by events occurring that Sunday.

But I digress.

SO. . . This past Monday, I posted three lists I had written the previous Thursday of everything we thought we had to do to build up to our first major trip.

But this past Sunday, we tossed the first two lists overboard and went out for our very first sail in Meander.

It turned out that the well-past-overdue task of pumping out our holding tank (more on that here) simply could not wait for me to get all the way through our list of “Preparations for First Launch.” Fortunately, that errand required nothing more than a short trip under motor power to the boatyard next door, and a mercifully uneventful application of the suction hose at the yard’s pump station.

Okay, not completely uneventful. But the tactical error I alone made with the hose while under vacuum pressure resulted only in spattering my own face and clothing with minor amounts of watery ordure. All innocent parties in the vicinity remained unbesmirched.

Once that was over, we were back in the wind and on the water. And the wind and water told us that all the engine stuff we had yet to learn, all the freshwater and sanitary systems, all the batteries and the lights. . . all that could wait. Because although we didn’t yet know enough about Meander’s systems, the one thing we really did know is how to sail her.


I know what I’m doing. I know what I’m doing. I swear I know what I’m doing.

So we motored south out of Cockrell Creek and into Ingram Bay. And while I manned the helm, Pam wrestled with Meander’s sails.

On any sailboat equipped with an auxiliary motor, the helmsman can make the crew’s sail-raising task easier by using the motor to head directly into the wind. This causes the wind to come from directly forward of the boat instead of over either side, which in turn keeps the sails being raised from filling prematurely with air. Because when they are finally and fully raised, the air filling those sails can pull a fifteen-thousand pound sailboat through the water. But when the sails are only partially raised, that same filling will fight any crewmember’s best efforts at getting them completely up.


Does this guy know what he’s doing?

So as I tried to motor into a modest ten-knot wind that was swinging slowly from the northwest to the northeast, Pam went forward to the mast and applied herself to the main halyard. This is the line that raises the mainsail, and the sail went up without a hitch.

Then Pam turned her attention to the headsail. On Meander, we have a roller furler, a clever device that keeps unused headsails stowed in a tight roll around a sailboat’s headstay. The headsail is unfurled for use by pulling on one of the two lines on a sailboat known as jib sheets. (Why are these lines called “sheets?” I have no idea. If you had asked me five years ago to point to a “sheet” on a sailboat, I would have pointed to the mainsail and observed, “That sheet is big enough to cover any ten beds I ever slept in.”)

The wind continued to veer to the northeast, and flowed over Meander’s starboard side (making this the side “to windward”) as I chased its changing direction with the bow of the boat. Assessing these conditions correctly, Pam moved to the port side (the side “to leeward”) and pulled on the jib sheet.

And out the headsail came, down the port side of the boat, filling beautifully (and, thanks to the superior skills of the helmsman, not too violently) with the wind blowing over the starboard side of Meander.

Then, just as Pam tied the jib sheet off on its cleat and I killed the engine, the wind backed again to the northwest. Crossing the bow, it turned the port side of our boat into the windward side.

And the headsail, so beautifully filled out from the port side, flopped into an awkward position toward the boat’s centerline. And the changed wind pushed us off the course it had been encouraging us in just moments earlier.

This condition is called “backfilling the jib.” At ten knots, it’s not particularly dangerous. And for some maneuvers in certain conditions, it’s even useful.

But in “condition-free” conditions on the open water, it’s mostly just a thing in which the wind catches you and reminds you who the boss is. A thing that other, more experienced sailors will point to from the shoreline or from other boats as they laugh and shout, “Just you wait. It gets worse.” A thing to be vaguely embarrassed by, and then to recover from.


If you give me kibble, I won’t tell about the other ten times you messed up.

And recover we did. With a quick change of lines and a course correction, we straightened Meander out nicely enough. Then we put in a few miles of easy, peaceful “getting-to-know-you” sailing, up and down the Great Wicomico River and out to the threshold of the great Chesapeake Bay, before heading back to our slip in our little marina out of the line of sight of most of the nation’s cellular providers.

Back to our slip to apply ourselves to those lists we abandoned just for a day. Because if we’re ever going to step over the threshold and into the Bay, we’re going to need them to get ourselves ready.

Meanwhile, Sunday was a wonderful reminder of why we bought this boat in the first place.


All photos: Pamela Webster

Our home on the water.

A week ago yesterday, I wrote the origin story of an engagingly mad endeavor my wife Pam and I have undertaken. Having left behind all reason as we know it, we have spent the past five years pursuing a lifestyle known as liveaboard cruising and a sailboat on which to live it.

And in that origin story, I alluded to the few signatures, the two documents, and the boatload of cash that had to be pushed around in order to land us last Tuesday on the deck of our new home on the water.

It’s been a busy week since I posted that origin story. And during it, we’ve learned again (had we forgotten before) that pursuing “Admin” can be an endeavor all its own, albeit one whose madness is not nearly so engaging.

So the bad news is that last Tuesday came and went, and we are still one document swap away from closing.

The good news is that the sellers didn’t care.

It seems that during the protracted march we took through the many lenghthy steps leading to this point, our negotiating partners had come to trust us. At least, they trusted us enough to have allowed us to move last Tuesday after all.

So we are now in de facto possession of what, after a final handoff to occur at 2:00 PM DST today with all the ceremony befitting a Wawa convenience store parking lot outside Mechanicsville, Virginia, will officially become our first sailboat. And our fifth home.

Ladies and gentlemen, at the risk of being eight hours premature, I give you Meander.


Our home on the water.


Photo: Mike Webster.

And so it begins.

One day back in 2010 or so, my wife Pamela was in her rather too well air-conditioned office in our hometown of Ithaca, staring with longing through the window at the rare sunshine and relative warmth of an Upstate New York summer.

And she decided then and there that she had had enough of anything and everything that can possibly be conveyed by the word indoors, and she came home that evening and let me in on something that had apparently been on her mind for a long time.

“I want to go cruising.”

“Okay.” Pause. “One question. What, for the purpose of this discussion, is cruising?”

Apparently, not this.

Apparently, not this.

“Cruising is what we’ll be doing when we’ve sold the house and bought a sailboat, and are sailing her to places I would rather not drive or fly to.”

“Oh, okay.” Pause. “Another question. Don’t we have, uh, jobs?”

“Yes, we do. But we’ll leave them. And we’ll start a business we can run from the boat. And until it’s up and running, we can live off the extra proceeds from the house sale.”

“I see.” Pause. “Just one more, for clarity’s sake: Do you know how to sail?”

“No. Do you know how to sail?”


A long pause, during which I contemplated this fact: In our household, the traditional and time-honored role of The Keeper of Good Sense had, until now, been held almost exclusively by my wife.


“Well, then, I guess we had better learn how to sail.”

“So it would seem.”


That conversation was five years ago.

Tomorrow, subject to the successful completion of various maneuvers to collect seven signatures, transmit two documents, and drain our bank account of considerably more than half its value, we are stepping aboard our new home on the water. One that moves. And floats. And will stay floating. Hopefully.

So please stay tuned. This, it would seem, is just the beginning.


photo credit: DSC06880 via photopin (license)