On this, my fourth windjammer trip of the season, I consider myself a bit of an expert at packing.

Of high importance to me is the messenger bag containing a digital camera, minicassette recorder, red wine, and other important tools of the journalist trade.

In my duffle, I pack two pairs of Carhartts, a hoodie, socks, underwear, t-shirts, a wool sweater, winter cap, down parka, and gloves.

My toiletry bag holds toothpaste, a toothbrush, aspirin, deodorant, and the pack of baby wipes I purloined from my son’s nursery. (After a few stagnant days at sea, nothing boosts your confidence quite like a brisk, whole-body rubdown with a few baby wipes. They’ll keep you as powder-fresh and soft as a baby’s bottom — a big plus aboard a ship with a limited supply of hot water.)

Of highest importance, however, is my dry bag. In it I keep a sleeping bag, a foul-weather jacket, and foul-weather pants.

Grace Bailey
Captain:	J.R. Braugh
Owner:	Ray Williamson
Built:	1882
Length:	80'
Capacity:	29 passengers and 4 crew

The Grace Bailey at sail.

Augnice Ayotte

The Grace Bailey was built in Patchogue, New York in 1882. She hauled timber, granite, and perishable goods until 1940 when she began carrying passengers.

Every traveler packs a rain jacket, but few think to buy matching pants. So, before you take a trip on a windjammer, you must do two things: 1) buy a reliable pair of foul-weather pants; 2) pray you don’t need them.

Today, as the Grace Bailey departs Camden Harbor and slips into dense, drizzly fog, it’s clear my prayer has gone unanswered. It’s a mid-June morning—nearly the official start of summer — and yet it’s a wet 58 degrees off the coast of Maine.

This isn’t unusual. The mean average temperature on the first day of summer in Midcoast Maine is 63°F. In many coastal Maine households, the furnace still kicks on during the wee hours of a June morning.

For someone arriving to the Midcoast from Boston or Baltimore (where the corresponding average temperatures are 70°F and 78°F, respectively), 58°F can be an uncomfortable surprise. Add in a full day of drizzly weather, and you could quickly become intractably morose.

But foul-weather gear is a remarkable thing. Like spacesuits or scuba gear, foulies allow you to explore an otherwise inhospitable atmosphere, and you might be surprised by the novelty of it.

Hell, you might even enjoy it.

And so it goes with my experience. I’m dressed head to toe in waterproof fabrics and leaning against the rain-beaded rail on the Grace Bailey’s quarterdeck, but I couldn’t be happier. Sure, it’d be nice to feel the sun’s warmth and spy the gently rolling Camden Hills off our port beam, but there’s something deeply authentic about this experience. The cool, damp air has chased many of the passengers toward the warmth of the galley stove, and, for the most part, the few that remain on deck are crewmembers.

This is how it used to be.

In the days when cargo was king, a coasting schooner like the Grace Bailey would’ve set sail with the barest of crews. The holds, which now house up to 29 passengers, would’ve been filled with timber, and a mere two or three men would’ve raised the sails, weighed the anchor, and driven this lonely vessel from port to distant port.

If an award could be given to historical accuracy, today’s sail is a worthy candidate. Apart from a few brave passengers, the forward deck belongs to the mate, Andy Gardiner (whom you may recognize from the Mercantile’s shakedown cruise earlier this season), and the deckhand, Santiago Taussig-Moore.

This is a rapscallion pair of sea dogs if there ever was. Wide-brimmed sou’wester hats obscure their eyes from view, leaving nothing upon which to base your first impressions but their scruffy, grinning mugs.

Captain J.R. motors the yawlboat.

At first glance, you might assume the vessel was run by furloughed prisoners. Santiago (or Santi, as he’s known) is a tall beanpole of a man. He grew up on 113th Street in Manhattan’s Upper West Side, and he’s as heavily inked as Queequeg. His arms are virtual sleeves of kaleidoscopic tattoos, and his neck bears an illustrated sparrow eternally trapped mid-flight between Santi’s jutting collarbone and his fine jaw line. When you first meet him, it’s no stretch to imagine Santi wandering the late-night streets of Camden hawking ‘balmed heads to morbid tourists. (To be honest, upon first meeting this illustrated man, I was scared shitless.)

Andy, a Tennessean, sports an Ahab beard and a Letterman smile. In fact, Andy seems to be forever grinning. It’s as though he’s in on some universal truth that the rest of us have yet to internalize: A general disregard for politesse makes for an honest, manageable, friend-filled existence. Then again, when your id is as winning as Andy’s, there’s little need to suppress it.

Ray Williamson owns the Grace Bailey, but today it’s driven by Captain James Richard Braugh. Captain J.R. looks a bit out of place amid these seagoing ruffians. Sure, he’s been working for Captain Ray for 16 years and he’s as salty as anyone in the fleet, but he carries a certain amount of old-world refinement. Captain J.R. just earned an M.F.A. in oil painting from the New York Academy of Art, he’s a talented multi-instrumentalist, and he’s simply an all-around nice guy. A few years ago, when Men’s Journal was doing a piece on the best jobs in the country, the editors chose a smiling portrait J.R. for their opening spread.

You’d think that this element of dandiness might be a liability in the schooner bum world, but Captain J.R. pulls it off. He’s easily one of the most well-liked and respected captains in the fleet.

At the moment, Captain J.R. appears a bit distant. He stands at the helm nursing a mug of hot coffee while scanning the fog for signs of the oil tanker that’s rumored to be chugging northward in our vicinity. It’s an understandable distraction.

The Rules of the Road favor our vessel for two reasons: 1) commercial tankers are encouraged to stay within the charted shipping lane in the center of the Bay; 2) ships under sail are given right of way over ships under power. Therefore, if we stay out of the shipping lane, we should remain safe; plus, even if we strayed into the shipping lane, we automatically have the right of way.

However, there’s a colloquial rule that usurps all else: the Rule of Tonnage. In other words, if you’re tooling around in a VW Bug, you probably shouldn’t mess with a Mack truck.

The following epitaph perhaps sums it best:

Here lies the body of Michael O’Day,
Who died maintaining his right of way,
He was right, dead right, as he sailed along,
But he’s just as dead as if he’d been wrong.

Andy Gardiner.

On any other day, Captain J.R. would’ve determined which way the tanker was heading and gone the opposite direction. After all, a destination in windjamming is a rare thing. Often the sole item on a windjammer’s itinerary is to return its passengers to their cars on the scheduled date of return. Aside from that, captains prefer to take their passengers wherever the wind and tides favor. In fact, on the morning of Day 1 most captains make a point of declaring some variation on the following:

“Don’t ask me where we’re going; I have no idea.”

Today, however, we have a set destination: the Schooner Gam in Holbrook Island Harbor.

We’ve all heard the term “pod of whales,” but it might be news to learn that “gam of whales” is synonymous. Gam can also refer to a friendly visit between whalers.

Apart from perhaps Santi, there are no harpooners in the windjammer fleet; nonetheless, gam is an evocative word, so it’s employed to describe the fleet’s yearly tradition of rafting up at a designated meeting point.

Captain J.R. Braugh.

Today—like some variation on It’s a Mad, Mad, Mad, Mad World—nearly all the vessels in the Maine Windjammer Association are plowing northward toward Castine to gam up. (“Gam up” is the verb form, which is essentially synonymous with rafting up. [“Gam up” can also be used to describe an amorous liaison between two schooner bums, but that’s way outside the purview of this particular website.])

As we sail between Nautilus and Holbrook islands, the gam comes into view. It’s an impressive sight. Nine different vessels fly colorful flags under a low ceiling of gray clouds. There are two separate rafts this year; the tight jumbles of hulls, masts, and rigging resemble a small archipelago of thickly forested islands. The Heritage and Angelique have dropped anchors to form a gam in one area; the American Eagle has dropped anchor to form a gam in another. The rest of the fleet has divided and tied up to whichever gam was most convenient during their approach.

After we lower the Grace Bailey’s sails and prepare to gam up alongside the Stephen Taber, Andy offers an unguarded statement.

“No matter how many times I do this, it still makes me nervous.”

If my last trip with Andy hadn’t given me enough reason to like him, this admission clinched it. Too often, schooner bums are preoccupied with their own nonchalance. When you ask them whether clinging to the end of a bowsprit or teetering high atop the mainmast is unnerving, they’ll grin as though the question is absurd.

But Andy’s uncensored divulgence is humanizing; it adds more to his force of character than it could possibly subtract from his salt.

I’m nervous, too—not so much for the process of gamming up as the gam itself. We’re approaching nine other vessels with their attendant crews and passengers. Hundreds of people will be cavorting tonight in this unlikely harbor outside Castine, and I’m experiencing acute social anxiety. As if it isn’t enough to find yourself alone on a ship of strangers, the encroaching possibility of endless small talk can be paralyzing.

As it turns out, neither Andy nor I had anything to worry about. The Grace Bailey alights against the Taber’s fenders with a gentle bump, and the gam is easygoing and festive.

In my travels this season, the question I’m most often asked is, “Which windjammer is the best?” While there’s honestly no single answer that could possibly verge on truth, I will say that the gammed fleet is greater than its parts. Not only can you tour the fleet of ships and experience something akin to a Greatest Hits collection—the storytelling of Captain Doug Lee, the quick wit of Captain Garth Wells, the soulful harmonica of Captain Noah Barnes, and much more! — you’re also privy to a sudden super group of outsized personalities.

The gam.

When we finish our lobster dinner aboard the Grace Bailey, Captain J.R. takes a seat on the starboard rail, tunes his acoustic guitar, and leads the passengers through a sing-a-long of several folk standards. Next, Captain Noah joins him for some impromptu accompaniment on harmonica and guitar. Later, a group of musicians forms on the forward deck of the Lewis R. French: Captain J.R. provides bluesy improvisation over Cara Lauzone’s fiddle, and the Irish banjo playing of a Lewis R. French passenger.

It’s standing-room-only aboard the French, so I watch the spectacle unfold from the slightly less-crowded deck of the neighboring Angelique. The rain has picked up again and the passengers huddle together to watch the show from under the awnings that cover each vessel. As I scan the lantern-lit crowd, I see there isn’t an unsmiling face among them—an impressive feat on an otherwise cold and dreary June night.

Ben McCanna is sailing aboard all of the boats of the Maine Windjammer Association during the summer of 2008 and is chronicling his trip on Down East.com.

Santiago Taussig-Moore.

The views expressed on this Web site are those of the authors alone and do not necessarily represent the views of Down East Enterprise or its employees.