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Life Lessons from the Spanking the Monkey Tour

2009 July 13
Seven or eight summers ago, a bunch of guys from a town north of Boston clamored aboard a sailboat for a weekend of fun, having no clue that their shenanigans would morph into the annual Spank the Monkey Tour.

It was clear from the start that the trip was a boys' getaway, the hold stocked with beer, rum and home-cooked food. It was also understood that Philip Kersten, the skipper, wanted to include a night sail, which is how we ended up picking Provincetown as our destination instead of somewhere closer like Gloucester or Scituate.

The sail was a straight shot from Nahant, across Massachusetts Bay, to the extreme tip of Cape Cod. We could do it in about 10 hours, leaving late on Friday afternoon once everybody was out of work, and arriving in the wee hours of the morning.

As fate would have it, we snared a lobster buoy en route, not three miles out of Nahant Harbor. It was wrapped tight around the spade rudder and nobody wanted to cut it, but in the end I had no choice, being the only one on board with a knife. We brought the buoy aboard, drew on a monkey face and christened it our mascot.

Before sundown we tied the buoy to a 50-foot line and dragged it behind the boat. For no apparent reason, we thought it a great idea that each of us should individually swim to the monkey and hang on as the boat sliced through the water, then give it a slap before hauling ourselves to the stern ladder. This, oddly, became our initiation rite.

The monkey soon joined our cockpit beer-and-bullshit discussions when at anchor. It was occasionally lashed to the mast and even given a pirate bandana.

Pete Barba, another regular on the tour, was part of the inaugural crew who didn't know a thing about sailing on that first P-town excursion. As he recalled, the wind was building forcefully and the skipper kept telling the newbies how he'd reef the sails if only his seasoned sailing buddies were aboard.

Lessons about lifelines, jacklines, tacking, jibing, and the difference between the high and low side of the boat when heeled at 45 degrees were all part of the shared experience, pieces of the bond. We also collectively breathed the salty air, gazed at the stars, felt the sea rhythmically moving beneath us for hours on end, and relished the subtle sense of adventure that all sailing trips bring, whether an afternoon romp up the coast or a month-long cruise in the tropics. We all silently understood that it's the getting away from the drudgery of daily responsibility and the getting in touch with nature and ourselves that makes such outings so important.

Over the years the lessons presented during the tour became more complex as the green crew turned into sailors. Those of us with more experience taught the craft to those willing to learn-and not everyone stayed with the program.

But for those who did, there has been plenty of adrenaline rush-whale sightings too close for comfort, encounters with sharks while swimming behind the boat, gale winds, boisterous seas, and a singular lightning storm that made us all stand and take notice when a bolt struck the water like a stick of dynamite, sending up a geyser of flames not 20 yards off our bow.

When the water is on fire, you know it's not your average day.

That reckoning marked the end for a couple of the guys, but others were quick to take their places. Since then, more boats have joined the tour, a real flotilla, spawning water balloon wars while under way, and rafting parties in P-town Harbor that threaten to put us on the Homeland Security watch list.

Now those of you who have been to P-town know that it's, well, not exactly a bastion of heterosexuality. Men hold hands and kiss in broad daylight, and the streets are lined with shops selling all sorts of sex toys-whips and spiked collars, chain-mail suits, leather hoods, and devices that frankly still confuse me.

That first year to P-town we were six, a Noah's Ark number that might be misinterpreted as three pairs as we strolled the waterfront. We received plenty of sultry stares and come-ons until one of our crew, Dave the Electrician, held up his hands as we wandered and emphatically declared, "I'm not gay."

It was hilarious if only because wherever we glanced the innuendoes of gay life were present. A few of the locals insultingly called us breeders, but we didn't take offense. The Dark n' Stormies we'd consumed on the boat made us ambassadors of good will. When we stopped for something to eat, it was at Burger Queen, of course, and we even attended live theater with a horde of other sailors, where the musical menu was all show tunes.

Our discomfort shrank over time so that we confidently browsed the shops, not really looking to buy anything, but hoping to be lightly entertained.That's how we came across Spank the Monkey, a novelty store and head shop on Commercial Street with a funky exterior sign that we adopted as our trip logo. Inside, the shelves were laden with bongs and hookahs, scarves, beads, bangles, feather boas and blow-up dolls. Nearby, a sex boutique called Toys of Eros and a lesbian erotica shop named Wild Hearts offered diversion and cause for amusement, especially when a hetero couple came in to ask where they might replenish the rare batteries that powered a gift they'd purchased the previous year. Suddenly, the whole store went silent as we awaited the answer from the manager who was perched on a stepladder adjusting a scantly clad mannequin suspended from the ceiling.

So yes, we're sailing to P-town again this summer, up to five boats, knowing that it will be fun and undoubtedly supply us with another round of stories. It's certainly an unusual trip given the destination, but it's ours, and we've all begun to wonder: Is this how the Figawi began?