Whiskey and Ry

In the Alaskan wilderness, Alvah Simon introduces his nephew to the sailing life. From "The Roger Henry File" for September 30, 2008

November 6, 2008


I believe that cruising under sail has the power to transform lives. That alone elevates it to sacred, but when you combine that with the crucible of the mighty Alaskan wilderness it should stir any heart still beating.

Having said that, Diana and I seldom share this life with friends or family, many of whom have over the years asked if they could come on “vacation” with us. That word sends up red flags, for it suggests that they think ours is a life of sipping gin and tonics on the aft deck at sundown. We did that– once.

Missing from that picture are the countless days of boatyard drudgery, breakdowns, bureaucracies, suffocating heat, numbing cold, vindictive gales, and soul-testing calms. Not to mention volcanic eruptions. I always politely refuse.


But the youngest son of my youngest brother crafted his request perfectly when he wrote to say, “Uncle Alvah, I want to learn to sail.” Unfortunately, Diana and I are childless, and we both acknowledge that this has left a hole in our lives. Ryland Jon Simon from Missoula Montana woke something in me. I suddenly felt compelled to pass on whatever little knowledge and skill I have acquired over the past three decades of messing about with boats. I wrote back that he should plan to join us for the difficult Dutch Harbor to Seward leg of our journey.

I found myself a little over anxious, like a father rushing out to buy a baseball mitt for his newborn son. I thought, “I won’t start him with GPS, radar, and C-Map. No, he must first learn to take a bearing, plot and advance a line of position…”

My brother knows me too well and was perhaps worried by my seemingly reckless nature. He wrote to say, “Bring my son home alive and you will never have to buy a drink in my presence for as long as you shall live.” Imagine the investment I (and the good citizens of Lynchburg, Tennessee) now have in this young man’s welfare. Still, adventure by nature does not come in timely, prepackaged amounts, and I will have to risk my windfall to give Ryland an authentic one.


For his first day in Dutch Harbor I arranged for him to go out as a deck hand on a commercial halibut boat. The fisherman are as tough as the work they do, and I wanted Ry to have a glimpse into, as Peter Matthiesson titled his book about fishermen, Men’s Lives. In one day he couldn’t actually learn much about fishing itself but he did learn three words in a new language: mal de mer.

The Sea is often harsh and always indifferent. The moment a person becomes part of the crew, constant contribution and compromise are required. This is a hard adjustment for one who has so often been told you can “Have it your way.” You don’t always get to sleep when tired or eat when hungry. You move to the rhythms of the ship, and you stand your watch, no matter what.

As we’ve moved slowly up the lonely Alaskan Peninsula, Ry has seen that rhythm and cruising routine: weigh anchor, set sail, reef sail, unreef sail, drop anchor, launch dingy, ship dingy, weigh anchor. I don’t know if he is finding this interesting or repetitive.


The progress of many days is measured in meager miles. Is this enough for a 19-year-old used to highway speeds? Does the archaic nautical nomenclature seem unnecessarily complex and pedantic? Does the definition of windward and leeward matter? Will understanding how the center of effort balances with the center of lateral resistance ever prove even remotely relevant in his modern life?

It will take the coming weeks if not years before I can answer these questions, but I hope in the meantime the might and majesty of this land will make its own impression on him. We have seen the rare Stellar sea lions, sea otters rafted so thick you couldn’t count them, eagles flocking like sparrows, rivers where you literally tripped on the fish while crossing, and of course the famous bad-boy bears. Oh, those glorious golden brutes that make every hike an adventure.

We have sailed rough and cold waters in the dark of night, motored through calms, and found protection for the good ship and crew in a dozen lonely anchorages.


I find that in trying to show this life to Ry, I am seeing it anew myself. In spite of the previously mentioned hazards and hurdles, I still more than like what I see.

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