Taking Wing: Senior Airline Pilot Moments

It is a beautiful starlit night deep in the Bahamas’ Exuma Cays, warm and soft in the light caress of the easterly trades. I am sitting on a white-sand beach moodily lit by the flicker of a driftwood bonfire, sipping a dram of aged rum, and taking an occasional pull on an aromatic cigar. Piper is dozing at my feet, and along with Dawn and my brother-in-law Paul, a number of new and old cruising friends are softly chatting around the fire. All are adventurous kindred souls who have sailed here on their own boats.

I look out over the popular anchorage and can pick out Windbird among the constellation of anchor lights; our floating home glows just a little warmer than the rest. This is a sublime night, and it reminds me of all the other really good days and nights we’ve had in our nearly five years of living and cruising aboard Windbird. Moments like this feel serendipitous, like gifts from the universe we just happened to catch. We are indeed lucky beyond measure—but it is worth remembering that these moments are also the result of conscious decisions, trade-offs, hard work and sacrifice.

For our first three years aboard Windbird, I was a Boeing 757/767 first officer at my airline. This wasn’t an accident; I bid the airplane specifically because it dovetailed so well with our cruising plans (never mind that I had lusted after Boeing’s lithe, sexy 757 since I was 10 years old).

When Dawn and I decided to sell everything, buy a boat and head to the Caribbean, I was flying the McDonnell-Douglas MD-88. This is an airplane with a certain dubious reputation among airline pilots—well-deserved in my experience—but I would have happily continued to fly it if doing so had fit our plans. There was certainly the allure of instant seniority as other first officers bid to bigger, better-paying, less-cantankerous airplanes. But the “Mad Dog” was a year-round workhorse at my airline, with no quiescent season, and its very “juniority”—the fact that people kept leaving it for greener pastures—made it perpetually short-staffed. It was no place for a lazybones pilot looking to hang out on his boat in the Caribbean half the year.

The 757/767 category, on the other hand, appeared to be tailor-made for the pilot who also loves altitudes of 0 feet msl and speeds of 6 knots. It was a niche fleet, with the airplanes mostly paid for and therefore no great need to fly for their keep. The 757 could haul full loads of people and cargo over routes where the 737-900 and A321 struggled; the 767 was big enough to cross the pond with ease but small enough to cover the secondary European routes.

In my adopted base of Atlanta, the fleet flew a ton in the summer and early fall, and it was all hands on deck. I didn’t mind—summer was my moneymaking season, when Dawn, Piper and I made our northward migration while the warm tropical waters spun up fierce hurricanes I wanted absolutely nothing to do with.

During the winter and spring, on the other hand—when there are no hurricanes, when fragrant tropical climes beckon as the sweet, sweet alternative to yet another crappy nor’easter—the 757/767 fleet’s block hours plummeted some 20 percent, and the company refrained from furloughing layabout first officers only because the union contract and training costs forbade it. If some shaggy, wild-brained FO who somehow slipped through the hiring process wanted to voluntarily remove himself from the payroll and sail his dinghy off to the ol’ Caribe—well, have at it buddy, see you in June!

So off to the 757/767 I went. Loved it, loved the airplane—both of ‘em (loved the 757, loved the 767 even more). I loved the destinations; I flew to five continents. Loved the people I flew with. Loved barely even thinking about airplanes as I sailed across the Caribbean, bare-chested and piratically bearded, for weeks and months on end. I even loved enduring brutal shaves and digging my wrinkled, mildew-spotted uniform out of the hanging locker to jet off to the wintry north and saunter into a cockpit I hadn’t seen in eight weeks and put it on like a favorite old sweater on the first blustery day of fall. The real question is: Why the hell did I give that up? It was the best aviation gig I ever had.

Read More from Sam Weigel: Taking Wing

There are a few answers to that, and I think they’re good ones. The first and foremost is that I’m blessed with a wonderfully adventurous, infinitely adaptable wife who has happily tagged along for quite a few harebrained escapades over our 17 years of marriage and sent me off with her blessing for a number more. When I proposed upending our settled life in Minnesota for an itinerant sea-nomad lifestyle, she astonishingly agreed—for a period of one to three years.

Dawn has since turned into a very capable sailor who gladly stands the midnight watch, made Windbird a home, and thanked me time and again for our wonderful adventures afloat—and she has made abundantly clear that after nearly five years on the boat, she is quite ready to return to land. Happily, we found the perfect spot to build our next life together, on a grass airstrip across Puget Sound from my airline’s growing base in Seattle.

Second—and this is a bit difficult to admit because it’s not quite the “cool” attitude in the airline world—I missed being a captain. Mind you, the life of a first officer can be wonderfully relaxing: When some Neanderthal in the back decides that, pandemic be damned, it’s his God-given right to breathe maskless upon the 180 souls sharing his pressurized aluminum tube, it’s quite nice to be able to turn left, share a wry grin of moral support, and say, “Good luck, captain, this one’s all you.” And there is a certain unique professional pride to being a really good FO—the dogged chameleon who adapts seamlessly to his captain’s style, professionally building on his strengths while unobtrusively shoring up his weaknesses. But it’s also really nice to be able to set the tone, run your cockpit as you see fit, buy the drinks on layovers, and do your best to take care of your crew.

Lastly, as I’ve written before, I have a personality that craves change. When things get a bit too static for my liking, I have a tendency to knock down the house of cards and see what I can build next. So, from a fairly early age, both my life and my career have been quite neatly divided into four- to six-year segments. I was a first officer at the regional airlines for four years and in the left seat for six. Five years in the right seat at my current airline was just about perfect, and I was fortunate to have the opportunity to upgrade to 737 captain at that time (and even more fortunate to keep the left seat during the pandemic).

So far I’m glad I made the move, but there have certainly been some trade-offs. I make a good bit more money, the better to sock away for creating our Washington homestead. Naturally, I’m a lot more junior and don’t have nearly the control of my schedule that I had. The 737 is emphatically not the 757/767, but it’s not a bad airplane either, and I’ve grown to rather like certain aspects of it. I don’t get to fly to Europe or South America, but I do regularly tread the West Atlantic Route System to some of my favorite islands in the Caribbean. I’m probably flying more than the piratical, lazybones version of me would prefer—the 737 fleet has been the workhorse of the pandemic. Even in normal times, they’d be working me fairly hard; a junior New York-based 737 captain requesting a winter off to go sail the Caribbean would usually get laughed out of the chief pilot’s office.

Which is why this lovely Bahamas interlude will last but a month. It’s just enough time to revisit our favorite spots in the Exumas and explore a couple of new anchorages, while enjoying some beach bonfires and cruiser potlucks, spearfishing expeditions, and sundowners on friends’ boats—basically a month to reprise the lifestyle we enjoyed so much for three fantastic years. Even getting this time off required the use of 10 days of vacation, front-loading my March schedule and back-loading my April schedule.

That’s OK. A month in these lovely isles is much better than no month. I made such a point of getting back here because it would be just about our last hurrah aboard Windbird. In the second week of April, we would cross back to Miami and sail down to Key Largo to celebrate my 40th birthday with close friends. Then, after flying my April schedule, we would make our last passage north, a Gulf Stream sled ride to Myrtle Beach, South Carolina, where we would complete a long list of boat projects, move all our belongings onto a cargo trailer, and put Windbird up for sale. About the time you read this, we should be embarking on the last leg of our long westward migration, moving onto our nascent grass-airstrip homestead in the hills above Bremerton, Washington. As this issue went into production, I found out that my airline awarded me my requested base transfer to Seattle, effective October, and that I’ll end up fairly senior there. (Astonishingly, I could have even held Seattle 757/767 captain—be still my heart—if I didn’t still have a seat lock on the 737.)

Obviously, it’s a bit bittersweet to be ending this chapter of our lives. But we’re excited for what comes next—not least because we’ll really be getting back into general aviation after occasional dabblings at the periphery for the past five years. We’ve both really missed our Piper Pacer, and owning another airplane is high among our priorities. I feel very fortunate to have a job that not only pays me rather well to do something I love but also affords the flexibility and choices to adapt my work life as needed to enjoy so many of the other neat adventures our fascinating world has to offer.

This story appeared in the August 2021 issue of Flying Magazine