Sailing Lesson

A month-long cruise down the Pacific coast from Port Townsend, WA, to Ventura, CA

A year ago, after searching for land to no avail, as well as not finding inspiration, I got interested in sailboats.

If it’s a midlife crisis, it means I’ll be sailing until I’m 130 years old!

I sailed and raced dinghies as a teenager, cruised the Baltic Sea right after high school, and fished commercially in Alaska for five seasons, but otherwise, I hadn’t been at sea for 45 years.

After browsing the classifieds on Boat Trader and Yacht World, I took off for New Orleans to go help my friend Maury get his newly purchased sailboat ready. I spent a week working and sleeping in intense heat, and continued to Florida where I started looking at boats for sale, stopping at every marina and boat yard along the way.

I kept driving up the eastern seaboard all the way to Maine, and then worked my way back down the coast. I looked at dozens of boats, was tempted to buy a few of them, drove 11,000 miles, slept in Walmart parking lots, often starting my days at Starbucks (they open at 5:00am in some places) and finishing at Wholefoods, looking for my next boats to go visit. I am grateful for corporate America for making my trip safe, predictable and digitally comfortable!.

On my way back, upon reaching Jacksonville, Florida, I decided I had enough of looking and wasn’t ready to buy a boat. My deep dive into the world of sailboats was an eye opener as far as what it takes to refit a boat to make it ocean-crossing capable.

So I thought it would be wise to go sailing first, regain my sea legs and assess whether that lifestyle suits me, or if it was just another fantasy.

I signed up on a popular crew-finder website and created my profile. Most people looking to crew on boats are young, pretty, handsome, fit and experienced, so I wondered what chance I would have to get on a boat having next to nil offshore sailing experience. I stated that I used to be a farmer and, as most people know, small old-time farmers have to do everything and are usually pretty resourceful, tough and mechanically savvy.

I got in touch with a couple captains but nothing was happening. Then one day, I get a message from a captain who liked my profile story. Darn, my luck! His boat is an Oyster 56, a luxury yacht.

I had an hour interview with him, and I was in. I flew to Seattle a couple weeks later and got on the boat in Port Townsend where it was anchored. Luxury indeed! Built in 2006, the interior is all oak cabinetry and flooring, the boat has hydraulic furlers for main sail and genoa, electric winches, air-conditioning, freezer, induction electric stove and oven, water maker, and top notch electronics. The owner, being from the Mediterranean, likes fine food and even bakes his own bread! For my first offshore cruising experience, I’m going to be spoiled!

I spent 31 days on the boat, and cruised 1,200 miles, visiting Port Townsend, Neah Bay, Newport, Eureka, Monterey and Ventura, our last stop. Because we spent several days on anchor at each stop, I could describe many technical details about repairing a broken motor mount on the main engine, adjusting valves on both main and generator diesel engines, replacing a circulating pump for the heating/air conditioning system, replacing salt water hoses and exhaust elbow on the generator, redoing the caulking on the front part of the teak deck, and polishing and waxing the deck and cabin. I could talk about all the gourmet breakfasts and dinners I cooked everyday, and giving the boat a complete interior cleanup-bilge, engine room, storage and pantry.

But more importantly, I want to share my experience cruising double-handed (just me and the owner) with a very talented, experienced, demanding and tense captain. Having lived on fishing boats for months on end, with talented and demanding captains, or difficult crews, I had some practice in the matter.

I’m still digesting the experience as I write this, but let me tell you that it may have been one of the most meaningful experience of self-growth, self-mastery and self-control I may have ever had.

Many of you know me as being quite intense and demanding sometimes... Well, this month-long cruise, working my buns off, turned out to be a remarkable exercise of being completely in service to a boat and her captain, practicing not taking anything personally, being incredibly patient, kind, generous and loving. I have to say that it was humbling to be on the receiving end of impatience, snappy communication, and expectations well above the norm, especially for a non-paid situation.

Each day, I cultivated a grace and equanimity that I never though myself capable of mustering. Each day, I meditated on the millions of people who are in situations where they have to shut their mouth if they wish to keep their job. Everyday I said yes, and kept diving deeper into a sort of detachment from my needs. Each day, I found more opportunities to embrace qualities that had thus far eluded me, having a history of often getting triggered, reacting with anger, having high expectations, or being often disappointed. Each day was like re-entering the meditation hall, ready to face my demons, surrendering to the teacher, and having many opportunities to watch my mind and reactions.

I can’t say that I learned a lot about sailing or being on a boat that I did not already know. That will be for my next cruising experience. But I can wholeheartedly say that this was one of the most valuable spiritual experience I’ve ever had. One where I saw in me the seeds of goodness, kindness, generosity, patience and detachment. It gave me hope that I can overcome the effects of childhood trauma that always seem to have me living on edge, or on the fringe. I am very proud of myself, and surprised by the unexpected outcome of this cruise.

I am already looking for my next crew position, and look forward to practicing being impeccable, not just with my attention and concentration, seasoned mechanical and cooking skills, but with my patience and kindness. That way, when/if I buy a boat, I will be better prepared to be a good captain, one who manages to keep his crew happy, safe, educated, and above all, eager to return as crew for the next exotic destination.

However, I am in no rush to buy a boat, or being a captain. I have a lot to learn and am eager to do so. For me, the prospect of growing emotionally during cruises is as exciting as sailing surrounded by whales or dolphins, and for the time being, I am looking for inspiration.

I’m very grateful for having found my sea legs again. I am also very grateful for having been given the opportunity to cruise on a gorgeous boat with a captain who was a good teacher of maritime knowledge-navigation, docking, anchoring, weather, diesel and systems maintenance, rope making, sail repairs and baking bread!