“Something bout a boat, sitting on the sea, out there in the wind, floating… · The Log

“Something bout a boat, sitting on the sea, out there in the wind, floating on the free” -Jimmy Buffett

Gypsy was a good boat. She never let us down, and did everything we asked of her without missing a beat with over 5,000nm under her keel together. But she was never “the right” boat.

Sure, for myself and the two dogs she had ample space. But as soon as I wanted to bring a guest, quarters got tight. Her racer pedigree meant she was frankly, too light and her hull too thin for proper cruising comfort. For being 40 years old she was in excellent shape, but she was not a vessel that I loved the look of. Maybe I’m spoiled after my time with Naida and Grace, but I firmly believe life is too short to not own a boat you love to look at. If you can’t help but turn your head and look back every time you motor away on your dinghy, she’s not the right boat.

After our winter in the Bahamas, back to Chicago we went leaving Gypsy behind with her new owner. Hopefully the right owner. After a few months not even thinking about boats, I got the bug and started searching again. I was determined to make my next vessel a “forever boat” but that came with a few requirements.

Striking Lines. My next boat needs to have the lines and curves that make it a beautiful yacht. From stem to stern, regardless of the condition I find her in, her lines need to be breathtaking. I was spoiled with Naida, she turned heads in any port or harbor we entered. I’m not embarrassed to admit I miss that.
Size. 34’ is just too small for a full time cruiser with two dogs and a large rolodex of friends. I need a boat that I can handle solo with ease, but has the space and amenities to be a wonderful host to guests. My thought was 38’-45’, while I’ve single handed everything from 22’-80’, I don’t see a reason to go bigger than 45’.
Rig. For some reason I got it in my head that my next boat would be a ketch or a yawl. For no reason other than I think they can be beautiful examples of classic yacht design. Also having more sail plan options when solo sailing is always good, right?
Draft. Gypsy was light, but being a centerboard boat with a 4’ draft made her an excellent Bahamas boat. We never had to worry about shallow passes, unlike some of our friends with 7 or 8’. So the next boat needs 6’ or less
Quality/Pedigree. Gypsy was an Irwin 34. Ted Irwin was a respectable builder, he was certainly innovative. He did everything in house, from the hulls, the spars, wood work, even the printing of marketing brochures. Ted was an early adopter of “vertical integration”. But in all the sailor laden watering holes I ever practiced my 4oz rum curls in, no one is ever impressed at an Irwin. Again, I was spoiled with Naida (1935 Grebe custom build) and Grace (7th Hatteras Hull ever produced). I wanted something unique, something special. Call it vanity, I don’t care. The song “You’re So Vain” was in fact, written about me.

So for months I trolled and trolled the shipyards of the internet. Searching near and far for a sailboat that checked all those boxes. A younger me, less mature (lol just play along) and less patient would have waived some of the above requirements in order to get back on the water sooner. But I like to think that as I put more years and more nautical miles behind me, some of that urgency has been tamped down. There were some contenders, but nothing that stopped me in my tracks. I searched a preset of parameters on YachtWorld daily, each day my net pulled in the same catch. None of which stirred me. I set my desktop background to a picture of a Hinckley yawl I found online. I guess I somewhat believe in “manifesting”, I decided I would manifest a beautiful boat like that Hinckley into my life.

One day in late September, as I sat down at my desk with my morning coffee, I started my day as I always did, with a trip to YachtWorld. Only this time, when I pulled my net in, there was gold. It wasn’t there yesterday, but there it is this morning. A boat that checks every box on my list (and then some); it was a listing for a 1975 Hinckley Sou’wester 50.

She’s 50ft, 36,600 lbs, yawl rig, 5.75’ draft with a centerboard that makes her 10’ deep, and lines that would turn even a jet skier’s head. Her sail plan makes her an easy single-hander, and pedigree doesn’t get much better than a hand built Hinckley, designed by Bill Tripp.

After a quick call with the broker that morning, I bought a plane ticket to New York, rented a car, and made the drive from LaGuardia to Sag Harbor out near the end of Long Island. Upon pulling into the yard, there she was. In a sad and somewhat neglected state.

The seller was the original owner, he ordered it from the Hinckley Co. and it was completed in 1975. Per the yard, she had been on the hard for at least 5 years, prior to that she was launched and not used for at least another 5. For 10 years she has been waiting for someone to love her again and bring her back to that sterling Hinckley level of care.

As I climbed aboard to perform a survey I chuckled to myself “am I really doing this again?”

Well, yes. I am.

A little back and forth with the broker, and we came to very agreeable terms. Challenge now has her second owner, and a second lease on life.

She will be spending the winter in Sag Harbor shrink wrapped, come May I’ll launch her and bring her back home to Chicago via the Erie Canal, then we begin what will likely be a multi year refit to create the ultimate cruising Hinckley Sou’wester.

The next chapter begins….