When I read the bio’s of fellow boaters, I always feel like I don’t measure up. I didn’t grow up sailing with my family on the Great Lakes. I wasn’t working on a shrimp boat out of Little River at 16. Getting a chance to paddle a canoe was a big deal because my father HATED boats and refused to even discuss them. I grew up land locked in Raleigh, NC and other than going tubing once with a friend in high school, I never had any real boating experience until I became an adult.
My darling wife, by comparison, grew up on the water. Scituate, MA is a coastal community near Boston on Cape Cod, a truly salty part of the world.

Her father had boats all her life and routinely was on the water. That’s where the happy part ends. She called her father’s boat “The Hell Machine” because she hated going out on it. He was an avid fisherman, and like many young girls, fish flopping around on deck bleeding and snapping was more trauma than wholesome fun.
Somehow we ended up together and had our honeymoon on a sailboat in the BVIs. It was a captained trip on a 50′ sailboat but Dan had a chance to helm the boat close hauled in 20+ knots of breeze and he was hooked. Sailing and the BVIs has been a part of our lives every since.

The BVIs were our vacation spot for years, starting with a monohull sailboat and a second tier charter broker and eventually working out way up to catamarans and more exotic destinations like Grenada, St Vincent and the Genadies, with some Bahamas and Key West thrown in for variety.



Every 2-3 years we’d take some sort of trip. Just us. Us and friends. Us and family. But we managed to keep it up, and steadily upgrade from 40′ monohulls, to 45′ catamarans, to 50′ cats, to 55′ cats, always learning and doing a little bit more. I never felt salty, but I can say that for our week in Key West, every boat in the charter fleet ran aground. Except for one…. the one that caught on fire. AND our boat that we brought out and in with nary a scratch, so maybe I’m slightly more salty than I give myself credit for, at least compared to credit card captains.
After 20+ years of random boating, I was being asked to go run boats for other people on their vacations and even do a boat delivery or two. Nothing paid or commercial, just helping out friends here of there to fill in the gaps between expensive vacations.

It was on one of these deliveries that our future boating plans solidified. I’d always said that unless you used something 12 times per year, it was cheaper to rent. Living in Raleigh, running a company, raising three kids, we certainly were not going to do a lot of coastal boating. Not between volleyball practice, the football game this Friday, cheerleader practice, exams, friends, boyfriends, girlfriends, and a farm, work, and a house to maintain. But my friend Scott, pictured above, decided to purchase a sailboat. He was trying to find a commercial captain to bring it from Connecticut to Oriental, NC when I mentioned that I’d be happy to go get it for him. A comment turned into a plan, which turned into action and next thing I knew we were heading North in a U-Haul to Connecticut with a new dingy and a smattering or boaty stuff rolling around in the back.
We managed to get a ticket in New York, cementing my feeling that a Southern boy has no business in that state. Fortunately we got out of the ticket when the cop inexplicably ran into the back of us before departing. He avoided a Sargent and we avoided a ticket and we hurried out of New York as fast as we could swearing never to return.
Once in Connecticut, we saw the sailboat that would be our home for the next several weeks, and Scotts for the next several years. It had the requisite things wrong with it that a 80s’ era boat would have, but it saw us safely to Norfolk, VA after SEVERAL stops to work on it. It was Norfolk where I turned into a pumpkin and had to finally go back to reality.
But it was after a few of these stops with Scott that I called my Yankee wife and admitted a few things I’d learned.
- Water Yankees are not like regular Yankees. They are friendly and fun to be around.
- Some of these places we were stopping in….. Actually nearly all of these places we were stopping were worth coming back to. They were really pretty and there was a ton to see and do. I felt bad we were skipping so much in our 6 knot rush to get South.
On one of my phone calls to my Mrs, I admitted that maybe the great white North wasn’t as bad as I’d believed, and “I’d like to come back here some day with you, on a boat.”
She said the words that changed our future, “We’d need to own a boat if we did that. I’d be down for that.”
I was still on the Chesapeake, watching sea life stream past when I started looking on Yacht World. Its not my fault. Cell phones still work a couple of miles off shore.
I started looking, like everyone does, at 50 year old boats that we could make into a boat future for us. Prices, post COVID, were still stupid. But maybe if I found the right boat, at the right price, I could convince the Mrs to follow through on her comment and we could become boat owners.
I also, during our hours of sailing/motoring began making a list of wants and needs I’d like in our boat. This is the raw list, straight from Apple notes. Looking back several years later, I’m actually impressed with how many of the things we managed to get in our boat.
Raw list of wants and needs on a boat for us
With a wife who mistakenly said “Lets get a boat” it was time to start looking at boats. I of course had a new sailboat owner in the cockpit with me who was recommending sites and brands for me to look at. But I’d grown up with one name as the pinnacle of boating. Hatteras yachts were the ultimate in boating, and were spoken of in reverence. “Can you believe Sam couldn’t get a raise? His boss has that new Hatteras and he can’t pay him $5.00 per hour!” It was with a start that I realized I’d become old somewhere along the way and those massively expensive Hatteras yachts were now old and affordable.
Thus began the process of looking at old Hatteras yachts, something that I think everyone does at some point. Yacht World looking turned into in person looking to break up the monotony of looking online incessantly. Boats that looked good online, and in my mind, looked scary and rough in person. I wasn’t salty enough to take on a rebuild project and spending 6 months, and a ton of money in the boat yard just didn’t seem like it would work for us.
I also needed to figure out what type of boat we were going to buy. A sailboat? (Quick no, I’m tired of pulling lines) A powerboat? A power cat? Outboard? Inboard? Diesel? Gas? So many choices and the Mrs couldn’t care less. She only knew that “No, I hate that boat.” Or “That boat is nice.” I never knew which one was which and I spent several years presenting boats to her where I was nearly always wrong when I’d try to guess her reaction.
After years of looking at boats, looking at charts, and trying to glean feedback from the Mrs, I finally asked her to take me to Trawlerfest in Baltimore, MD. It was my birthday, and all I wanted for my birthday was a trip to Trawlerfest. On the 6 hour ride to Baltimore, the future Admiral admonished me over and over again that “We are not buying a boat! I’m taking you to this because you asked for it, but NO BOATS are following us home.”
Chartered monohulls. Then catamarans. Dustin’s poem? Bigger cats. Grenada. Captain for others. Pickup of sailboat in CT and desire to come back to New England. “We’ll need to own a boat to sail New England to ‘save money’
Start attending boat shows. Shows in Annapolis. Florida.