The adventure of sailing! I first started the dream of sailing when I was in college. I had no money and spent hours studying at my desk in hopes of getting a good job and changing that. I shared a house, kitchen, bathroom, and living room with a bunch of other students and minimum wage people. I suppose that dreaming about sailing was my escape from reality. This was when the first catamarans, the early Prout models, were just starting to make an appearance. I splurged, ordered their literature, and carried it around with me to look at instead of studying. It seemed like these pictures were sometimes the only thing that kept me going.

A friend of a friend, in a campus fraternity house, organized sailing trips to the Bahamas once a year, leaving from Miami, Florida, and cruising the Bahamas for a week over Spring Break. I went on one of those trips, and I was hooked. Eventually, that person was going to graduate and nobody wanted to take his place organizing the trips. He offered to give me all the details, and I jumped at the chance.

These trips were about as low budget as you could get. For a couple of months prior to Spring Break I would plaster all the surrounding colleges with my homemade posters advertising the trip. I put money down to reserve a "sailing yacht" from a place named Otts Yachts. These were more like floating containers lined with double stacked bunks, than a real sailing ship. I could fit 16 people on some of these boats. I would organize all the rides from Ohio to Florida, hire a captain, buy all the food and drinks, and charge people just enough that I could go for free and earn a small amount. A unique blend of chaos and paradise!

One of the captains I hired, married a girl from one of our trips. I kept in touch with them. He worked in a boat yard, built his own boat, and they went sailing south to Panama. I joined this trip for a leg from the USVI to Guadalupe, and all the small islands in between – Saint Martin, Saba, St. Kitts and Nevis, Montserrat, Antigua and Barbuda, and eventually Guadalupe. We had no navigation instruments. We planned our route with paper charts, a compass, and dead reckoning. One morning we woke up and the fog was so thick we couldn’t see 100 yds in any direction. The fog never lifted all day long. We were plenty worried because, by then, with no instruments, we didn’t know if our island destination was still in front of us, or we had passed it and the next land mass was Africa. But, not to worry, my friend had been learning how to tell position with a sextant. He somehow managed to get a noon sun shot and went below to calculate our position. Every so often he would come up on deck because of getting seasick below. Finally, he came up and announced that his calculations put us in exactly the one place we couldn’t be – in the middle of the island of Guadalupe! As it grew dark we thought we heard a bell in the distance and, as we crested a wave, we thought there was a faint twinkle of light in that direction. So we decided to sail that way. At last, we saw more lights, and later that night managed to drop anchor in the bay at the small town of Deshaies, Guadalupe. Unlike this photo of Deshaies I found, we had the harbor to ourselves, and we were one of three boats anchored there.

Since then I have organized, and been on, many sailing trips with family and friends. If you can get a group together that really want this experience, then it becomes affordable as a family vacation. A week in French Polynesia – Tahiti, Bora-Bora, Huahani, Taha’a, and Raiatea. A week in the Mediterranean on a friends boat – from the crusader castles of Malta, to the narrow cobbled streets of Mallorca. As we ghosted over the waves at night, with nothing but dark blue waves horizon to horizon, we smelled and felt the hot arid dust blowing from the Sahara desert and Morocco. Belize during lobster season, where we caught our limit, and numerous trips to the Bahamas, that boasts some of the best snorkeling I have found. My brother-in-law, Doug, enjoys sailing also, so the core group became his family, my family, and other friends we could talk into going to fill the boat. As I experienced all these trips, the end goal was becoming more and more fixed, of sometime, somehow, getting a boat and living that lifestyle. It didn’t need to be a big fancy boat, because I am used to the backpacking lifestyle. Somehow, over the years, this started morphing into a supreme Round-the-World (RTW) adventure.

I am lucky, because my youngest son, Mateo, who will graduate high school in a year as I write this, has also become enamored of the RTW adventure. When my motivation starts to slack, because it has been a truly daunting task, his enthusiasm picks me back up.

In 2017 we bought a $10,000 boat as a fixer-upper. Mateo was only 9 years old, but enthusistic about the work to be done. It was a British built, 30’ Iroquois MKII which has a loyal cult following. It was small and rough, marginally capable of a RTW, and we could afford it. It was in Florida, and I was in Ohio. Another person, who was strongly considering buying an Iroquois, wanted to sail one to see if it could work for him. He worked fishing boats in Alaska during the fishing season. So, we worked out a win-win deal. He would bring the boat from Florida, up the Tennessee-Tombigbee Waterway to Kentucky Lake to see if he liked it, and now the boat would only be a six-hour drive for me. My son and I could start fixing the boat up. We worked on it for a few years. We rebuilt floors, electrical power, cushions, kitchen, bathroom, tillers, mast steps, windows, etc. During this time, little by little, we began to realize that the boat was too small and uncomfortable for us to ever have friends join us on the trip and enjoy it. It was difficult to admit that this boat, that we had worked so hard on, and had been the focus of so many of our world sailing dreams, was not the best decision for us. On the Iroquois, we would be doing the trip just to prove we could, and that was not a good enough reason.

Mateo and the Iroquois tillers that need rebuilt

Iroquois motor mount board that needs replacing

Putting up the mast steps on the Iroquois

Replacing the front windows on the Iroquois

So, now we are at today. The Iroquois is sold. The new/used PDQ 36 Classic is ours, and this is the boat we want. The “SV Cheshire Cat” is born. What's in a name? Of course, it is a "cat"amaran. We both like the eccentric and magical movie “Alice in Wonderland”. In the movie, the Cheshire Cat is the guide to Wonderland, and this boat will be our guide to Wonderland. “- Mad Hatter: Have I gone mad? - Alice: I'm afraid so. You're entirely bonkers. But I'll tell you a secret. All the best people are.”

At this time the trip is a year away and we are doing fix-ups. As they say: being a sailing yacht owner translates as: “working on your boat in exotic locations”. And Kentucky is not even close to an exotic location! But, a year from now, we will be casting off lines and starting the adventure.