Joy and I have been sailing since 1997 and both of us have undergone formal training. Neither of us, however, has done anything like what we’re trying to accomplish here.
The Olivia Grace is our third sailboat. Way before marriage, I owned a 1976 Peterson 34, an old IOR race boat that was fast AF, and totally unstable down wind. It was also perpetually sinking. Indeed, it was not uncommon to discover the floorboards floating three miles offshore. The Peterson was sold to help finance our first home, but once we had some breathing room again, we purchased a 1987 C&C 36. The C&C was ugly and slow, but served us well for eight seasons. We sold the C&C right before Evelyn was born in 2007.
In 2014 we decided that the kids were ready to start sailing and we began searching for a family-friendly cruiser. With a distant horizon in mind, we only considered true blue water boats and the Pacific Seacraft sprung towards the top of the list. “Loon,” as she was called at the time, was then offered by Larsen Marine, her previous owner having mothballed her after his Caribbean to Pacific adventure. We closed on the vessel in the spring of 2015 and began getting to know her.
Going was not always smooth. True of any vessel with an elongated keel and skeg-hung rudder, she has a wicked propwalk, which took 3 seasons to fully master. The engine (a Yanmar 3cl.) also had a horrible habit of suddenly losing power when hot and under load. It took 2 seasons and 3 mechanics to finally diagnose and replace a damaged fuel injector. It has been reliable ever since.
Slowly and methodically, we ironed out the wrinkles, learned how to handle her and developed a “friendship.” A sailboat is not an inanimate object—it’s a living thing with a mood and sometimes a will of its own that the crew must come to understand and to appreciate if they are to get along. The act of sailing is a conversation between crew and vessel.
We sailed as much as possible in the build-up to departure. Each year our crossings grew farther from Chicago, to New Buffalo, St. Joseph, South Haven and Saugatuk on the Michigan side, and to Racine, Sheboygan and Washington Island on the Wisconsin side.
“Boat Schooling”
We targeted the winter of 2020/21 as it best fit the kids’ academic calendars. As any Chicago parent will attest, the pressure to get into a good high school is significant at age 13, perhaps more significant than the pressure to get into a good college at age 17. Everything relies upon 7th grade and three entrance exams. By the time we untie the lines in 2020, Evelyn will have taken all three exams and her middle school grades will be “in the can.” Frankie will not have even entered the fray.
Fearing pushback from Queen of Angels, we first contacted the head of Catholic schools at the Archdiocese of Chicago. I was advised, however, that the ultimate decision to support us was solely the province of Queens’ Principal at the time, Julia Kelly. As consolation, I was also told “your kids will learn more on that trip than they will in 6 months of school.” The support, albeit conjectural, was surprising nonetheless.
In September 2017, we requested a “sit down” with Mrs. Kelly. To our surprise, she echoed the sentiments of the archdiocese and was more interested in hearing about our plans than she was in making sure the girls’ “saint studies” were completed on time. Indeed, “everything is on-line and you can email assignments when you get an internet connection,” she said. That was a relief. With the school’s support, we were one step closer to cast off.
Health and Medical
Our first appointment with the Northwestern Travel Clinic occurred in the winter of 2019, a year before our targeted date of departure. Vaccinations were administered and anticipated medications were prescribed. These, along with numerous tubes of surgical glue, round-out our offshore medical kit.
We followed up with the travel clinic in August 2020 regarding Covid-19. Although our case worker would not confirm availability, she suggested a return visit in early December for vaccination. Fingers crossed.
Home
All bills are on auto-pay, house-sitter installed, and we’re ready to depart. We also subscribed to a mail-forwarding service so that we can receive and read mail while away. “Kitty” the dog will be shipped out to Gramma and Papa right after Christmas; she too will be spending her winter in the tropics.
Voyages of Olivia Grace 
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