A few years ago, a couple friends were talking about the Great Loop, an adventure that about 300 boats complete every year. Turns out, the eastern part of North America is actually an island and you can drive a boat around the whole thing! Most boats take about a year to complete, but some have done it in less than a month while others are still in progress after 10+ years. It is very much a personal journey for each adventurer. Most people travel with a partner but plenty of others travel solo. I am certainly not the first solo woman Looper but there will be several “firsts” for me – first time captaining a boat other than a pontoon boat in Midwest lakes, first time taking a year-long trip with just my pup (plus some occasional visitors), first time navigating using charts, first time away from my kids for long periods of time, and first time troubleshooting maintenance issues (unless I’m incredibly lucky!).
My first step was attending Captain Chris’ boating school in Vero Beach, Florida in March of 2025. Chris and Alysse Caldwell are Looper vets and now run a boating school out of their home to pass on the knowledge they’ve gained. Such a great experience! 2 days of boat basics and navigation, 2 days of engine anatomy and basic maintenance, and a comprehensive boatyard tour to get a taste of the vast differences between boats. The Caldwells have been such great resources, answering every novice question I had, and sending me links to boats that might be a good fit for me. I learned so, so much but as the saying goes…”the more you know, the more you realize how much you don’t know”.
My most important takeaway though is the truly special Looper community and the kindred spirit amongst Looper vets, current Loopers, and Looper wannabes. I’m still in touch with my Captain Chris classmates and we are cheering each other on from afar. I am hoping we cross paths on the Loop!
After a kickstart with Captain Chris, I joined the American Great Looper Cruisers Association and started reaching out to others. I regularly attend their Virtual Docktails and sit in on topics ranging from “boating with a dog” to “engine maintenance” (hosted by Chris and Alyse!). I have been to several happy hours with Loopers local to Cincinnati and they have been so generous with their information and tours of their boats. I have emailed random solo women Loopers and they have graciously entertained my many questions and provided valuable advice. I have talked with insurance agents, boat agents, and finance representatives. I boat shopped virtually nearly every day to narrow down the boats that will fit me best – diesel, single engine, capable of locking and docking solo, within my price range, highest odds of low maintenance issues, and as small as possible while still allowing the space that I need for Kali plus a guest now and then.
My next step was the Fall Rendezvous in Orange Beach, Alabama in November of 2025. Time to stop dreaming and start doing!
“For the ocean is big and my boat is small. Find the courage.” – Alanis Morissette
To support the adventure or to track The ‘Nati Nomad’s progress, visit greatloop.thenatinomad.com.
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