Just like anything, you start out small and progress as your skills, confidence and budget 
continues to build. I actually began sailing in the 70’s with my brother on Hinckley Lake (Ohio) on small laser style boats, which eventually progressed to 16 foot Hobie catamarans on Lake Erie. Which is where Tom and I met in 1982. He had a 16 foot Prindle. And so it began. Below is the chronology of the boats we loved and learned from. Each one with her own huge personality.
Our early sailing years were spent on 16 foot Hobie and Prindle catamarans that were exhilarating to sail, and “fly a hull”. Our local sailing club was a very active, friendly fraternity on the Rocky River shores of Lake Erie. Occasionally, we also ventured to compete in regional regattas, such as the one pictured here.
Tom’s father was enthusiastic of our love of the water, but was apprehensive of small catamarans and tossed out the idea that we may want to give a motorboat a try. Perhaps he was looking for a more comfortable ride when receiving our weekend boating invitations! For a couple seasons, we had a great time with this Owens 30 foot motorboat, but our hearts were with sailing and eventually, it was time to get back to the wind. In the meantime, we also moved from Ohio to Indiana for work in the late 80’s. And we were introduced to Lake Michigan.
We bought an O’Day 26 sloop and sailed her on Lake Michigan, our new cruising waters. She had lovely lines, a modified full keel, plenty of sail and tiller to steer her by. She, and Lake Michigan, taught us a great deal, including heavy-weather sailing tactics. She also gave us the itch to wander further afar.
Having decided to take the big leap as sailing liveaboards, we needed a capable ocean passage maker, and found it in this stout Alajuela 38′ cutter rig. She was a robust double-ender, heavy-displacement with a full keel. Between 1991-95, she was our home and magic carpet; from Rhode Island to Venezuela and nearly every island in between. Read more on that here: Living Aboard A Sailboat
During our liveaboard years in the Caribbean, we were offered Captain positions at The Moorings Charter Boat Company in the British Virgin Islands. We had previously rented sailboats almost annually in the BVI’s, so we were already very familiar with these favorite islands. For 9 months, we were employed by their crewed yacht division, hosting weekly (and longer) charters aboard a 50 foot Morgan sailboat. It was a lot of work, and an absolute blast!
Our four-year sailing sabbatical came to an end in 1995. After all, we were too young to retire and actually still loved our careers. We were ready to get back to work for a while, grateful to have ‘scratched the itch’ until we could return to cruising yet again once retired someday. But, one shouldn’t throw out the baby with the bathwater! Even though we were working full time, and my elderly mother was nearby, we still needed some ‘boat time’ to carry us through. We bought a Gulfstar 60 that we kept in St. Simons Island, Georgia, and spent long weekends and vacation time aboard.
We sold her in 2016 and had hopes of finding a new boat during the 2016-17 Winter. But then two Category 5 hurricanes spoiled the inventory we had hoped to shop.
Now we’re retired and the song of the sea continues to beckon us. We continue to explore the world by sea aboard Holland America Line ships. See Travelogues/Cruising for complete stories on our extensive journeys aboard.
Life in Nautical Miles 