Sailing Fika

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Our Boating History: From Small Sails to America's Great Loop

Our family's boating journey has been a series of happy moments and challenges, but it's all led us to where we are today: preparing for America's Great Loop.

Alison at the tiller with Ewan and Gwynnie, posing for a picture taken by Chris on their first boat 1977 Catalina 22.

It all started in 2019 when we got our first sailboat, a Catalina 22. Launching the boat every time we wanted to sail was a hassle, but we learned a lot from those experiences. The following year, we trailered our boat to Saint Ignace, Michigan, where we launched the boat and sailed to Mackinac Island for a week of living on the boat. It was a significant accomplishment for us, and we enjoyed exploring Mackinac Island.

Pulling our second sailboat, a 1980 Catalina 22, on the trailer in St. Ignace, Michigan.

In 2021, we upgraded to a 1983 Catalina 30 Tall Rig. We sailed from Holland, Michigan, to Grand Haven, Michigan, where we met a couple on their Loop adventure. The idea of doing the Loop ourselves was starting to take hold. Then, Chris made a significant career change, leaving full-time landscape design to start his own photography business, allowing him and Alison to work from anywhere.

Chris is at the helm, with Gwynnie and Ewan, on our 1983 Catalina 30 Tall Rig.

In 2022, we took a four-week trip from Holland, Michigan, to Frankfurt, Michigan, and then back to Holland. It was a fantastic experience, and we met many other sailors who became our friends. That adventure gave us more insights into what our Great Loop adventure might look like. We also confirmed that our boat could handle the trip but was a little small for full-time life aboard. So we started watching for a bigger boat to fit our family better.

Our trip in the Catalina 30 during the summer of 2022 gave us nearly 350 nautical miles of cruising experience while we lived onboard for several weeks.

And then, Chris found it: a 3-cabin sailboat with many of the features we wanted. Another family of four had been living and cruising on it, which gave us confidence that it was the right choice. Alison didn't hesitate to tell Chris to call the broker, and now we're preparing to launch next week from Virginia in our new boat.

Our new floating home, a 2005 Beneteau 423, is in Deltaville, Virginia.

Our sailing journey so far has been a learning experience, but it's also taught us to be brave and follow our dreams. We can't wait to start our Loop adventure and see where it takes us!