Follow Diana Phillips, Marshall Miller, and Makenzie (a 10 pound Havanese, also known as Kenzi) as they begin the epic 6,000-mile Great Loop, starting from Chicago in September, 2022. Two of the three are close to octogenarian status. (It’s never too late for a happy adventure!)

I (Diana) grew up boating on the South Holston Lake in the ’50’s on the BobbyDiana, a steel hulled boat built by my father and named after me and my brother. Being on the water is my happy place. In 2000, I bought a 30’ Catalina named “Shibumi Maru”, and sailed out of Burnham Harbor in Chicago. After selling Shibumi, I spent many hours searching the internet for another boat.

Marshall owned a ski boat for a time, but never really thought about boating until he met me in 2021. I introduced him to the possibility of living on the water and he fell in love with the idea. So, on October 1, 2021, we took possession of ESCAPE, a 42’ Ocean Alexander built in 1987. It was one of those “falling in love” experiences. From the first moment we stepped aboard her, we knew she was our boat.

I am realizing a dream to navigate the Great Loop, starting in Chicago and crossing ESCAPE’s wake a year later in Lake Michigan. For Marshall, it’s a brand new chapter, having had only ski boat experience. He is quickly adapting to life on a boat and becoming proficient at helming and docking.

We spent the winter outfitting ESCAPE for her 6,000 mile trip, including adding bow thrusters for easier docking and redoing some of her isinglass, internal hoses and AC systems. An aluminum-hulled Highfield dinghy along with a new Tohatsu 9.9 outboard were added in July.  (Supposed to be added in May, but we, as many others, fell victim to the supply chain delays.)

After spending the summer on Lake Michigan, learning the subtleties of handling Escape, we are targeting September 2022 to begin the trip down the Illinois, Mississippi, Ohio, and Tombigbee rivers, winding up in Mobile Bay. There we will decide whether to cross the open Gulf or hop-skip along Florida’s coastline, to what will be our winter home in St. Petersburg Municipal Marina.

We plan to winter in Florida, do any necessary repairs, and start the second part of the Loop in March 2023, heading across the Okeechobee Waterway and north via the ICW (Intracoastal Waterway) to the St. Lawrence Seaway. Hopefully we will be able to “cross our wake” in just under one year.

The hard part, of course, is leaving behind family and friends for extended periods. We will  secure the boat in Florida and head home for the holidays, because spending Thanksgiving and Christmas away from our families is unimaginable.