Preface

I had a boat before I had a bike.

That’s what I tell folks when they ask how long I’ve been boating.  It’s not literally true, of course; but it’s close.

I’ve owned six boats as an adult: three sailboats that I sailed with my wife Cathy on Long Island Sound, and three power boats on the Chesapeake.

This is a story about the last of those boats – Freedom – and how I single-handedly navigated the entire East Coast with my dog, Guinness.

A New Course

Just before Christmas in 2019, I lost Cathy to cancer, after 51 years of marriage.  Her death really floored me. I lost all interest in my consulting business, and even in my home, which we had loved.

But I knew she wouldn’t want me to sit around home and stare at my navel, and I felt that I just had to try and keep moving forward. So I made two decisions that changed the trajectory of my life. 

First, I found a new companion, a Labradoodle puppy that I bought from a local breeder.  I named him Guinness, for reasons I’ll explain later.

Second, I bought a new boat.

As the winter of 2019 turned to the spring of 2020, we found ourselves in the early days of the Covid lockdown.   I was talking to a friend about a boat I had always admired – the Legacy 32: a Downeast-style express cruiser powered by a 425-hp Cummins Diesel.   

My friend asked, “Dude, you’re 75 years old.  If that’s what you’ve always wanted, what are you waiting for?”

At the time, there were 4 used Legacy 32’s on the market, all in New England.  That weekend, Guinness and I drove to Massachusetts and bought a boat named Freedom.

I figured there was no sense rushing home, since the boat was berthed in Marion MA, right at the top of Buzzards Bay, just south of Cape Cod, with a clear shot to Martha’s Vineyard, Nantucket, and Cuttyhunk.   

Guinness and I spent a month enjoying the islands and bringing Freedom south; we berthed her in Rock Hall, on the Eastern Shore of the Chesapeake.

Back in the Chesapeake, I enjoyed a couple of week-long trips around the Bay, but I immediately began to plan for a trip south on the ICW.  I doubt there’s a boater alive who hasn’t dreamed about that trip.  I had; but calendar constraints (work and family) always got in the way.  And to be honest, I’d never had a boat that was up to the task.  

But now I had Freedom…and the freedom to enjoy her. As I set out, I began a series of blog posts. They were intended to be an online journal: part travelog and part reflection. As it turned out, the daily posts were a good way to stay in touch with friends and family: the posts allowed them to share the journey, and assured them that were safe.

The first part of this book is the story of our first summer on the boat in 2020, recreated from my logs. Then, beginning in October, the book is an assemblage of our blog posts on our trip to Key West.

Let’s get started!