About Michael Labadie
I graduated from Goddard College in Plainfield, Vermont in 1974 and moved to New York City to pursue a career in photography. Over time, my work shifted toward real estate development. I began converting lofts and developing buildings both in and outside of the city.
In the early 1980s, my wife Anne and I began sailing. We bareboat chartered Nautor Swan yachts in Sint Maarten, Newport, and Villefranche-sur-Mer, France—usually the Swan 46 designed by German Frers. Back then, before Leonardo Ferragamo bought Nautor, the company ran a clever bareboat program that doubled as a marketing effort to entice people to buy their yachts.
Then, in 1997, everything changed. I was diagnosed with Acute Respiratory Distress Syndrome. What began as pneumonia spiraled into a critical condition where my immune system turned against me and my organs began to fail. I was placed in a medically induced coma, and at one point, my pulmonologist told my wife I had only a 5% chance of survival.
After two months, I came out of the coma completely debilitated—unable to speak, move my limbs, or sit up. I had lost 50 pounds and was completely atrophied. I spent the next four months in a rehab facility relearning how to speak, eat, and walk. Eventually, I returned home.
It’s hard to explain how an experience like that changes your perspective. Everything feels more vivid, more meaningful. Life slows down in the best possible way—you really do stop to smell the roses. I told my wife I wanted out of the rat race. I wanted to sell the real estate portfolio and buy a sailboat to sail to Europe.
In 1999, we chartered a Ted Hood–designed Hinckley 43 in Southwest Harbor, Maine. We were actively searching for a boat to call our own. Although we liked the Swan 46, the bridge deck and traveler setup felt too
dangerous with our two young children aboard. After the charter, I spoke to a Hinckley broker about a Sou’wester 50. It was stored in a barn, and to reach it we had to climb up a ladder to a Tripp H-48, and then cross over several boats. My wife, the kids, and I made the trek, but somewhere along the way, the kids disappeared. We found them inside the Tripp H-48, the first boat we’d climbed onto.
“Look, daddy, this boat is great!” they called out. “This boat would be perfect.”
Within days, we were under contract for the H-48. Originally named Escapade, we asked the kids to choose a new name. They’d been reading Brian Jacques’ Redwall series and loved a squirrel character named Song. The kids suggested that we name the boat after the squirrel.
After a light refit, we commissioned Song in April 2000 and sailed her down the East Coast, stopping along the way to explore American historical sites for the kids’ education. We reached Port Everglades, Florida, where I loaded Song onto a Dockwise Yacht Transport ship bound for Palma de Mallorca.
Our two children, both eight at the time (adopted and born just three months apart), finished the fall term before we pulled them out of school. Anne, who holds a master’s in special education, used the school’s curriculum to homeschool them.
The family joined me in Palma that December. We wintered in Mallorca and, come March, set sail across the Mediterranean. We cruised from the Balearics to Sardinia, Sicily, Tunisia, Lampedusa, Malta, Italy, Greece, and Turkey.
One of my favorite memories occured on the Turkey. I sat on a rock while Anne cut my hair on a quiet beach surrounded by wild thyme and roaming goats. A shepherd appeared, pointed to his own head, and sat down where I had been—clearly asking for a haircut too. Anne obliged.
In 2001, we returned Song to Newport and cruised New England for several years. Then in 2006, I sailed to Sint Maarten via Bermuda and spent the season exploring the Caribbean before returning to Newport. That route became a near-annual tradition.
Since then, I’ve sailed as far north as Nova Scotia and as far south as Cartagena, Colombia, and the coasts of Mexico.