Operation: Flee

looking down from the top of a sailing boat mast at a crew member on dock, looking back up


Fabio and I spent countless hours developing infinite routes to tackle on the imaginary boat that we didn’t own. Our motto for this activity was “No Wrong Brainstorming”, a philosophy borrowed from Liz Lemon/Tina Fey on 30 Rock.

The first trip we planned was along the coast between Panama and Venezuela, in a dugout Kuna canoe with a sail. From there, our sights jumped to a 40ft sailing yacht that we could charge through the treacherous Drake passage around the southern tip of South America, through the fjords in Chile, to the magical island of Chiloé.

When we began to focus on smaller, older boats that we could actually afford, our route planning became more realistic as well. Not to say that a small boat can’t go far…one dream route for us at this time was to travel up the east coast of North America and skip across Greenland and Iceland to Ireland.

Ultimately, the course we set was based on two realities: seasons and finances. Our extended refit period meant we were just splashing the boat on Halloween, when all reasonable boat owners on the south coast of Massachusetts were hauling their vessels out and shrink-wrapping them for the winter. We needed to get south to warmer climes, and also to a place where we could refill the coffers.

Like so many snowbirds before us, we charted our migration to Florida. We would need to hustle as far south as Norfolk, VA to dodge the falling temperatures and winter squalls of the Northeast, and then tuck into the Intracoastal Waterway to pass the gauntlet of Cape Hatteras. From there, we could take it easy and poke around coastal towns in the Carolinas, Georgia and Florida. The destination would be southern Florida, where superyachts overwinter, and seasonal crew jobs are plentiful.

As they say, a journey of a thousand miles begins with a single step, and so it was with SY Tranquility. Our first step was the baby one from New Bedford to Fairhaven Shipyard across the bay, where we would stay for two more weeks shaking down the boat for problems. That 5-minute crossing was the most nerve-wracking moment of the whole project up to that point. Would the fiberglass repairs hold? Would the propeller shaft leak? Would the electric engine be powerful enough? Is our rigging balanced? Are we good enough sailors?

We hovered over the bilge with a flashlight for those first nights, not leaving the boat alone for more than a few hours at a time. We threw a pizza party in town. We hung out with my parents, who came to visit. We recruited an experienced sailor to join our crew (more about that soon).

Finally, a favorable wind came and it was time to stop saying goodbye, and actually leave.

looking over the water from a boat
Kate and Fabio embarking, finally, on their journey, leaving the Hurricane Barrier that protects the bay between New Bedford, Massachusetts and Fairhaven on a Sunday in November.