Sailing Boston Harbor with — and without — my father
SEPTEMBER 11, 2024
Nothing used to terrify me more than being on those waters. Now, I’m out there every chance I get. I only wish I could tell my dad.
More than five decades ago, a young humpback whale that had wandered into Boston Harbor delighted boaters and onlookers from shore. But my only memory of the juvenile cetacean is my dad urging me from the cockpit of Jalda, our 16-foot plastic tub of a sailboat, to come up and have a look. Back then, though, I rarely strayed from the fiberglass seat at the tiny cabin table, and instead of clambering up to get a glimpse of the whale, I stayed below, my hand glued to the wooden handle my dad had screwed into the bulkhead for me.
Everything about the harbor petrified me: the stiff wind that pushed Jalda into a precipitous heel; the wakes from passing power boats that made her pitch and roll uncontrollably; the gargantuan tankers rumbling angrily past; the jets screaming overhead as they careened toward Logan; and the horrifying night my dad ran us aground off Lovells Island and fired off flares in vain as his young family shivered in fear. Everything was big and loud and frightening, and, as far as I was concerned, that whale was no different.
Lately, a baby humpback has been splashing around the harbor, but now I’m one of the eager boaters craning my neck to get a better look — from the cockpit of a 37-foot sailboat I skipper every day I can. I didn’t just conquer my fear of sailing; I became a fanatic. I’ve sailed across the Atlantic twice and up and down the East Coast several times. But Boston Harbor is my favorite place on the planet. The things that used to scare me stiff — the winds, the waves, the passing ships — are now part of the fun of taking guests out. I regale them with our mishaps of yore, drawing on my dad’s meticulously detailed and delightfully self-effacing logbook (the Coast Guard couldn’t see those flares we fired off that night off Lovells Island because it happened to be July Fourth!).
And I smile at those jets roaring overhead. I imagine passengers from far-off lands getting their first glimpse of my harbor, which is also the last glimpse my father, Al Filipov, got as his plane lifted into the sky on Sept. 11, 2001. I used to despise Boston Harbor and kinda resent my dad for subjecting me to it. Now I can’t get enough, and I can’t thank him enough. It’d sure be nice to tell him.
David Filipov is a retired Boston Globe editor and reporter. He holds a 50-ton captain’s license, sails in Boston in the summer, and has crewed or skippered boats in the Indian, North Atlantic, and South Atlantic oceans.