True story: I was a pirate.

I didn’t dress up in some fancy costume: I didn’t throw out “Argh” and “matey!” and other pirate words. I never forced someone to walk the gang plank, nor did I bury any treasure.

I did, however, drink my share of rum: my clothes were ripped, torn, slightly dirty; showers were NOT daily, and I was probably slightly smelly. I wore an eye patch and a sword (it was plastic); and I had a pirate name (which, due to its nature, shall remain unnamed).

I was a pirate. Summer, 1996

I was a pirate. Summer, 1996

It was summer of 1996 and I was 21, taking a summer and semester off of school, escaping from a full college schedule and a job at a local TV station as the morning show producer. I was running, from some vague feeling of restlessness. Within a week of my arrival in Key West, I had managed to talk my way aboard The Topsail Schooner Wolf, a 74-foot, top sail, gaff-rigged schooner that ran tourists out for sunset sails off the shore of the keys. I was one of five of an all-woman crew aboard the ship, and we spent our evenings ushering tourists into the green, sea-foam waters becalmed by the oppressive windless summers that mark the summer months in the keys. We’d motor around for two hours, encouraging our guests to raise the sails and serving them cheap beer and wine. On the weekends, we’d dress up in rag-tag costumes sourced from the local Goodwill store, and we’d spin tales of knife-wielding passengers (true story), violent squalls and yearly water and food fights at sea against the US Coast Guard (also a true story).

At the end of my six months there, I’d learned to sail and I learned that adventure lay wherever you put it. I learned that just because it looked and felt like paradise, that didn’t make it so: that the possibility of adventure lay wherever you were willing to put it.

With time, I stopped mentioning the pirate part of my time aboard The Wolf. And with another decade, I’d nearly stopped mentioning my time in Key West at all, unless I was relating my story about getting the Bends (decompression sickness) while diving off the Bahamas to a fellow diver or sharing some insight on Key West. But for me the chapter had closed, and I had moved on with my typical East-Coast lifestyle.

And then, in 2012, the Wolf came back into my life.



Cowboy is all frenetic energy, ideas and stories. He is Thai-Vietnamese-American. Or Thai-Hawaiian. Or Vietnamese-Canadian-American. It’s hard to get a straight answer. He has been married, maybe a few times, has a few kids, loves Virginia Tech and Pho soup. He has run a business, is an expert cameraman and has been homeless. He is, technically, homeless now, save for a small bunk on the Wolf crammed full of him. He believes in angels and luck. His real name is Cao Boi, and no he does not have another last name. He is always talking, thinking, moving to the next thought, and talking. And he is gladly at the beck and call of Captain Finbar and the rest of the crew as cook, mate, galley wench, hop-to, instigator and mediator, and pirate on the Wolf. I know all of this in our five-minute walk to the local 7-Eleven where we are getting ice.

We troll back to the dock, lugging a cart of ice behind us together. Cowboy woke up 20 minutes ago: I woke up two hours ago and I cannot match his energy. I am merely trying to capture a bit of it. I imagine a lot of us around Cowboy are doing the same.  “So, Laura, tell me about yourself,” Cowboy says. “What’s your story?”

I have to think about that one, pause in its telling. “Well. I was married. Technically I still am, I guess.” In Maryland, you have to be separated for a year before you can even file the paperwork for a divorce. “It was a rough marriage, and even rougher separation. But it is getting better,” I tell him. I am only slightly uncomfortable with the telling: This is the first time I’ve really been able to succinctly sum up my current life, the first time I have told a stranger my story. It feels surreal, but it makes it final and real.

“I sailed on the Wolf for six months when I ran away to Key West from school and work. You know, for a break. I found the Wolf the first day I was in Key West and I said, ‘I want to learn to sail, and I want to sail on her,’” I tell him.

“Yes, The Wolf will do that,” Cowboy says. He squints at me from the side of his eyes. “I have been on and off the Wolf for six years. I have owned a camera shop, and done many things. I’ve been married — and divorced — too, and I have a son. But I always end up back with her. My family doesn’t understand it.”

But I do. I haven’t been on The Wolf since I visited Key West in 1997. But I still have dreams about sailing her.  For the past 15 years I have woken up in the middle of the night with glimmers of a dream where I was handling The Wolf’s lines again, making fast the jib sheet after a tack, battling epic forces of nature amid howling wind. There’s not a single boat I sail that doesn’t take me straight back to the decks of the Wolf. I have no other sea stories than those I gathered while I sailed her, but I don’t need more: She gave me plenty in those six months. “She is in my soul, Cowboy, and that was after a short time. I can’t imagine what happens if you’ve sailed on her for even longer.”

The Wolf  drifted on the Chesapeake that day

We sail her that day from Baltimore to Annapolis, where we exchange the “Conch Republic ” flag with the “Maritime Republic of Eastport” in a ceremony full of the nature of two pieces of the US that have jokingly seceded from their homelands — Key West from the United States, and Eastport from Annapolis. I spend three days with the Wolf and her crew, Captain Finbar and his pirate wife Julie, and at the end of it return back to my single family home in the burbs of Baltimore, while the crew journeys on their coastal tour of the US.

Later, after I see her and her crew off the docks of Annapolis, I am talking to my friend Karen. She knew I sailed on a “pirate ship” in Key West, saw the photo of the Wolf hanging on the wall in my office. She’d heard the stories, knew my journey there and back. But she hadn’t seen me on The Wolf, hadn’t realized the depth of her reach into my being. “The Wolf came in and saved you when you lived in Key West,” she says. “And she’s come back to save you again.” Until she said it so succinctly, I hadn’t realized that’s exactly what my time aboard her was doing this time, too.


We love pirates: something about the romanticism of the freedom that comes from being a pirate, the imagined carefree attitude to do what you want, when you want, beckons our internal sense of adventure. The rag-a-tag nature of pirates, the devil-may-care approach to life seems to answer the internal siren call of living life for life’s sake. It calls to us in the midst of how we really live it — get up, fight traffic, go to work, go home, do some errands, take care of all the stuff around the house and in our life. The life of a pirate, with few earthly possessions and calling a 6-by-4 foot berth and wherever it may be in port, “home” renews in us the right sense that there is, indeed, a life out there most of us are just not living — at least not the way we want.

Want to know what Happy looks like? Hang with Cao for a little while

Want to know what Happy looks like? Hang with Cao for a little while

In all the studies of what makes people happy – truly happy, fulfilled, experiencing life in a positive manner no matter age or life circumstances — “stuff” does not make the list.  Instead, new indications are that overall balance and harmony with the environment and with the individual’s sense of place in the world creates more happiness than any single indicator of wealth or power. Just ask the Kingdom of Bhutan in the Himilayas, which measure GDH (Gross Domestic Happiness) instead of GDP. New measures social scientists are using point to factors like access to health care, free time with family, natural resource conservation, a sense of giving back and other “soft measures” as being more indicative with overall happiness.  (Want to read more? I recommend, “A New Measure of Well-Being From a Happy Little Kingdom“). The documentary Happy sums it up succinctly: spend an hour and watch it to walk away feeling….. well, Happy.

So  maybe it’s not the swash buckling tales of pirates that have us so enraptured, as much as it is a sense that pirates, surely, must have had free time to explore and do the things that filled their soul.

After The Wolf left that summer in 2012, I embarked on my own land-loving adventure to rediscover what happiness really means — to re-capture those pieces of myself and my lifestyle back in my pirate days that had made me feel so at peace with the world and the ocean. I don’t know if I am there yet. But today I can say that almost every day, I live just a little piece of the Pirate’s Life.