Cigars & Sailboats: I Might not Have Any Actual Hobbies

I used to snowboard around or just under 200 days a year. Something like that. I used to keep track when I lived in a mountain town. When you're keeping score like that — that kind of commitment to anything — it takes care of the guess work. You know what you're doing and why you're there.

Back in the day nosepress, "Yes, chef!". Photo, Dano Pendygrasse

Back in the day nosepress, "Yes, chef!". Photo, Dano Pendygrasse

Eventually Peter Pan grows up and becomes a boring, post coke-binge Robin Williams, only starring in movies about Peter Pan. Now I sit on a computer over 300 days a year, a score I don't want to keep. That doesn't mean I no longer have it as good as the free-wheeling, Manboy years of careless shredding and boozing at Garf's. Things are better, if anything. Far better. I have worked hard for a financial freedom that I can only imagine is some kind of sick joke, ready to be ripped away at any moment, Gotchya, bitch. I live steps off the white sand and blue Caribbean Sea in a place too big for our needs. I am getting married to an amazing woman that you'd have to meet to believe her kindness, compassion and equal love for the bottle, high-fives and fart humour.

There's no replacing what I wake up to now, but what's replaced snowboarding? So far nothing. Surfing is the answer you're thinking of, but we pulled a Kansas City Shuffle and went east when we could have gone west. We chose crystal clear calm water and white sand over grey swells and brown sand. The thing I look forward to at the end of my days is smoking a cigar and having a drink on one of our palm tree covered patios. That can't be my new hobby, can it?

If you don't have a love for the sea, I'm not sure you've ever spent any time on it

I've wanted to sail for a long, long time. To steal from an older post, if we've been drinking together and I haven't mentioned diving off the bow of a boat, we haven't been drinking enough. Almost everyone has this dream of owning a boat and sailing on the open sea or coastal reefs off some remote island. We're halfway there, but without the boat or skill set. Lately, we've been taking out small catamarans, lying to the rental company that we know how to sail. Day one, no idea what we were doing or how to steer the damned thing, but determined to hit the water we just said, "What kind of gringos do you take us for? Of course we know how to sail!"

Two hours after being off the coast, we were getting the hang of it. Kind of. We could get the boat where we wanted to go, but getting it back to shore presented a problem with the wind and our lack of any ability whatsoever. We were rescued a hundred metres from shore. Fuck. I thought we had this. We now go out whenever we can on the little boat and can launch and land it no problem. We still suck, I just know it.


When you've been good at your previous pastime for most of your life, it's discouraging and exciting at the same time to be a beginner at the next thing. It's like being terrible at surfing. It's unexplainably exciting even though you spend half the day drowning. We'll get there, but it's going to take some time, some money and a lot of lost dignity.

Any activity that involves the ocean will ultimately teach you this important lesson: Pride stays on the beach in a lawn chair.

Until someone moves down here into one of our spare rooms and teaches me to sail, I'm going to be stuck with no real hobbies other than working, smoking, drinking and getting lost at sea.