Stowie’s Top 10 Sailing Rules

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The summer solstice kicked off the first day of our dockside programs in Martha’s Vineyard. All the parts of a quintessential New England summer are here–sunshine, a warm breeze, art, music, and a life-sized inflatable sperm whale.

Even David Letterman stopped by to check out the big whaleship that sailed into port. He liked the experience so much, he even went for a row in one of our whaleboats. He looked like a natural!

Lettermen (center) enjoys a row in our whaleboats!

Letterman enjoys our whaleboats!

In honor of Letterman, I’ve compiled a Top Ten List of the peculiar lifestyles I’ve both observed and inevitably discovered in the sailing world. Here they are.


10. Don’t bring umbrellas or whistles on board. It’s bad luck.
9. Don’t question superstitions. That brings worse luck.
8. Cherish hot showers and ice water. They’re rare phenomenons.
7. 70 percent of your clothes are given to you by the sailing company you previously or currently work for. The rest are from Goodwill.
6. Your physical address is not permanent and floats away. You should probably get used to being a vagabond.
5. Don’t go into public with your rig knife. You will be labeled as armed and dangerous.
4. Get all the mileage you can out of a couch cushion before sailing. Comfy seats are rarer than ice water.
3. A good port has showers. A great port has ice cream.
2. Just when you need it most, you can never find that economy pack of Q-Tips.
1. When going aloft, “It’d be silly to let go.” -Irving Johnson “Around the Horn”

Yours truly,

– Ryan, A.K.A. “Stowie”