O Captain! My Captain!

Sailing has long been a mystery to me. I’ve taken Sunfish out at summer camp in Ontario, and once I rented one in Barbados. I’ve shot around Lake Jordan on a Laser. But Sunfish and Lasers are dinghies. That’s a different kind of sailing.

The big sailor in our family is my brother Glen.

Glen lives in Lion’s Head, Ontario, which is a picturesque sailing village on the edge of Georgian Bay. Georgian Bay is frequently cited in the sailing literature as being “up there” with the Mediterranean as one of the great sailing venues on earth.

He owns sailboats. He enters sailing races. He hangs out with sailors. And when it comes to sailing I have always been his tag-a-long little brother. I’ve joined him on many “day sails” on Georgian Bay, and I have been lucky enough to be included in a subset of his bigger sailing adventures.

I jumped in when his buddy Captain Lumpy leased a boat in the British Virgin Islands. We sailed to the Bitter End, and to Virgin Gorda, where the Caribbean meets the Atlantic. We cruised around on a giant mono hulled sailboat. I joined them again when they sailed from Guadalupe to Dominica and back. Also a single hulled boat.

With my modicum of sailing experience, I volunteered to help my friend Eric sail his ketch from Long Island to Maine. That was a hectic trip. Motor sailing the entire way, two masts to worry about, at the helm through Martha’s Vineyard in the dead of the night. Four hours on, four hours sleep, for days.

At my father’s memorial service in Guelph, Ontario, Lumpy came up to me and said, “You know, we are departing Baja into the Sea of Cortez next week. If you hightailed it to North Carolina and caught a plane, you could make it on time.”

I did that. And I went on an amazing “wilderness sail,” (no place to re-provision for days) again on a big old mono hull.

That’s the trip when I sold a bottle of Fair Game wine to the bartender at Hotel California. I smuggled it past customs in order to remedy the basic problem:

So I called up the Captain

“Please bring me my wine”

He said, “We haven’t had that spirit here since 1969.”

Never mind that wine is not a spirit. Suffice it to say that after we departed it was possible to get some wine at Hotel California. Problem solved. It’s one thing to be a wine captain. That I have done. No one questions my ability to sell things.

But sailing is another story. I’d never been captain. I had never leased a boat. Never charted a course. Never planned a sailing trip. Never made the decisions associated with what the boat would do next. The only thing I knew for sure was there is not a more powerful feeling than being at the helm, with full sails, whipping across the water. I had tasted it.

A decade ago I “qualified” as a captain to sail a boat out of Oriental, North Carolina. It was basically a bunch of web forms, and I never followed through to rent the boat. Lost my nerve.

Being a captain was some kind of psychological wall for me. Maybe I was scared. It could be my suspicion that crew hands that rent boats are posers. Lack of confidence is not something I am known for. But there it was. I only sailed with my sailing buddies from Canada.

It could be an “older brother” thing.

The day you match your older brother at anything is a mind-blowing rite of passage. Doesn’t matter if it is arm wrestling, or a game of chess. I think maybe I was afraid to embark on my “Captaincy” because of a desire to remain a tag-a-long to my beloved brother Glen.

Enter the Covid Pandemic. I didn’t go anywhere, or make any new friends for about a year. The more I complied with public health suggestions and orders, the more I died inside.

At one point I succumbed to a horrible sickness. As I oscillated between fever and chills, too sick to read, too sick to watch TV, I played the new family fun game: “What If This is the End?” I lay in a pool of sweat enumerating my regrets. Sailing was one of them.

When my man-cold receded, I began my journey.

I found a catamaran for lease in Ft. Lauderdale. I pinged Sarah, who I knew owned a boat and had done some sailing off the coast of North Carolina. I basically begged her to join me, and I asked her to take a run at qualifying to rent the boat. She was interested. She said her boyfriend Tyler had some sailing experience. She started talking up the trip with her sailing buddies—looking for a captain.

The trip I had envisioned was to sail from Florida, across the Gulfstream to The Bahamas, to deliver Karen, who we all started referring to as “The Package.” She had no sailing experience, but she is from The Bahamas. Our job was to deliver her home.

At this point I should probably issue a "postcard alert." I paint postcards for my grand daughter Margot. We have an active snail mail correspondence. She's four years old. That means she's not quite a critic, yet. Which is a great relief to me. I paint with impunity, and she saves my postcards as if they matter. If you spot a surprisingly amateur painting in these entries, think, "Margot."

When Sarah struck out recruiting local sailors, I took the plunge. I’d never sailed a catamaran. I had zero experience with the Gulfstream. I lined up sailing references. I created my “Sailing Resume.” I took a sledgehammer to the cinder block wall that had been holding me back.

Sarah and Tyler were in.

I tried my hand at recruiting the rest of the crew, offering spots to sailing buddies who were trapped in Canada due to Covid restrictions. I offered spots to customers, and friends in Moncure. When I landed John and Julie, I booked the boat. They had zero sailing experience, but John knows a lot about how things work, and Julie is an avid adventurer.

We gathered as a group a couple of times, to talk about safety, and headings, and protocols. I charted an “S” shaped course that would take us south to Miami, then into the Gulfstream, and dump us out at the Biminis in The Bahamas.

I read books, and watched You Tube videos, and struck up conversations with strangers that had done such a “crossing.” I bought a sailing chart for the Straits of Florida and Bimini. I bought a Cruising Guide to the Bahamas, I bought a book on How to sail Catamarans. Karen bought a copy of Islands in the Stream by Ernest Hemmingway, which was written about the Bimini island chain.

No one can say we didn’t “prep” for this journey. Sarah and Tyler bought flashing LEDs to affix to life jackets. Everyone started watching “crossing videos.” John and Julie started brushing up on their wind apps, we started reading Gulfstream predictions, and we studied the weather window.

I bought an extra night on the boat, at shore, to familiarize us with its systems, and I ran through a checklist of its equipment—learning where everything was stowed—and how to turn stuff on and off.

On February 18th, the occasion of my 59th birthday, we set sail on a 42-foot catamaran called Sybaris.

In 720 BC, Sybaris was an important city in what would become southern Italy. With good soils, and a busy port it became known for its prosperity, hedonism feasts and excesses. Its residents were known as “Sybarites.”

2739 years later, we embarked on an amazing sailing trip throughout south Florida.

Here are my logs from the trip: