PicoBlog

August 3, 1492: Christopher Columbus, a master sailor/navigator, left Spain on history's most consequential voyage of discovery.

Five hundred years later, August 3, 1992: Richard Gilbert, an amateur yachtsman from Wilmette, Illinois, set a course in Columbus's wake on what turned out to be his voyage of discovery.

Columbus had a fleet of three ships, 90 men, was backed by Queen Isabella of Spain. He'd spent eight years following her and King Ferdinand around Spain pitching his idea, called "La Empresa de los Indios" (the Enterprise of the Indies).

By sailing west, he'd find a better route to the East with all its riches. He was a great sailor and also an entrepreneur. Besides ships and men, he negotiated a 10-percent cut of all he discovered plus a title for himself and his descendants in perpetuity…." Admiral of the Ocean Sea."

My deal wasn't even close. I gave it about two years in the planning. It would be a personal commemoration of the quincentennial of history's greatest sail. I coaxed five middle-aged friends to come sailing with me. We sail the Columbus route as closely as possible to the historical record in his log.

Together we bought a used 45-foot sailing ketch (two masts) and renamed her 'Empresa.' We had no royal backers or need for plunder.

The crew elected me captain, mainly because it was my idea.

We held several training sessions in the Chesapeake Bay, where we bought the boat. We prepared menus and grocery lists, and watch schedules. We all took the Myers-Briggs personality test to learn how best to communicate with one another. Everyone had a job.

My dentist taught me how to repair a broken tooth. He gave me dental tools and dry ingredients to make the cap. We took first aid refresher courses.

One of our crew produced a medical kit rival that of a cruise ship which was not surprising because he was CEO of a cruise line. Another became our sailing master because besides running an outdoor sign company in Chicago, he was a racing sailor on Lake Michigan. Our navigator was head of a consulting firm, a good sailor, and a true nerd when it came to electronics.

GPS was coming in after being proven by guiding smart bombs down chimneys in the first Gulf War. But we took a sextant just in case because the U.S. was still doing what was called 'selective availability' government-speak for "we can turn off the satellites whenever we feel like it." (That happened off the coast of Cuba on our voyage.)

Our morale officer was a long-time public relations officer for the same cruise line. The crew member charged with nursing our boat's 80 hp Mercedes auxiliary diesel engine was an engineer from Pennsylvania who had once taught diesel mechanics at the Army's Aberdeen Proving Grounds.

And me? Just a suburban newspaper publisher/CEO in Chicago's northern and western suburbs. I had done a fair amount of sailing in the Chesapeake Bay, coastal cruising as far north as Maine and Lake Michigan. I learned to sail on Iowa's Lake Rathbun.

We asked and received an Illinois flag from Governor Jim Thompson to claim possession of San Salvador (if we made it) as Illinois property. Why not? Columbus declared every place he landed as Spanish territory.

We arranged for our boat to be delivered to Europe (sailed from Annapolis, MD., to Portugal.) We hired a delivery captain named Wally, and as part of the crew, my daughter Liz, then 21 and a Michigan State junior, came aboard with two others making a crew of four. Her ocean crossing was a tough slog, and she has her own sea stories to tell. There is an extra special father-daughter bond because we've crossed the same ocean, at different times, together.

Out of dozens read, my best resource book was Samuel Elliot Morrison's "Admiral of the Ocean Sea: Life of Christopher Columbus." It won the Pulitzer Prize for biography in 1942. It is still available in paperback on Amazon.

Columbus had set sail from Palos de la Frontera, Spain, a village on the river Rio Tinto six miles up from the ocean. Five centuries later, we were in place on August 3, 1992, to hoist our anchor at Palos. With the morning ebb tide pushing us, we headed for the Canary Islands. In the 15th century and now, these islands are a Spanish possession about 100 miles off the northwest coast of Africa. For Columbus, it was a jumping-off place for his voyage west into the unknown.

There were other boats in the harbor on August 3, 1992, and we were anticipating a traffic jam to leave on morning's first high tide. But all the other sailors were hanging around for a cocktail party that night with Juan Carlos, the Spanish king du jour. Not impressed by royalty, we stayed on task and, by default, became the only boat to depart Palos that morning, August 3, 1992. A bragging point.

The first leg for Columbus (and for us) was about 900 miles of open ocean to the Canaries. On August 9, he made landfall at Gran Canaria, one of the seven big islands in the chain. That same date, 500 years later, so did we.

Columbus spent a whole month in the Canaries, mostly on another island, Gomera.

Bet your 4th-grade history teacher didn’t tell you this: Columbus had had a mistress back in Spain! He likely saw her again when he reached Gomera. After their fling on the mainland, she had married the now-deceased Governor-General of the Canaries and was now a 27-year-old widow, 900 miles from Spain. Columbus, 41, also widowed, and also 900 miles from Spain. So what do you think happened?

An old painting shows her beauty. Her name was Beatrice.

It might have been a nice reunion and sad parting before Columbus set sail into history.

Some historians believe Beatrice and Christopher were in a relationship that only ended when Columbus died in 1506 at age 55.

I was borderline obsessive on how closely we were mirroring the Columbus adventure, so it was a bonus when we ran into a beautiful young Spanish woman when docked in Las Palmas. We invited her (and her handsome young boyfriend) to come aboard for a glass of Diego, excellent white wine from Tenerife. When we asked her name, she smiled, black eyes sparkling: "Beatrice! My name is Beatrice!"

You can't make this stuff up!

Our voyage continues in this space tomorrow. We'll cast off from the Canaries for a long sail to the New World, following Columbus across the Ocean Sea.

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