Betty Ann’s maiden voyage, from Bradenton, Florida to Point Judith, Rhode Island in the Spring of 2004, was one of her more difficult trips. Unfortunately, it was also the trip that we hoped to make a sailor out of one of Archie’s granddaughters.

As far as I know, the first leg of the trip went smoothly, with Archie and his friends Denny and Ken sailing overnight along Florida’s western coast and making landfall in Key West. It’s probably safe to say that they had a very good time in Key West. It’s kind of hard not to do so. This was probably the trip that Archie discovered Blue Heaven, his never-miss restaurant in Key West, where you eat under the stars and the pecking chickens mingle with the patrons.

Archie was joined by his second crew in Key Largo. The crew included:

• Archie’s daughter-in-law Laura, who has sailing deep in her bones from a childhood of sailing;
• my friend Bill, who has lived his whole life in the sailing town Marblehead, ran a launch for years, and sailed his own sailboat north from Florida;
• Kelly, Laura’s 14-year-old daughter and Archie’s granddaughter; and
• me (Mike), who had crewed on Bill’s boat on that sail up from Florida, so had some sense of what to expect.

Out of Archie’s seven grandchildren, Kelly was our great hope for a sailor in the next generation. While the other grandkids have lots of interests — running, singing, surfing — sailing doesn’t hold much appeal for them. At age 14, Kelly was a highly competitive downhill skier with a daredevil attitude. She seemed the type who might love the challenge of sailing hundreds of miles offshore in the Gulf Stream.

Unfortunately, our hopes of making a sailor out of her ran smack into a cold north wind. The Gulf Stream flows like a river in the ocean, except it has no banks and moves far more water than all the rivers on earth combined. In good conditions, sailing north in the stream is a pleasure:  the air feels velvety warm, the current adds 2 to 3 knots to your speed, flying fish whiz through the air, and dolphins play in your bow waves. But the Gulf Stream in a stiff north wind is another story. A north wind blowing over a north flowing stream creates a short, choppy and (most fatally) disorganized sea.

Within hours of leaving Key Largo, we were slogging head on into the wind through a very unsteady chop. The sky was grey, the wind chilly, and the motion most unpleasant. Before long, Kelly was sick and miserable. By the time we were off Miami, most of us had followed suit. One night far out in the Gulf of Florida, off Georgia, we were hit suddenly and hard by a fast-moving squall with 60 mph winds. Both Laura and Kelly were thrown from their berths against their cabin walls. This was not the salubrious Florida vacation any of us envisioned.

Despite the cold wind and stiff chop, we had some good times on the voyage — particularly when we were sailing into the ports Fort Lauderdale, Ponce Inlet and Beaufort, North Carolina! Even Kelly found some joy in re-reading all of the then-published Harry Potter books.

Happy and perhaps a bit relieved, we left Archie in Beaufort, where he was joined by his next crew. Bill enjoyed the trip enough that he has never missed sailing at least one leg of Archie’s north-and-south trips in the many years since. Kelly, on the other hand, has been busy with many other adventures — none of which involve a boat and a sail. In retrospect, maybe an offshore trip from Florida to North Carolina was not the right “starter trip” to make a sailor.

Then again, if the sun had shone, the wind had been a gentle and steady southwesterly, and the dolphins had been particularly playful, we might have well hooked her on sailing. Just maybe, instead of studying hard as a first year student at NYU Law School, Kelly might be bumming around the Caribbean, crewing on boats, listening to Jimmy Buffet and Jack Johnson, and drinking frozen Margaritas. Now that would make a grandfather proud.