I never met Jimmy Buffet, but I wrote about him.

“Buffett was the muse, the piper who led sailors and wannabe sailors to the Caribbean to rent sailboats and live the dream.”—Full and By September 2018

Buffett’s death five years after that was written struck a sad chord with sailors who considered themselves kindred spirits rather than just fans.

A few of them were waxing nostalgic at a yacht club gathering about Buffett and sailing adventures accompanied by his songs when someone mentioned a mutual acquaintance who claimed to have met him in the Caribbean. The claim was sketchy at best, but later it inspired the First Mate to propose that for the fun of it we each list the famous people we had met. 

I came up with a paltry two. The First Mate one-upped me with three, but later she looked up from her iPad and exclaimed, “You forgot Walter!” In her nightly cruise through the internet, she had come across a fuzzy black-and-white rendition of a SAILING Magazine feature published in 1980, and in one of the photos, there I was—with Walter.

Walter was Walter Cronkite, legendary journalist, anchorman of the CBS Evening News and, according to an opinion poll, “the most trusted man in America.” Maybe he didn’t make my list because when I met him he displayed none of the trappings of celebrity. Wearing seasoned leather Topsiders and a polo shirt embroidered with the name of his Westsail 42 yawl Wynte, he was just a fellow sailor.

Walter and I met in the warm breezes of Grand Bahama island because an idea cooked up in the northern latitude offices of SAILING Magazine somehow metamorphosed from wacky to brilliant.

At a typically unscripted staff meeting, the magazine’s then-advertising director threw out an idea he said would be a fabulous way to engage readers and impress advertisers. All we had to do was organize a regatta in a tropical locale featuring one-design sailboats sailed by the country’s best racing sailors as skippers with SAILING readers as crew.

After rolling my eyes, I pointed out the reasons this would be impossible to pull off, including extravagant cost and the unlikelihood of getting top sailors together for racing that had no class championship significance, not to mention the challenge of choosing the readers who would be their crews.

By nature, ad directors are not fazed by negative responses (tolerance of which is a requisite for the job), and he wasn’t. Let me try, he said, and I said OK, now let’s move on to something realistic.

It turned out that what was realistic was the concept that had fantasy written all over it. Amazing things started to happen, like dominoes not falling but standing up one after another.

Holiday Inn, eager to promote its glossy new resort on Grand Bahama, signed on as a sponsor. Tartan Marine jumped at the opportunity to bring attention to its new 33-foot Sparkman & Stephens designed Tartan 10 by providing nine of the boats. And all of the eight all-star sailors we invited said they would be delighted to race with amateurs in a sunny, breezy venue.

By then, my initial pessimism had been thoroughly debunked, but one issue remained—how to recruit readers to crew for the stars. Well, this proved to be almost too easy—unless you counted the clerical labor of dealing with the thousands of applications we received to sail in what was to be called the SAILING Magazine Masters/Weekenders Caribbean Regatta.

I had underestimated our readers’ enthusiasm for their sport. More than 5,000 of them responded to an invitation published in a single issue of the magazine to apply for a crew berth. Their applications filled a big spinnaker bag, from which a minor celebrity, the mayor of Port Washington, Wisconsin, SAILING’s hometown, drew 32 names.

The 26 men and six women represented 19 states and ranged in age from 21 to 66. Most had some cruising or club racing experience, some were neophytes, a few had long sailing resumés, like the oldest sailor in the group, whose name was—no kidding—Josh Slocum, a bluewater sailor for 56 of his 66 years.

Four would crew for each of the “masters”—Buddy Melges, Robbie Haines, Gary Jobson, Ted Hood, Judy Lawson, Tom Blackaller, Dennis Durgan and Mark Ploch—on a rotating basis. 

All the moving pieces had somehow fallen into place, but still I wondered: Would inexperienced sailors, including some who had never sailed beyond quiet inland waters, be up to sailing in offshore conditions with demanding skippers? Would elite skippers who demand and usually get perfection from their crews be able to sail happily with men and women who might have never in their lives trimmed a spinnaker?

The answers were yes and yes.

The sailing was terrific, some of it in conditions breezy enough to add drama with wipe-outs and even a dismasting. The competition was fierce, with Haines, hard pressed by Melges, winning the five-race series. The camaraderie was remarkable, with the famous and the not-famous getting along famously as they indulged their love of sailing on the water and the after-racing parties on shore.

But what about Walter?

Knowing he was a dedicated sailor, I took a flyer and invited him to come to our regatta as a guest celebrity. To my astonishment, he accepted. He fit right in with the assembled sailors, obviously enjoyed their company and made the trophy presentation memorable with a handshake for the winners from the most trusted man in America.

Regarding my ridiculously short list of famous acquaintances, one of the two was Hugh Hefner. He was kind enough to invite me to swim in the pool at the Playboy mansion in Los Angeles, a sybaritic construct that resembled the Pirates of the Caribbean waterway at Disney World populated by Playboy Bunnies instead of pirates. That was nice of Hugh, but it didn’t measure up to trading sailing stories with Walter Cronkite.