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Sailing in the New Year in the Caribbean

The magic of St. Barth – one day you don’t know anybody, the next day you’re sailing to windward in 30 knots aboard a yacht like Altair, a spectacularly restored 130-ft gaff ketch designed and built by Fife in 1911.

latitude/Richard
©2008 Latitude 38 Media, LLC

You know how, famously, there is no "second place" when it comes to the America’s Cup? The same is true, at least in our opinion, when it comes to the best place for a sailor to spend New Year’s. It’s St. Barth in the French West Indies, and nothing else comes close.

Why? First and foremost, the sailing conditions are superb — at least for those who revel in very strong winds and full-on tradewind seas. And the temperature of the air and beautiful blue water couldn’t be better. You take a wave and you’re refreshed, not chilled.

Maltese Falcon dominated the outer-outer anchorage at Gustavia.

latitude/Richard
©2008 Latitude 38 Media, LLC

Of course, the sailing and water conditions are superb up and down the Lesser Antilles in the winter. What makes St. Barth different is that it has one of the greatest concentrations of spectacular sailing yachts in the world, from nearly hundred-year-old wood classics to the most sleek and modern. And people actually sail them.

When we flew in from St. Martin on Christmas Day, and the pilot was about to land on the postage stamp-size runway, the first yacht we saw was Tom Perkins’ Belvedere-based 289-ft Maltese Falcon. With her unique and distinctive Dyna-Rig, she was impossible to miss and quite a sight. And as evening fell, the red lights atop the many 100+ foot masts were a testament to the number of  other large sailboats in the anchorages.

The last we heard, Paul ‘Microsoft’ Allen had three ‘earth warmers’, Octopus, seen here, being the largest. It’s our understanding that the little helicopter on the bow is used to fly in rock stars who play on the boat.

latitude/Richard
©2008 Latitude 38 Media, LLC

Alas, although Falcon is the biggest of sailboats, she was nonetheless dwarfed by the likes of Larry ‘BMW Oracle’ Ellison’s 450-ft motoryacht Rising Sun, and Paul ‘Microsoft’ Allen’s 420-ft Octopus. Worse still, for New Year’s in particular, the number of mega motoryachts — aka ‘earth warmers’ — far exceeded the number of sailing yachts.

We don’t want to rag on everyone who chartered a mega motoryacht, as some of them are new to the water and just don’t know any better. For example, one evening we spent about half an hour in conversation with a guy on a bench behind all the big motoryachts at the quai in Gustavia. At first he allowed that he’d chartered one of the boats and was only on the bench because the boat’s rolling motion at the dock had made him queasy. Much later, he allowed that he was John Frank, and had won two Super Bowl rings catching passes from Joe Montana and Steve Young as a tight end for the 49ers. Unlike most former pro ball players, Frank slimmed down, became a doctor in San Francisco, and has since become a very successful doctor in New York City. Anyway, the next day he went sailing with Donald Tofias aboard the latter’s 72-ft Wild Horses, so there is hope for him.

What makes St. Barth really special at New Year’s is that on New Year’s Eve afternoon, Tofias and the skippers of about 30 other yachts, large and small, humble and magnificent, go at each other in the highly unpublicized 22-mile Around the Island Race. And that sometimes even novices get taken along as crew. For example, this year one guy who didn’t know a bowline from a buntline got a ride aboard the 145-ft gaff-rigged Elenora 5, truly one of the great yachts in the world. Even more amazing, we were trimming the jib top aboard the equally magnificent 1911 130-ft Fife gaff schooner Altair on the last leg of the race, and looked back to see Bill Lilly, a two-time veteran of the Ha-Ha with his Newport Beach-based Lagoon 470 Moontide, driving the great yacht. What was he doing there?!

Having just the week before cruised his Lagoon 470 cat Moontide from La Paz to Nuevo Vallarta, it’s hard to understand how Newport’s Bill Lilly suddenly found himself at the helm of a 130-ft gaff schooner.

latitude/Richard
©2008 Latitude 38 Media, LLC

At the end of the grueling race, it’s hard enough for everyone to drag themselves to the champagne awards ceremony, followed only a few hours later by the big New Year celebration at the dock. But most succeeded. Tom Reardon, skipper of the great 72-ft Herreshoff ketch Ticonderoga, was feeling his oats this year, so instead of just firing Big Ti‘s cannon once, he allowed pretty girl after pretty girl to shout "Fire in the hole!" then put the hammer down. There were all kinds of other fireworks, huge parties on the boats, booze and music everywhere. Better still is what there wasn’t — no bad vibes, no fights, nobody puking all over themselves.

We’re not suggesting there was any favoritism, but an inordinate number of young ladies in short dresses got to fire Ticonderoga’s cannon.

latitude/Richard
©2008 Latitude 38 Media, LLC

And what better way for a sailor to ring in the early hours of the New Year than with Jimmy Buffett putting in a surprise appearance at 2 a.m. with the house band at Bez Bar? Now in his early 60s and looking particularly happy and healthy, Jimmy played rock ‘n roll classics with gusto, and the 100 or so people there joyously sang along. Our favorite was his classic ‘Autour de Rocher’, about the little hotel he used to have an interest in on St. Barth. "It was a very strange place," he told the crowd, "as it only had three rooms but had a bar as big as an aircraft carrier."

Although no longer a kid, Jimmy Buffett nonetheless played with childlike enthusiasm.

latitude/Doña de Mallorca
©2008 Latitude 38 Media, LLC

We don’t know how it would be possible, but we hope your New Year’s was as enjoyable as ours.

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