Classic sailing with Jimmy Buffett on fast track to Key West

By Craig Davis, Craigslegztravels.com

Until Henry Flagler built his overseas railroad through the Florida Keys, the only way to get to Key West was by boat.

The Fort Lauderdale to Key West sailing race has been celebrating that heritage for the past 42 years.

In 1980, as a sports writer covering the race, an invitation to sail in the crew aboard Ticonderoga, provided a rare opportunity to make the journey to the southernmost city in one of the most storied ocean sailing yachts.

An unexpected bonus came upon boarding before the race in Fort Lauderdale and discovering that Jimmy Buffett was also part of the crew.

At the time, Buffett was synonymous with Key West and sailing. But on this voyage, the undisputed rock star was Ticonderoga. Buffett, the renowned son of a son of a sailor, was as enthralled by L. Francis Herreshoff’s legendary yacht as the rest of us.

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Below is the tale as I reported it in January 1980:

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Singer/sailor Jimmy Buffett was perched on the bowsprit of the yacht Ticonderoga in a pose suitable for an album cover when a shackle on the mast snapped and the jib came tumbling down.

Rudely awakened from his shipboard reverie, Buffett, the king of Margaritaville, reacted like any good deck hand would and began hauling in the wildly flapping sail.

With help it was soon under control, but the big old ketch had lost considerable speed without the driving force of its forward sail.

A couple of other boats in Ticonderoga’s class in the Fort Lauderdale to key West Race were already pulling away. It was Thursday morning and the 160-mile chase was barely underway with the aid of a firm northeast breeze under a pure blue sky on a placid, sparkling sea.

“I was just sitting up there daydreaming and I saw it let go,” Buffett said as he watched crewman Joey Tress climb hand over hand up the shrouds of the 85-foot main mast to retrieve the jib halyard.

Tress grew weary upon reaching the top and the mainsail had to be dropped and a boatswain’s chair hoisted to bring him down.

The incident sapped valuable time which contributed to Ticonderoga’s seventh-place finish in Class A of the Performance Handicap Racing Fleet. But as soon as another sail was set, the 72-foot ketch began gaining on her rivals.

All day long the majestic sailboat roared through the fleet, passing boats that had started earlier, eliciting waves and compliments as she has throughout her 43 years at sea. Big Ti eased into port well before dawn Friday, turning in the third-fastest elapsed time among the 111 boats in the race.

“I haven’t been in Key West in over a year. I can’t think of a better way to go back than to arrive on Ticonderoga,” said Buffett, a Mobile, Ala., native that most pop music fans associate with Key West. He had an apartment there during the struggling years of a career that has since blossomed magnificently.

Indeed, he couldn’t have picked more suitable means to a homecoming. Ticonderoga is considered the finest achievement of legendary yacht designer L. Francis Herreshoff. Though built for luxury ocean cruising, it has amassed a history of ocean racing excellence perhaps unparalleled.

During its competitive prime in the 1960s under then-owner Robert Johnson, Ticonderoga held more than 30 race records, many of which still stand. Its greatest moment came in the 1965 transpacific race to Hawaii when Big Ti averaged more than nine knots in breaking the record for the 2,225-mile race that had stood for 10 years.

Since current owner Ken MacKenzie bought Ticonderoga in 1971 it has been used primarily for charters in the Caribbean.

“It’s a sweet boat,” Buffett said after taking a turn at the helm during the afternoon as the fleet began the arc around the Florida Keys.

“It’s nice to go fast like this and be comfortable. That’s why Herreshoff was such a genius. He built such fast, comfortable boats, from dinghies to this size.”

It would be difficult to find a comparable ride to that aboard Ticonderoga. It rambles over the waves with an amazing smoothness and simplicity of motion that makes its speed deceiving. With conditions moderate throughout the race, the boat never seemed stressed in any way.

You can see the difference between sailing a small boat and sailing a boat like this,” said foredeck captain Pogo Evans as we passed another racer.

“They’re in rain slickers and we’re running around in shorts and T-shirts.”

Heading south and turning west toward his former home aboard such a majestic sailing vessel, Buffett was in his element. This is the nautical, tropical lifestyle the son of a son of a sailor made famous in song and spawned a legion of Parrothead followers.

“I really haven’t been sailing since August. Coming out today I realize how much I’ve missed it. And this is great. You don’t get these kinds of days too often,” he said.

Jimmy Buffett (center, standing) aboard Ticonderoga during the 1980 Fort Lauderdale to key West Race. (Craig Davis/Craigslegztravels.com)

Jimmy Buffett steers Ticonderoga during the 1980 Fort Lauderdale to Key West Race. (Craig Davis/Craigslegztravels.com)

Sun sets as Ticonderoga sails off the Upper Keys in the 1980 Fort Lauderdale to Key West Race. (Craig Davis/Craigslegztravels.com)

Jimmy Buffett is not your typical rock star. Stepping aboard in Fort Lauderdale dressed in shorts, a well-worn yellow shirt, boat shoes and bandages on his heels, he blended into the crew like just another deck hand. Experienced and knowledgeable, he jumped into action whenever MacKenzie called for a sale change.

As Ticonderoga pressed on with all sails tuned, Buffett sipped a beer and contributed a tale about gobbling Big Macs for breakfast in exchange for sea yarns. But there were no songs; Buffett was battling a cold.

Basking in the success of his latest album, Volcano, and winding down from a recent tour, Buffett was looking forward to delivery of a new wooden 26-foot sloop patterned after Herreshoff’s last private yacht. He plans to cruise alone on it in the Exuma chain of the Bahama Islands next spring and work on another album.

“Out sailing like this is the only time I can get away by myself and relax. It’s the catalyst that makes me work,” he said.

But as the sun sets over the Florida Keys, Buffett has fallen in love with Herreshoff’s best-known boat, just like everyone else who’s ever sailed on it.

Buffett sold his 54-foot ketch Euphoria more than a year ago and is intrigued by the knowledge that Ticonderoga is for sale.

“It I ever thought about getting another big boat, both for the way she sails and the history behind her, Ticonderoga is the boat I’d like to someday own,” he said.

Just think of the stories this old vessel could tell. Must be enough to fill a career’s worth of albums.

 2018 update

As years passed, Jimmy Buffett was quoted often about his admiration for Ticonderoga. In his autobiography, “A Pirate Looks at Fifty,” he wrote that the Chart Room, the famous bar at the Pier House in Key West, was where “I almost bought Ticonderoga, the boat of my dreams, from Ken MacKenzie for an amazingly low price.”

Herreshoff’s masterpiece underwent a major rebuild in the late 1980s, and now 80, is still sailing and occasionally raced by current owner, Connecticut Senator L. Scott Frantz. According to published reports, Buffett was among the bidders before Ticonderoga was sold to Frantz in 1993.

During its peak years in the ’80s, the Fort Lauderdale to Key West Race had well over 100 boats making the 160-mile annual voyage. Part of its popularity had to do with the weekend-long bacchanal in Key West harbor that followed the race. Notable in the aftermath of the 1980 race was Buffett jumping on stage with the house band at the Pier House for an extended Saturday night closing set.

Participation in long-distance offshore racing has diminished, but the 42^nd Fort Lauderdale to Key West Race set sail on Jan. 10, 2018 with 31 boats listed on the entry list.

Sailing is still an integral part of the Key West scene, particularly the sunset cruises. Here are the top 10 Key West sailing and water cruises.

Sept. 2, 2023 update