Viewing a world-famous sailing yacht might not be on everyone’s “Bucket List.” In the United States sports landscape, sailing has never had the wildly popular following enjoyed by football and baseball. And to many non-sailors, watching a sailboat carefully navigate a race course is about as exciting as watching paint dry.
But being in the presence of an America’s Cup yacht is an extraordinary experience. Back in 1990, my husband Mark and I were living just south of Annapolis, Maryland (often called the United States’ Sailing Capital). The entire town revolves around sailing, with hundreds of boat slips and several Wednesday night racing series every year. We were on the edges of the “sailing crowd,” as we participated in weekend cruises with a very large Chesapeake Bay sailing club.
We also knew the Annapolis’ sailing scene’s “movers and shakers,” a few by their first names. In fact, our friend Jim Kavle crewed on Dennis Connor’s “Stars and Stripes” America’s Cup defender yacht in 1988 (and they won!). So when we heard that the J-Class Yachts Endeavour and Shamrock V would visit Annapolis and Baltimore before a sailing regatta off Annapolis, we moved this event to the top of our personal “bucket list.”
In 1934, the 130-foot J-Class yacht Endeavour was launched to compete in that year’s America’s Cup. Sir Thomas Sopwith, a British yachtsman and aviation entrepreneur, integrated aviation Technology into the vessel’s sailing rig and winches.
After competing against fellow J-class yachts Shamrock V and Velsheda, race-winning Endeavour challenged Rainbow for the 1934 America’s Cup in Newport, Rhode Island. Although Endeavour didn’t win the Cup, she made the strongest second-place finish of any J-class yacht in history. Next, she successfully raced in England before being docked before World War II.
Following the war, Endeavour acquired a series of owners and just escaped the scrap yard several times. In 1984, Elizabeth Meyer, a visionary American yachtswoman, bought Endeavour and treated this grand old girl to a five-year restoration. In June 1989, 52 years after her last race, Endeavour sailed once again.
Shamrock V, the first UK-built J-class yacht, was launched in 1930. Sir Thomas Lipton (think Lipton Tea) commissioned the 120-foot wooden vessel for the 1930 America’s Cup Challenge (his fifth one). Unfortunately, he didn’t win and passed away in 1931. Sir Thomas Sopwith (Endeavour’s owner) purchased Shamrock V to race against his other yacht. Shamrock V later passed through several more owners and name changes.
Finally, Shamrock V passed to a knowledgeable British yachtsman in 2022. This striking J-class yacht received a much-deserved restoration, the most extensive one since her launch nearly 100 years before.
From our earliest days together, my husband and I have moved mountains, and traveled considerable distances, for epic viewing experiences. Living in eastern North Carolina, we heard about the last day of the Monet exhibit in Raleigh ─ two hours away. It was worth the aggravation to see this world-class artwork.
Viewing the J-class yachts Endeavour and Shamrock V is certainly in that league. During the third week of May 1990, we heard some Annapolis-area scuttlebutt (sailor talk for “gossip”) that these magnificent J-class yachts were on an East Coast tour. They were scheduled to visit Annapolis and Baltimore the next day.
The yachts would be on the United States Naval Academy seawall the next morning, and they would be viewable until about lunchtime. Then, Endeavour and Shamrock would briefly visit Baltimore’s Inner Harbor. Finally, the yachts would sail back to Annapolis to prepare for an upcoming regatta (race).
We knew this was the chance of a lifetime. We would probably never see these two magnificent yachts together again. We immediately changed our plans, gearing up to hit the Naval Academy seawall bright and early the next morning.
After parking the car outside the Naval Academy grounds, we entered the campus and headed toward the seawall. We could easily see Endeavour’s and Shamrock V’s masts towering over the buildings and trees. On that Chesapeake Bay spring day, the warm sunshine was quickly drying up the morning dew.
Arriving at the seawall, we stopped in our tracks. Just a few yards away, the beautifully restored Endeavour and Shamrock V proudly showed off their spotless decks and polished wooden brightwork. The paid crews had tidied up the yachts’ decks, and the sails were neatly flaked (organized) so they could easily be raised again.
By any account, Endeavour and Shamrock V are in a class by themselves. We were mesmerized by the sheer size of these vessels. In fact, Endeavour’s then-owner Elizabeth Meyer had her picture taken as she sat atop the four-foot-wide boom ─ on a rocking chair. This well-heeled businesswoman (and yachtswoman) had both yachts completely restored so they could return to their former glory.
Both sailing yachts’ beefy rigging is now complemented by hydraulic sail-handling gear ─ the only way to safely handle these massive sails. Both sailing vessels carry a professional captain and crew.
We kept thinking we should leave, but we couldn’t tear ourselves away from classic yacht history. Finally, we walked back to the car ─ and I kept turning around to glimpse those massive masts one more time. Later that morning, we hopped in the car and headed to Baltimore, about an hour away.
After parking near the Inner Harbor, we walked down to Harborplace at the water’s edge. And right on schedule, Endeavour and Shamrock V glided through the water in front of the National Aquarium in Baltimore. The water was like glass, casting a reflection of the yachts’ sails as they slowly motored around the Inner Harbor. Finally, Endeavour and Shamrock V set a course back to Annapolis for the regatta ─ ready to take their place in J-class yacht racing history.
In October 1989, Endeavour and Shamrock V launched a series of regattas off major East Coast ports. The Manhattan, Annapolis, Boston, Marblehead, and Newport regattas drew hundreds of thousands of shoreside spectators.
From 1989 to 1999, Endeavour toured the East Coast and Caribbean while engaging in high-profile races. And in April 1999, The J-class yachts Endeavour, Shamrock V, and Velsheda competed against each other in the Antigua Classics Regatta. Finally, in June 2017, Shamrock V sailed in Bermuda’s America’s Cup J-Class Regatta. Six other J-class yachts (including newer yachts) joined the largest-ever fleet.
In 2026, J-class yachting activities are concentrated in European waters. Looking ahead to the Louis Vuitton2027 America’s Cup in Naples, Italy, Shamrock V has been invited to anchor the event. As the oldest existing America’s Cup yacht, she will introduce a new generation of sailors and spectators to epic viewing experiences.
