Labor Day Regatta celebrates its 75th year under sail

By Ian Swaby
| 5:00 a.m. August 31, 2023

The 75th Annual Labor Day Regatta will be held Sep. 2 and 3.

Sarasota
Neighbors

As the public gathers on the shores to view the Annual Labor Day Regatta, many viewers can often be heard reminiscing about their childhood experiences in the event, which dates back to 1946, said Regatta Chair Dave Hillmyer.

Held by the Sarasota Sailing Squadron, the event, which the organization says is the oldest continually held regatta in the southeast, will host competitors ranging from 7 years old, to about 70, during its 75th anniversary this year on Sep. 2-3.

Canceled only three times in its history, the event maintains a steady popularity, drawing clubs from across Florida from areas like St. Petersburg, Davis Islands in Tampa, more distant locations such as Jacksonville, and even some individuals from other states.

“Everybody just knows about this regatta,” Hillmyer said. “This is such a historic sailing venue.”

Calling sailors young and old

While the regatta originally featured about 50% adults, the last few years have been youth-focused, with about 150 kids signed up out of 175 competitors this year, Hillmyer said.

He said the occasion, which involves four different race courses in the bay, as well as racing closer to shore for the youngest participants, holds particular importance for youth.

For some younger people, it’s the first regatta of the school season, while for other kids, it may be their first regatta ever.

“This is the first time that they get to put their skills to the test on the water,” he said. “It’s kind of a big deal.”

Kay Brunsvold gets ready to set sail in the 68th annual Labor Day Regatta.

Dave Hillmyer and his wife Donna Hillmyer, who have both been involved with the club since about age 10, are no strangers to youth sailing, but they've also had the chance to watch other participants enjoy an experience similar to their own.

“We watch these kids like we follow them throughout their lives,” Donna Hillmyer said.

Yet the event excites adults as well; an inaugural sailing event, of sorts, for the fall season, it follows the relative lack of activity during the heat of summer, Dave Hillmyer said.

What really makes the event special, said Hillmyer, is the amount of volunteers it receives.

None of the individuals assisting with the event, which includes about 40 on the water and 100 on land, are paid, he said.

Volunteers will staff the 15 to 16 support powerboats and will also help on shore through activities like serving food and drinks, monitoring parking, or taking out trash.

He believes participants will have a pleasant experience out on the bay or at the squadron's clubhouse on City Island, where it has leased the land from the city of Sarasota.

“Out in the middle of the bay, you don't see a lot of boat traffic, so it's really nice,” he said.

He said members have even camped out at the clubhouse site in the past.

“I think people find it very comfortable here because we have such a low- key atmosphere."

Although there are other labor day events, such as a Labor Day night race on Davis Islands, the Sarasota event holds a special meaning for the public, he said.

“Everybody knows if you say 'the Labor Day Regatta' in Florida, it means Sarasota Sailing Squadron."

Select events from the history of the Sarasota Sailing Squadron

Source: “The History of the Sarasota Sailing Squadron” by John Pether

Late 1930s

The squadron is formed by a group of young Sarasota men, partly as an extension of the Sarasota Yacht Club and partly by those who cannot afford the cost of membership in the organization.

1942

The squadron becomes inactive with the onset of World War II, with many members leaving to participate in the war.

1946

The squadron is reactivated under the local YMCA. It hosts its first Annual Labor Day Regatta, drawing over 100 boats from the east and west coasts of Florida and over 5,000 spectators.

1948

During the annual regatta, a ketch (a type of two-masted sailboat) called Bonnie Kaye, runs aground on a sand shoal and sinks. Its owner, Matthew Van Leeuwen, a World War II veteran who lived aboard the vessel and wore an artificial leg, loses his money and possessions and survives by clinging to a buoy overnight. Squadron members and other sailors begin a fundraising drive for Leeuwen.

1950

The fifth annual regatta is canceled due to strong winds and rains from Hurricane Easy, although the year is still counted toward the total number of regattas.

1957

As the city of Sarasota expands, preparing to demolish the city pier, the club plans a relocation to its current home of City Island. The City Commission instructs the city manager and city attorney to negotiate a contract with the squadron making the northeast corner of City Island available to boating groups.

1958

Construction on the original clubhouse begins. Due to several members who are employees of Florida Power & Light, eight FPL light poles are used to build the clubhouse, which at the time had only a roof, while more FPL poles are used to build the original dock.

1960

By this time, the regatta is recognized by the United States Yacht Racing Union.

1961

During the 16th annual regatta, a major storm suddenly capsizes 55 boats.

1967

Planning for a new clubhouse begins. Among the renovations are an additional wing, a new roof, enhancements to the stone house, and the relocation of the hoist.

1972

Member Lilly Kaighin arrives in Sarasota from Tampa. Shortly thereafter, she would convince a group of six members to found the women’s sailing group “Sarasota Sailing and Sinking Society,” which quickly expanded in size and was later renamed to “Luffing Lassies.” The organization is still active today.

1976 to 1978

Amid dropping finances and attendance, the club enters a phase of relative inactivity, becoming primarily a storage facility for boats.

1978

Member Pat Murphy, who joined the club at age 13, accepts the role of commodore following his proposal to reinvigorate the club, which includes restarting its youth sailing program and opening every Saturday and eventually every Sunday.

1980

The Sarasota Sailing Squadron is incorporated as a 501(c)(3) nonprofit organization.

1984

Susan Pether is elected as the first and only woman commodore in the history of the squadron. She bans alcohol at board meetings, increasing the productivity of discussions.

1985

The 40th Annual Labor Day Regatta is canceled due to Hurricane Elena, amid storm evacuation orders.

1992

The club’s pavilion is rebuilt, serving as the location for the marriage of club manager Pat Murphy to Dona Worley.

1994

A race to Havana, Cuba, is initiated by member Bob Winters, stirring controversy. As boaters arrive in Havana, they discover the race was a front for selling participants special memberships to Club Náutico, a yacht club in Havana partially owned by the Cuban government. Winters had an agreement with the Cuban government that allowed him to stay in the country to avoid the bankruptcy of his business and criminal charges of pocketing money from boat sales.

2001

The club’s new porch is installed.

2003

Chris Branning is nominated as the club's top youth sailor of the year. The nomination allows him to compete in the ISAF Youth World Championships and the U.S. National High School Singlehanded Championships. He also goes on to race in over fifty major sailboat races, serving as navigator and winning first place in a majority of cases. In 2007, he serves as the navigator of a Disney-sponsored team aboard the 52-foot ocean racer Morning Light. He is later featured in the 2008 sports documentary "Morning Light," produced by Walt Disney Studios Motion Pictures.

2018

The annual regatta is cancelled due to severe red tide.

author

Ian Swaby

Ian Swaby is the Sarasota neighbors writer for the Observer. Ian is a Florida State University graduate of Editing, Writing, and Media and previously worked in the publishing industry in the Cayman Islands.