Regatta has Sailed Yearly, Except Once, Since 1946
Articles: Sarasota History
The Labor Day Regatta has been an institution in Sarasota since 1946, with Hurricane Elena in 1985 causing the only break in the series. The first post-World War II regatta included competitions for boats in moth, snipe, cricket and suicide classes. There also was a free-for-all.
The Sarasota Herald-Tribune described a novel race called “b’ang and go back,” which required boats to keep under sail and head out from shore without stalling and, upon the firing of the gun, turn around and race back to the starting point. There were few Sarasota winners that year.
The sailing regatta was only one of a number of events in the 1946 Labor Day weekend celebration. A dance, bicycle rodeo, speed boat demonstration, water carnival at the Lido Casino pool and “Shipwreck Follies” at the Municipal Auditorium rounded out the activities. The Follies included dance routines, acrobatics, comedy acts and modeling of fashionable beach wear by senior girls from Sarasota High School.
The following year the regatta, sponsored by the Sarasota Sailing Squadron, mushroomed in size and scope. In a preliminary event, cruisers from a number of Florida cities raced from Tampa to Sarasota between 6:00 p.m. Saturday and 6:00 a.m. Sunday. The primary races on Sunday attracted more than 100 boats in six classes competing for 26 trophies.
A barbecue lunch, provided by the Sailing Squadron, was available at the waterfront park adjoining the city pier for all participants and visiting yachtsmen. Spectators who watched from the pier were provided with bleachers and a sound system. The Herald-Tribune estimated that 5,000 watched from shore or water as seven Sarasotans won trophies.
Joseph Steinmetz took this photo of the 1952 regatta from the top of Sarasota’s Orange Blossom Hotel on the south corner of Main Street and Palm Avenue. The view of Sarasota Bay overlooks the Hover Arcade, which housed City Hall, and the Municipal Pier. (The Sarasota Chamber of Commerce is hidden by trees on the south side of the pier). A relatively un-populated Golden Gate Point juts into the bay at the upper right. Siesta Key, Big Pass and Lido Key line the horizon.
For this Seventh Annual Regatta, 100 boats from 15 Florida yachting organizations competed in races for 10 classes. Six Sarasotans took home first, second, or third-place trophies. For the preliminary race 11 cruisers, one locally owned by Dr. A.L. Matthews, sailed from Tampa to Sarasota between Friday night and Saturday morning.
Sailing enthusiasts can look forward to the Sarasota Sailing Squadron’s 49th Labor Day Regatta* this weekend.
*Editor’s note: This article was published in 1995; this year's Labor Day’s Regatta was its 70th annual event.