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Lilly Kaighin Memorial Regatta

Established 1999

Lilly Kaighin sailing her sunfish_edited

Lilly Kaighin started the Luffing Lassies in 1972.  She gathered up a few friends to climb on board and set sail to what would become one of the premier women’s sailing organizations in the state of Florida.  And so, we take a day out of our year to honor our founder by having the Lilly Kaighin Memorial Regatta and to celebrate her legacy.


The Luffing Lassies’ Annual Lilly Kaighin Memorial Regatta was established in 1999.  This regatta is held around November 13th of every year since Lilly’s passing in remembrance of “Lilly Kaighin Day”.  The original “Lilly Kaighin Day” was announced at the Luffing Lassies’ 25th Anniversary Celebration in 1997 and was awarded to Lilly by then mayor of Sarasota, Molly Cardamone, who was also a former Luffing Lassie.  It was recognized as a “day of special importance that is worthy of the citizens of Sarasota” to “proudly honor one of its citizens, Lilly Kaighin, for all of her notable achievements” including:  

  • Founder of the Luffing Lassies (1972)

  • Co-Founder of the Dinghy Dames

  • First Captain of the Luffing Lassies (1972) and again in (1977)

  • Two-Time Winner of the Florida Adam’s Cup Championship (1974 & 1980)

  • Very First Recipient of the Bankston Trophy for the Florida Women’s Sailing Association (FWSA) Championship Regatta (1976)

  • Six-Time Winner of the FWSA Championship Regatta Bankston Trophy in Spinnaker Class (1976, 1977, 1978, 1980, 1986, & 1988)

  • Founder & 1st President of PALS, which is Partnerships and Alliances Linking Schools (1980)

  • President of the Junior League of Sarasota (1984)

  • President of Florida Women’s Sailing Association (FWSA) (1988)

  • Chairman of the Town Hall Series for the Ringling School of Art and Design Library Association (1994)

  • Awarded Junior League Sustainer Community Service Award (1994)

  • Awarded the Crystal Heart Award from Girl Scouts for her service to the community (1996)

  • Founder of the Ding-A-Lings, a musical group, made up of Luffing Lassies (1997)       


The Lilly Kaighin Memorial Regatta is a special day for all Luffing Lassies.  It celebrates its founder by having its Active members participate in a typical day of competition on the water by racing in a Clearwater Pram (the “boat of honor” for the regatta as it was the original boat of the Luffing Lassies), a Sunfish (the main boat of the Lassies today), or in a 420 (a 2 person crewed boat).  And the course is the original one that has been sailed by the Lassies for over 45 years – Modified Olympic for the Sunfish & 420 Fleets and a Triangle for the Pram.  It is a day filled with camaraderie, good competition, special trophies, and a luncheon provided by the Luffing Lassies to celebrate the day.  In keeping with the competitiveness of the Lassies, the races for this regatta also count towards the Luffing Lassie Series.  


The beautiful perpetual trophies were hand-made by Lilly’s oldest son, Jim Kaighin, in Marsh Harbour in Abaco, Bahamas.  And the individual trophies are typically made by a member of Lilly’s family and are definitely made with a lot of love.   


Active Lassies, Social members, Anchors, and members of Lilly’s family join in the festivities to honor Lilly’s memory.  We come together to celebrate with all who continue to make the Luffing Lassies exactly what it was meant to be – a day filled with good friends, good competition, lots of laughter, and making memories that will last a lifetime.   


Thank you to all that participate in the Annual Lilly Kaighin Memorial Regatta.  You are an important part of Luffing Lassie history and are appreciated for your part in continuing the Luffing Lassie legacy and for keeping wind in its sails!  

Lorri Kaighin, Regatta Chair

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