All-women’s club sails into their 50th season

An all-women’s club has been sailing the waters around Sarasota and Longboat Key for 50 years, but somewhere along the line Luffing Lassies became a more suitable name than the original, Sarasota Sailing and Sinking Society. 

Luffing means to head a boat up into the breeze and is a much more apt moniker for this group that not only enjoys the wind-driven, nautical pursuit but also teaches it to newcomers every September during a two-week Introduction to Sailing course. 

“A lot of times, women crew for their husbands or boyfriends or on other boats,” Donna Hillmyer said. “With this, you are the one driving the boat, going where you want to, and it’s your challenge that you’re taking on. It’s really empowering.”

The first week is spent on the basics. The second prepares prospective Lassies to race. The Lassies operate under the larger umbrella of the Florida Women’s Sailing Association, and every Thursday during race season, they race a different club from the association. 

Some Lassies start off knowing how to sail, while others start from scratch. But they all have to attend the learning sessions. 

“We like them to come in for these two weeks because they create a bond with those women. The camaraderie is just stronger.” Hillmyer said. “It’s like going through hell week together. They have a really good time.”

The first day takes place under the pavilion at the Sarasota Sailing Squadron, the Lassies' home base on City Island. Prospective Lassies rotate through three stations on land before hitting the water for a swim test. 

Lassies learn to sail on Sunfish, personal-sized craft with a single sail. One is set up on land, so the women can learn how to hold the tiller, which steers the boat. Another station is set up to learn how to tie sailing knots. And the final station offers practice on ducking under the sail when changing direction — or jibing.

After practice on land wraps up, the women are told to jump off the dock into Sarasota Bay, once wearing a life vest and once without. But the exercise is more than a test of basic swimming skills.

“It’s so we know and they know that when they hit the water, because you often swim more than you sail in the beginning, that they aren’t nervous and won’t react adversely,” Hillmyer said.

Carrie Seven moved from St. Louis, Missouri last year and is one of the 10 women enrolled this year. She heard of the Lassies in 2018 when her sailing club in St. Louis, the Flying Scots, participated in the squadron’s Midwinter Regatta. 

“I absolutely fell in love with the place,” Seven said, adding she had a Sunfish at home and was told about the local racing club. “I said that’s where I want to be in the next four to five years, whenever my boys are out of the nest.” 

The boys left the nest last year, and at age 51, Seven packed her bags for Sarasota.

Thirty women applied this year, but there were only 10 spots available. Some women realize before and during the classes that sailing isn’t for them, but the class size is intentionally kept small because it’s easier to teach a smaller group. 

Adding this year’s recruits to the roster makes a total of 100 Lassies. Ages amongst the group vary from the mid-40s up into the 80s. If a member can’t sail anymore, they can stay on as a social Lassie and continue to attend parties. Retired Lassies also have their own club called the Anchors. They meet for lunch once a month. 

Rita Steele, Hillmyer’s mother, has been in the club since 1979 and is still an active Lassie. But Steele hadn’t sailed a day before joining. During her first race, everyone else had made it through the course and were waiting to start the second race. 

“They came out and said you have to go back to the start, so that’s how I started,” she said. “So it’s possible for everybody to learn how to sail, and we have so much fun.”