- April 30, 2025
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Looking north while crossing the Ringling Bridge toward St. Armands is often a familiar sight: dozens of tiny sailing dinghies just off the shore of City Island.
They are the training boats Sarasota Youth Sailing uses to teach young captains how to tack, jibe and safely navigate open waters in the protected environment of Sarasota Bay, just as the youth program of the Sarasota Sailing Squadron has done since the late 1970s since its founding by the Luffing Lassies, the squadron’s women’s sailing group.
The organizations separate yet intertwined, Sarasota Youth Sailing has embarked on the city approval process to build a new education building to replace its non-climate-controlled, warehouse-style building with a two-story structure of approximately 3,000 square feet on the open-air ground level for storage beneath 1,895 square feet of meeting space, offices and restrooms.
It appeared before the city's Development Review Committee as a new submittal on March 19.
The office space is currently an RV, according to project architect Derek Pirozzi, and among the notable aspects of the building design are dual "double butterfly" roof structures directing rainwater into a cistern, which will be used to wash boats.
The SYS program occupies 1.39 acres of the overall 6.2-acre Sarasota Sailing Squadron site.
But first, in order to justify the expense of the $3 million project, plus another million dollars that needs to be invested in storm damage repairs to the city-owned property, the organization recently sought a lease extension of 30 to 50 years from the city.
Unanimous approval of the Sarasota City Commission extended the lease for 30 years, through November 2055, on March 3.
Sarasota Sailing Squadron sought the extension before allocating more than $350,000 for repairs and upgrades over the next six months and anticipates a total investment of 4.1 million over the next two to five years, including the SYS center and replacement of the wave fence along the shoreline destroyed during the 2024 hurricane season.
“We bring in people from all over the world to come and see Sarasota,” Squadron Commodore Bob Twinem told commissioners of the organization. “We did suffer quite a bit of damage to the buildings, the grounds, the docks, and we need to invest quite a bit of money into that.”
The Squadron is up and running, Twinem said, but to justify the capital outlay the lease extension is necessary. “Also, in our lease, it says if you spend over a certain amount of money, there might be an opportunity to extend the lease,” he added.
Vice Mayor Debbie Trice wanted assurances that, because of the length of the extension, the lease was non-transferrable. Wayne Appleby, the city’s economic development manager, did confirm it.
In motioning to approve the lease for 30 years during the March 3 meeting, Commissioner Kathy Kelley Ohlrich said she was comfortable with the terms, and the longevity of the Sailing Squadron, which was founded in the 1930s at the city pier, the current site of Marina Jack.
“Sarasota Sailing Squadron is not going anywhere. They're not going to pick up all those boats and those buildings and move,” Ohlrich said. "Everybody who sees the joy in the work that's being done appreciates it. The regatta, the youth programs, visitors see those little boats floating around in the water and even if they don't sail, they like it. Our responsibility is to do what's right for the city as well as do what's right for the Sailing Squadron, and I think this does it."
The rental amount is based on membership, most recently ranging from $59,091 per year in fiscal year 2022 to $68,218 in fiscal year 2024.
Funding construction of a new education center and repairs not insured — the wave fence, for example — requires funding. Currently, a 501(c)7 organization, Sarasota Sailing Squadron, can operate a capital campaign, but donations are not tax deductible.
“Some of the things we need to repair we can't pay for out of our dues,” Twinem told the Observer. “We need to raise money to do that.”
Although Sarasota is well known for its philanthropic largesse, tax deductibility is essential to giving. As a result, Sarasota Sailing Squadron is exploring how to best convert the organization to 501(c) 3 status. Currently, making tax-deductible donations to another sailing-centric organization, Sail Sarasota, can then transfer the gifts to the Squadron. Twinem said discussions are underway to potentially merge the two organizations or to convert the Squadron to a 501(c) 3.
“Our mission stays the same, but right now we can't raise tax-deductible donations for building the wave fence and for the Sarasota Youth Sailing building,” said Twinem, who sits on the boards of both the Squadron and SYS. “We’re going to raise millions of dollars for that. We just have to weigh out how that all ties in together. When we first went through the hurricanes, we reached out to people and said if you're donating and you're itemizing your deductions, send it to Sail Sarasota and specify it's for dock repair, and then they give money to us.”
Much of the damage was non-insurable, specifically anything in the water such as the docks and wave fence, a structure located beneath a pier critical to protecting infrastructure as well as sailers by breaking wakes from powerboats traversing the channel between St. Armands and Longboat Keys.
With all the challenges, Twinem said he signed up to be commodore “probably at the wrong year, but it’s a great, resilient group of people. We really are focused on growing what we have now as opposed to just coasting along.”
