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Longboat friends take a surprise pirate cruise

Tennis enthusiast raises money for the Red Cross with a secret trip for her friends.


  • By Eric Garwood
  • | 7:09 p.m. April 1, 2022
  • Longboat Key
  • Neighbors
  • Share

Karen MacKay had a secret on Friday. 

She invited about 28 of her friends to donate $10 or more to the Red Cross for Ukrainian relief, and in exchange she would provide them with a surprise journey. 

MacKay, who used to organize worldwide trips as a career, offered few hints, but the flyer she used to sign up her Longboat Key tennis pals featured photos of an Egyptian pyramid and a dog sled. 

As her friends arrived on Friday afternoon at Cedars East chatted about their theories. A scavenger hunt? An escape room trip? Bar hopping?

Then, down Companion Way, came the unmistakable sounds of French horn-heavy, high-seas nautical music. And, a pirate ship built on a truck chassis. The Anna Maria Privateers had arrived, though the crew had to use all their seamanship (and seawomanship) to navigate the circle in front of Cedars East's clubhouse. 

"I just love giving back,'' MacKay, of Ukrainian descent, said. After loading up the provisions, the vessel set sail, er, drove off toward Anna Maria for a voyage of laughter and good times. 

 

Karen MacKay prepares to board with Jamie VanDenson and Kim Boyd, already on board.
Karen MacKay prepares to board with Jamie VanDenson and Kim Boyd, already on board.
Karen MacKay prepares to board with Jamie VanDenson and Kim Boyd, already on board.
Karen MacKay prepares to board with Jamie VanDenson and Kim Boyd, already on board.
The Anna Maria Privateers ship.
The Anna Maria Privateers ship.
Karen MacKay surprises her friends with a nautical day.
Karen MacKay surprises her friends with a nautical day.
Karen MacKay surprises her friends with a nautical day.
Karen MacKay surprises her friends with a nautical day.
Karen MacKay and her friends prepare to embark.
Karen MacKay and her friends prepare to embark.
Everyone gets ready to board.
Everyone gets ready to board.
Everyone gets ready to board.
Everyone gets ready to board.
Karen MacKay prepares to board with Jamie VanDenson and Kim Boyd, already on board.
Karen MacKay prepares to board with Jamie VanDenson and Kim Boyd, already on board.

 

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