• Alternate Text
  • Loading

  • Sand Bucket List
  • Health Observed
  • Crossword
  • Contests
  • Newsletters
  • e-Newspaper App
  • Longboat
    • News
    • Cops Corner
    • Real Estate
    • Business
    • Neighbors
    • Opinion
  • East County
    • News
    • Real Estate
    • Business
    • Neighbors
    • Schools
    • Sports
    • Opinion
  • Sarasota
    • News
    • Cops Corner
    • Real Estate
    • Business
    • Neighbors
    • Schools
    • Sports
    • Opinion
    • Siesta Key
  • Arts + Entertainment
    • Eat + Drink
    • Arts + Culture
    • Reviews
    • Things To Do
    • Black Tie
    • Spotlight Partners
  • Things to Do
  • Galleries
  • More
    • Hurricane Season
    • Elections
    • Health Observed
    • Sand Bucket List
    • Calendar
    • Celebrations
    • Contests
    • Tributes
    • Submit a Celebration
    • Submit a Tribute
    • Public Notices
    • Classifieds
  • Longboat
    • Longboat
    • News
    • Cops Corner
    • Real Estate
    • Business
    • Neighbors
    • Opinion
  • East County
    • East County
    • News
    • Real Estate
    • Business
    • Neighbors
    • Schools
    • Sports
    • Opinion
  • Sarasota
    • Sarasota
    • News
    • Cops Corner
    • Real Estate
    • Business
    • Neighbors
    • Schools
    • Sports
    • Opinion
    • Siesta Key
  • Arts + Entertainment
    • Arts + Entertainment
    • Eat + Drink
    • Arts + Culture
    • Reviews
    • Things To Do
    • Black Tie
    • Spotlight Partners
  • Things to Do
  • Galleries
  • More
    • More
    • Hurricane Season
    • Elections
    • Health Observed
    • Sand Bucket List
    • Calendar
    • Celebrations
    • Contests
    • Tributes
    • Submit a Celebration
    • Submit a Tribute
    • Public Notices
    • Classifieds
  • Sand Bucket List
  • Health Observed
  • Crossword
  • Contests
  • Newsletters
  • e-Newspaper App

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.

 

Latest News

St. Lucie County Administrator George Landry has been recommended by Howard Tipton to replace him as town manager as Tipton prepares to retire.
  • June 19, 2026
New town manager recommended for Longboat Key
Woman charged in three high-profile Sarasota burglaries
  • June 18, 2026
Woman charged in three high-profile Sarasota burglaries
The Florida Highway Patrol is investigating the crash.
  • June 18, 2026
Driver dies of injuries in blowout-triggered crash in Sarasota
Tony Barrett speaks at a candidate forum in April at the Lakewood Ranch Country Club.
  • June 18, 2026
Manatee County Commission candidate charged with domestic battery

Sponsored Health Content

Sponsored Content

The best of Your Observer, delivered directly to your inbox

Get the latest in news, sports, schools, arts and things to do in Sarasota, Siesta Key, Longboat Key and East County.

Sign Up

Latest in Neighbors

Attendees were impressed by the fireworks across Sarasota Bay.
  • June 19, 2026
Fourth of July 2026 events in Sarasota, Longboat Key and Lakewood Ranch
The town of Longboat Key has installed new signage at beach access points on the island.
  • June 18, 2026
Informational signs posted on Longboat beaches
Class participant Michael Hartman begins to put on the AED pads to the CPR mannequin.
  • June 18, 2026
Learn a life-saving skill this summer
Waves of red, white and blue flooded Bay Isles Road for the 2024 Freedom Fest parade. While the patriotic display was impressive, organizers of the upcoming Fourth of July festivities believe the activities planned for this special 250th edition will be bigger and better than ever.
  • June 17, 2026
Get ready for a special edition of Longboat's 'shortest parade in America'
Former Rotary Club of Longboat Key President Jan Wallace congratulates current President Terri Driver, who made club history in accepting the role two years in a row at the June 11 cerermony.
  • June 15, 2026
Longboat Rotarians reflect on community impact at annual gathering
More than 40 residents attended Christ Church of Longboat Key's first summer lunch meetup at Pork Belly's Eatery & Catering Co., a new high turnout for the event.
  • June 15, 2026
Longboaters catch up while supporting local eateries

App

Download the Your Observer app

Stay in the know with the latest local news. Any device, anytime, anywhere.

DOWNLOAD NOW

Contact

  • 1970 Main St.
  • Third Floor
  • Sarasota, FL 34236
  • Phone: 941-366-3468
  • FPN Verified

Extra, Extra!

  • Newsletters
  • App
  • Crossword
  • Contests

more

  • About Us
  • Contact Us
  • Classifieds
  • Advertise
  • Rack Locations
  • Jobs
  • Privacy Policy
  • Accessibility Options

sister sites

  • Business Observer
  • Jax Daily Record
  • Orange Observer
  • Accessibility Options
  • Copyright © 2026 Observer Media Group Inc., All Rights Reserved
Sign Up for Daily Headlines

A daily dose of news from Longboat Key, East County, Sarasota and Siesta Key.

Sign Up for In Case You Missed It

A Saturday dose of the week's top stories from Sarasota, Longboat Key and East County.


Anytime. Anywhere. Observer.

From in-depth local reporting to real-time breaking news, stay connected to the stories shaping our community with the Your Observer app.

Download Now for Free