Schooner Woodwind was built to make sailing dreams come true back in 1993 by the Kaye family. For the past 30 plus years, guests from all over the world have sailed on her for public cruises, private events, multi-day cruises and educational cruises. Just 5 years later her sister, Woodwind II, set sail. Woodwind II is the “movie star” of the family – she played an important role in the movie Wedding Crashers. But it’s the classic Woodwind that sails every year in the Great Chesapeake Bay Schooner Race – and she’s known to be a fast competitor!

This year Woodwind is sailing on behalf of GCBSR's Education Fund. Contributions to the Woodwind team will be used to facilitate shipboard educational programming. Over the past three years, Woodwind has used funds raised in the Virtual Race to take kids and families from the Annapolis community out sailing. Many of these kids and families would not typically have easy access to this experience. While on the water, young sailors will raise the sails, steer the boat, and go through educational stations while learning about the nature in the Bay, sailing, and knot tying. The sails are a partnership between The Great Chesapeake Bay Schooner Race, the Schooner Woodwind, and a variety of local community programs.

This year, the Seafarer's Foundation was the recipient of a sailing cruise on the Woodwind for 30 students plus some chaperones. "The smiles on their faces when they get to sail together is so great. They love to sail the boat and learn more about the schooner," said Captain Jen. "We hope we can raise enough money to take them out again in 2025 and to also get other students on board the Woodwinds."

Welcome to the 2024 Virtual Great Chesapeake Bay Schooner Race!

While normal sailboat racing happens on the water, this race is completely online. Each participating schooner has teamed up with a nonprofit partner, and is racing to raise as much money as possible for their charity. YOU can participate in the race by choosing a schooner, making a contribution, and sharing this webpage with your family and friends! 90% of gifts will go directly to the charity of your choice. The other 10% will help the Great Chesapeake Bay Schooner Race achieve its mission to promote awareness of the Chesapeake Bay’s heritage; to encourage preservation of the Bay’s resources; to support Chesapeake Bay education and clean-up efforts; to bring historic schooners to the Bay; and to encourage schooner sailing and preservation. 

Please take a moment to learn more about our schooners and the organizations they support. At the start of the race, please come back here to make a donation and support your team!

Donation links will be available from 12:00 noon on Wednesday, August 21 through 3:00 PM on Saturday, August 24. 

Thank you for supporting our schooner community!

Please note:  GCBSR will only share your contact information with the charity you donated to.