Schooner Woodwind was built to make sailing dreams come true back in 1993 by the Kaye family. For the past 30+ years, guests from all over the world have sailed on her and her sistership, Woodwind II, for public cruises, private events, multi-day cruises and educational cruises. 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 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. The sails are a partnership between The Great Chesapeake Bay Schooner Race, the Schooner Woodwind, and the Seafarer's Youth Program. These programs give young people an opportunity to experience the fun of sailing and the excitement that comes with it, along with learning the science and camaraderie that sailing brings.

Welcome to the 2026 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 12 through 3:00 PM on Saturday, August 15. 

Thank you for supporting our schooner community!

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