This is a unique and collaborative fundraiser by World Ocean School (WOS) and Alexandria Seaport Foundation (Seaport) to cover the costs for up to 10 current and graduate Apprentices to sail in the 2026 Great Chesapeake Bay Schooner Race aboard the Schooner Denis Sullivan and Pride of Baltimore II for an educational trip of a lifetime.

Schooner Denis Sullivan: is a three-masted wooden gaff rigged schooner originally from Milwaukee. The only existing replica of a 19th century Great Lakes schooner, she was envisioned and built by a Milwaukee-based team of professionals and volunteers.

World Ocean School: We empower students from all backgrounds to be courageous and compassionate changemakers for themselves, their communities, and our planet through transformative education aboard our iconic tall ships. World Ocean School provides immersive, hands-on education to more than 600 students from diverse backgrounds each year. Since its founding in 2002, more than 23,000 students have participated. 

Alexandria Seaport Foundation: The Apprentice Program is designed for young adults aged 18-23 who are eager to find a new path. Seaport uses the crafts of woodworking and traditional boatbuilding to teach job skills and positive habits that apprentices need for success in their work and personal life. Apprentices work alongside carpenters, boat builders, and volunteer mentors who teach and challenge them each day.

The young people Seaport serves need support to create a good life. Many have had issues with law enforcement, some have not succeeded in school, and many may suffer from anxiety or depression. The Apprentices need a nurturing environment to learn, grow, gain confidence, and build a path toward self-sufficiency and success.  Seaport’s curriculum, adult mentoring, community support, and career exploration give our Apprentices the positive environment they need.

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.