Frequently Asked Questions

Answers to many of the questions we get from the public. Captains – Do you have a question? See our Captain’s FAQ for answers.

What is the purpose of this event?

The mission of the Great Chesapeake Bay Schooner Race (GCBSR) is to promote public awareness of the Chesapeake Bay’s maritime heritage and encourage the preservation and improvement of the Chesapeake’s natural resources.

Who benefits from this year's race?

Proceeds from the Great Chesapeake Bay Schooner Race support local non-profits in the two areas where we celebrate the race, Baltimore/Annapolis and Portsmouth/Norfolk. Local organizations are sought out whose mission aligns with ours. To date, we have donated to the Chesapeake Bay Foundation, Sail Baltimore, Oyster Recovery Project, Elizabeth River Project and the Mariners Museum in Yorktown. If you have a needy organization in mind, we’d love to hear your suggestion! Please contact Nan Nawrocki ( Thanks!

How big is the event?

In 2017, there were 31 entries. One year 54 boats signed up to compete. More than 150 schooners have participated over the last twenty-five years.

How did it start?

The first annual race was in 1990, with seven entries. Every one of those seven has returned; Norfolk Rebel has raced every year. Forty schooners have raced five or more times.

Who can participate?

Entry is open to all schooner-rigged vessels. The race committee reserves the right to reject entries for reasons of safety.

Can my friend's classic wooden ketch sail in company?

Sorry, only schooners, no spectator fleet.

I may not race until next year; how can I check it out?

Owners and captains of nonparticipating schooners are invited to contact us to arrange admission to land events.

What if I can't get away for the whole event?

If your schedule will not permit participation in all events, we still want you to come. Contact us to make arrangements.

Who organizes this race?

The Great Chesapeake Bay Schooner Race, Inc. is a Virginia nonprofit corporation under IRS 501(c)(3). About 100 volunteers in each port, led by race chairs, make the race and activities run smoothly.