Frequently Asked Questions

Do I have to participate in the Parade of Sail?

Parade participation is optional, but encouraged, as it helps develop public awareness of the event, is good for race publicity and helps generate future financial support. If you have room on board for a guest or two, please consider embarking some race sponsors or volunteers.

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.

Can I invite my family and friends to the land events?

The public may watch the Parade of Sail and view the schooners dockside in both ports. Other events are open only to captains, crew, sponsors and volunteers. (although some crew have been known to drive from one end of the Race to the other!

Why do I pay extra for my paying passengers?

Race expenses grow in direct proportion to the number of people on board participating schooners. We expect commercial vessels to pass some of this cost on to their customers.

Why do you request a donation from participants?

Fundamentally, this is a fundraiser. We are raising funds for non-profit organizations around the Bay area that support our mission of promoting education and public awareness of the Chesapeake Bay’s maritime heritage and encouraging the preservation and improvement of the Chesapeake’s natural resources. We keep the registration costs to the bare minimum, in fact they barely cover the cost of putting on the race, so as to encourage registration from all possible schooners and their captains. Many captains, even those not participating, enjoy making a contribution to assure the continued success of this event and support its mission. Some schooners have even held private fundraisers to support the GCBSR. We want the event to be affordable for all schooners so donations are strictly voluntary but highly encouraged. Donations to the race are tax deductible under 501(c)3 and qualify for employer matches. We list each donation under the boat’s name on our promotional materials unless you instruct otherwise.

Net 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, donees have included the Chesapeake Bay Foundation, Sail Baltimore, Oyster Recovery Project, Elizabeth River Project and the Mariners Museum in Yorktown, among others. If you have a needy organization in mind, we’d love to hear your suggestion! Please contact

What if my plans change after I send the entry forms?

Please let us know. Send a message to

Is my entry fee refundable?

No. Your entry fee is not refundable. This race is a fundraiser for charitable giving, so your money will go to good use.

Why do you want so much information about my schooner?

We like to know about all of the schooners for publicity purposes. We’d like to know how long you’ve had her, where you have been sailing her, what you know about her history, and anything about her that makes you love her. Please email photos to

What should I tell the cook?

We will assist with transportation for provisioning in both ports. Sixteen pound bags of ice will be available in Norfolk. We feed you and your crew on Wednesday night, Saturday afternoon and Sunday morning. Other meals are on your own. There are great places to eat within an easy walk of our docks in both ports.