The Adventuress Cup is both a real on-the-water race and a peer-to-peer fundraiser. Teams earn points through:
On-the-water race results
Fundraising (each dollar raised contributes points)
Pre-race challenges (Wind in Your Sails) and other activities
Fundraising and participation help directly support youth programs and the care of the schooner Adventuress.

For sailboats equipped with spinnakers:
Race in the main fleet with flying sails.
Fundraising goal: Recommended good-faith pledge of $1,500 (peer-to-peer or direct contributions).
Registration includes an event burgee and a t-shirt; additional shirts available.
(Skippers gather a crew and race under handicap rules.)

For sailboats without spinnakers:
Same format as above but without flying sails.
Fundraising goal: Recommended good-faith pledge of $1,500.
Registration includes an event burgee and a t-shirt; additional shirts available.

For powerboats that want to join the pre-race parade (not a race class):
Cruise past the Adventuress and race course area during the parade.
Fundraising goal: Recommended good-faith pledge of $1,500.
Includes exclusive burgee and t-shirt; t-shirt extras available.

For small one-design sailboats (e.g., Laser, Opti, FJ, Hobie, etc.):
Separate dinghy race course.
No minimum fundraising requirement, but you’re encouraged to set a personal fundraising goal and create a peer-to-peer page.
Includes an event t-shirt; additional shirts available.

Participate without a physical boat:
Create a “virtual boat” team and fundraise online.
No minimum fundraising requirement (optional fundraising page).

Support a friend’s racing or fundraising team:
Sign up to help with fundraising or team support.
Does not include a skipper packet; race t-shirts can be purchased.
Note: Only use this category if joining an existing team — teams must choose a primary racing category.
Even if you don’t bring a boat:
Join from shore — track the race and enjoy community festivities.
Fundraise or donate — support youth programs and the Adventuress.
Participate in Wind in Your Sails Challenges to earn extra points and engage in marine-related learning.