Having come from a family of doctors, Willard was a strong believer in compassionate end-of-life care and the hospice movement. He was a determined advocate and active Spokesperson for The National Hospice Regatta Alliance, an association that facilitates a network of regional sailing regattas every year, and organizes a National Championship and Gala, all benefiting local nonprofit hospices. He loved being involved with the Alliance and cherished the friendships he developed.

Each year he authorized one of his racing images to be used for the Alliance's publicity and annual posters and awards. Willard's family continues the partnership, and makes one of Willard’s distinctive images of sailing and sailboat racing available to the organization each year, to support the hospice sailing regattas in raising funds for their local non-profit hospices. The locations of that year's participating hospice regattas are imprinted around the image borders.