Courageous Sailing Awarded $150,000 Cummings Grant

Special to the patriot-Bridge

Courageous Sailing is thrilled and honored to be one of 150 local nonprofits chosen by the Cummings Foundation as part of their $30 million annual grants program. The Charlestown-based organization was selected from a total of 630 applicants during a competitive review process. It will receive $150,000 over three years.

Courageous Sailing, founded in 1987, supports its community through lessons and memberships for adults, sailing for those with special needs, corporate teambuilding, and youth development opportunities. Courageous is committed to ensuring equitable access to high-quality, engaging, multi-year summer and school-year learning opportunities for kids throughout Boston and beyond. “Sustained funding like this makes such a huge difference in our ability to provide free programming for Boston students who wouldn’t otherwise be able to participate,” said Executive Director Dave DiLorenzo. “The Cummings Foundation played a formative role in the development of Swim Sail Science and some of our most critical programs back in 2015-2016, and it means a lot that they’ve chosen to invest in Courageous’s future.” Courageous will use the grant to support and strengthen a variety of school-year and summer sailing, STEM, and academic programs serving youth from low-income communities.

The Cummings $30 Million Grant Program primarily supports Massachusetts nonprofits that are based in and serve Middlesex, Essex, and Suffolk counties.

Through this place-based initiative, Cummings Foundation aims to give back in the areas where it owns commercial property. Its buildings are all managed, at no cost to the Foundation, by its affiliate, Cummings Properties. This Woburn-based commercial real estate firm leases and manages 11 million square feet of debt-free space, the majority of which exclusively benefits the Foundation.

“The way the local nonprofit sector perseveres, steps up, and pivots to meet the shifting needs of the community is most impressive,” said Cummings Foundation executive director Joyce Vyriotes. “We are incredibly grateful for these tireless efforts to support people in the community and to increase equity and access to opportunities.”

The majority of the grant decisions were made by about 90 volunteers. They worked across a variety of committees to review and discuss the proposals and then, together, determine which requests would be funded. Among these community volunteers were business and nonprofit leaders, mayors, college presidents, and experts in areas such as finance and DEI (diversity, equity, and inclusion).

“It would not be possible for the Foundation to hire the diversity and depth of expertise and insights that our volunteers bring to the process,” said Vyriotes. “We so appreciate the substantial time and thought they dedicated toward ensuring that our democratized version of philanthropy results in equitable outcomes that will really move the needle on important issues in local communities.”

The Foundation and volunteers first identified 150 organizations to receive three-year grants of up to $225,000 each. The winners included first-time recipients as well as nonprofits that had previously received Cummings grants. Twenty-five of this latter group of repeat recipients were then selected by a volunteer panel to have their grants elevated to 10-year awards ranging from $300,000 to $1 million each.

This year’s grant recipients represent a wide variety of causes, including housing and food insecurity, workforce development, immigrant services, social justice, education, and mental health services. The nonprofits are spread across 46 different cities and towns.

Cummings Foundation has now awarded $480 million to greater Boston nonprofits. The complete list of this year’s 150 grant winners, plus nearly 1,500 previous recipients, is available at 

Since its inception in 1987, Courageous Sailing has been dedicated to their mission of transforming lives through sailing programs that inspire learning, personal growth, and leadership. Courageous was established by Boston sailing enthusiast Harry McDonough, who envisioned the sport of sailing as a means of fostering unity and life skills in children of all economic and ethnic backgrounds. Courageous is now a nationally recognized, year-round educational center, serving the community through lessons and memberships for adults, sailing for those with special needs, corporate teambuilding, and youth development opportunities. Courageous Sailing’s Reach Initiative engages marginalized Boston youth through high-quality, multi-year, summer and school-day programs that combine sailing, swimming, and academics to foster social-emotional and academic growth.

Woburn-based Cummings Foundation, Inc. was established in 1986 by Joyce and Bill Cummings of Winchester, MA and has grown to be one of the largest private foundations in New England. The Foundation directly operates its own charitable subsidiaries, including New Horizons retirement communities, in Marlborough and Woburn, and Cummings Health Sciences, LLC. Additional information is available at

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