Charter fishing trip raises funds for Florida Keys Children’s Shelter

For Monroe County children who need a safe bed, counseling and a steady meal, one donated day on the water became direct support. A full-day charter aboard Miss Penny, sold through the Best of the Upper Keys 2025 silent auction, sent every dollar from the outing to the Florida Keys Children’s Shelter.

Richard Weinstein, Anton, Seth and Barry joined the trip, and the crew hauled in black grouper. The catch gave the outing a classic Keys feel, but the larger point was financial: a familiar charter-boat experience was turned into money for a local nonprofit that serves vulnerable youth and families.

The Florida Keys Children’s Shelter says it has provided residential and non-residential services since 1985 and is the only licensed emergency shelter for youth in Monroe County. Its services are offered at no charge and include shelter, food, counseling and other support for abused, abandoned, neglected, runaway, truant and ungovernable youth. A public listing describes a 19-bed Upper Keys facility in Tavernier and two group homes in Key West, serving youth from birth through age 18.

The donation also fit into a broader fundraising structure that has become important for the shelter. Since the inaugural Best of Keys in 2022, proceeds from Best of Upper Keys events have raised more than $70,000 for the organization, according to Keys Weekly. The 2025 cycle opened with nominations on Sept. 18, finalist voting began Oct. 16, and the fourth annual awards night was held Nov. 14, 2025, at Playa Largo Resort in Key Largo.

That mix of local business participation, outdoor recreation and nonprofit need has helped make the shelter’s fundraising unusually community-driven. Rather than relying only on formal appeals, the effort has used one of the Keys’ signature traditions, charter fishing, to generate support for children who need stability, case management and crisis services.

For the Miss Penny crew and the bidders who backed the trip, the result was simple: a day fishing in the Florida Keys became a practical contribution to a Monroe County institution that has been helping children and families for four decades.