Upper Keys Businesses and Residents Celebrated at Awards Gala
More than 250 people attended The Keys Weekly Best of Upper Keys awards at Playa Largo Resort on November 14, 2025, where restaurants, nonprofits, businesses and local personalities were honored. The event highlighted neighborhood pride and offered marketing and visibility boosts for winners, an outcome that matters for Monroe County small businesses and the tourism economy.
The Keys Weekly Best of Upper Keys awards drew more than 250 attendees to Playa Largo Resort on November 14, 2025, celebrating restaurants, businesses, nonprofits and civic figures across the Upper Keys. Organizers presented plaques and staged roasts to recognize local entrepreneurs and volunteers, underscoring the role of hospitality and community organizations in Monroe County’s economy.
Top winners included Square Grouper Islamorada, which took Best Overall Restaurant and Best Lunch. Florida Keys Brewing Co. emerged as a multiple category winner with Best Live Music, Best Bar and Best Beer Selection. In Key Largo, C and C Wood Fired Eats received Best Happy Hour and Best Pizza, while Robbie’s Hungry Tarpon won Best Bloody Mary. Community and civic honors went to Plantation Key Colony for Best Neighborhood and Monroe County Commissioner Holly Raschein for Best Elected Official. The full winners list was published on Keys Weekly on November 20, 2025.
For local businesses the practical impact of such awards can be immediate. Recognition in regional media often translates into increased visibility for out of area visitors as well as for residents deciding where to dine and shop. In tourism driven economies like the Florida Keys, reputation signals from community awards can nudge consumer choice during peak seasons and slow periods alike, helping small establishments sustain demand and justify modest marketing investments.
The ceremony also served as a networking moment for business owners and civic leaders. Community recognition events consolidate goodwill, spotlight volunteer efforts and provide officials with touch points to hear business concerns. Commissioner Holly Raschein’s recognition underscores the intersection of elected leadership and the business climate, an intersection that influences permitting, infrastructure priorities and promotional partnerships that affect long term growth.
While awards do not substitute for strategic investments in workforce, supply chains and resilience planning, they contribute to branding that supports visitor spending, which is central to the Monroe County economy. Plaques and social media posts that follow an awards season can extend the return on one night’s publicity into months of increased bookings and foot traffic.
The Best of Upper Keys ceremony also highlighted the variety of neighborhood level assets, from Plantation Key Colony to family run eateries, signaling to residents and policymakers alike that economic vitality is distributed across small scale operators. Readers interested in the complete list of winners can find it on Keys Weekly’s website, where the paper published the full results on November 20, 2025.
