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December 2025
Bayshore Holiday Festival and Tree Lighting
We’re so excited to officially kick off the holiday season with the Annual Bayshore District Holiday Tree Lighting Festival on Thursday, December 4th at 5:30 PM This year’s celebration is our biggest yet, with district-wide activities including the tree lighting ceremony, caroling, holiday market, live music, outdoor movie, photos with Santa & Mrs. Claus, the Holiday Bayshore Walk, restaurant specials, and more. Your support truly makes a difference. If you could take a moment to share the event on your…
Find out more »Holiday Toy Drive
Friday, December 12 Holiday Toy Drive 12PM - 4PM Enjoy live music and complimentary beverages. The Guadalupe Center will be collecting donations for their Annual Toy Drive. Please consider giving the gift of a toy to make a wish come true for a young child this holiday season. Waterside Shops is proud to support the Guadalupe Center by donating 10% of sales, up to $25,000. Media Sponsor - Naples Illustrated
Find out more »February 2026
Wine Women and Shoes
Join us for an unforgettable afternoon of fashion, philanthropy, and fun at the highly anticipated Wine Women & Shoes event, all in support of Naples Cancer Advisors. Taking place on February 21, 2026, this signature celebration brings together Southwest Florida’s most stylish women and generous hearts to raise critical funds for local cancer support and advocacy. Enjoy world-class wine tastings, a glamorous fashion show, curated boutique shopping, and the ever-popular “Shoe Guys” experience — all set in an elegant atmosphere…
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