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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 »Swamp Heritage Festival
Taking place on December 6th, the 2025 Swamp Heritage Festival celebrates Big Cypress National Preserve while also highlighting the thousands of years of inhabitants that preceded and protected this area before it was formally set aside. This year, we hope to inspire visitors to see Big Cypress as a place where ‘Art Meets the Wild’. Through artistic talks, cultural demonstrations, thrilling stories, and hands-on activities, we will explore the ways in which people have found endless inspiration in the swamp.…
Find out more »Strolling Santa
Find Santa and snap a pic with him as he strolls Waterside Shops Saturdays, December 6th + 13th + 20th 12PM – 4PM
Find out more »LETTERS TO SANTA FREE WORKSHOP
FREE Christmas Workshop for Kids! ✨🎅 Join us for our very first Letters to Santa Workshop hosted by K Signature Events at Bad Ass Coffee of Naples ☕️🎄 📅 Sunday, December 7th 🕑 2:00 – 4:00 PM 📍 1307 3rd St S, Naples, FL 34102 Kids of all ages are invited to write their letters to Santa, make crafts, and enjoy a festive holiday afternoon — all while parents relax and sip their favorite coffee! ❤️ ✨ This is a…
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 »Strolling Santa
Find Santa and snap a pic with him as he strolls Waterside Shops Saturdays, December 6th + 13th + 20th 12PM – 4PM
Find out more »DR. SEUSS’ HOW THE GRINCH STOLE CHRISTMAS (2000): 25th Anniversary Movie Party at Alamo Drafthouse
Join us at Alamo Drafthouse Cinema in Naples for a Movie Party screening of DR. SEUSS’ HOW THE GRINCH STOLE CHRISTMAS (2000): 25th Anniversary on Dec. 14. Discover the true meaning of the holiday season with this live-action adaptation of the beloved classic. Why is the Grinch such a grouch? No one seems to know, until little Cindy Lou Who takes matters into her own hands and turns both Whoville and the Grinch's world upside down, inside out…and funny side…
Find out more »Fiesta Navideña – Latin Christmas Fiesta
Felipe's Taqueria will celebrate the holiday season with Fiesta Navideña – Latin Christmas Fiesta on Friday, Dec. 19, at its Logan Landings location, 2220 Logan Blvd. N., Suite 810. The festive event will feature live music, traditional Latin games and a special holiday menu showcasing traditional dishes from across Latin America. The Friday celebration at Logan Landings will kick into high gear with live music from the Black & White Band from 6 to 10 p.m., with speed rounds of…
Find out more »Strolling Santa
Find Santa and snap a pic with him as he strolls Waterside Shops Saturdays, December 6th + 13th + 20th 12PM – 4PM
Find out more »Disco Bean Coffee Company Ribbon-Cutting Ceremony
This retro-inspired concept blends specialty Colombian coffee, music culture, and late-night ambiance into one family-friendly destination. Its speakeasy-style atmosphere transports guests back in time while they enjoy freshly sourced coffee, tea, beer and wine, hand-scooped ice cream, donuts, grab and go sandwiches, and a full vinyl record shop featuring new artists, classics and rare finds. Disco Bean Coffee Company will be open Monday through Thursday from 8 a.m. to 8 p.m., Fridays and Saturdays from 8 a.m. to midnight, and…
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