Thursday, November 13, 2025 / by Mike Shoaff
Naples Holiday Highlights: Celebrate the Season in Style
Celebrate the 2025 to 2026 Season in Style: Naples Holiday Events Guide
As a dedicated realtor in Naples, Florida, I have seen how the community comes alive during the holiday season. From the sparkling lights on Fifth Avenue to the magical boat parades on Naples Bay, there is no better place to enjoy the holidays. Whether you are a longtime resident, a snowbird escaping the northern cold, or thinking about calling Naples home, this guide highlights the top holiday events for the 2025 to 2026 season.
If you are searching for Naples Christmas events 2025 or holiday activities in Naples FL 2026, this guide includes parades, concerts, festivals, and light displays that appeal to families, visitors, and locals alike.
November 2025: Start of the Holiday Magic in Naples
November kicks off the season with events that blend community, tradition, and festive decor. These early celebrations highlight Naples walkable downtown areas and vibrant culture.
Naples Festival of Trees
- Dates: November 18 to December 21, 2025
- Location: 701 5th Ave S. The Naples Players
Enjoy beautifully decorated trees. Free and open to the public. A great stop if you are exploring downtown properties.
Christmas on Third and Tree Lighting on Third Street
- Date: Thursday, November 24, 2025
- Time: Tree lighting 6:20 PM; snowfall and performances 8:00 PM
- Location: Third Street South
See Santa, enjoy carolers, and stroll through nightly snowfall through December 31. A perfect way to get a feel for downtown Naples homes and condos.
December 2025: Naples at Its Festive Best
December is the heart of the season. These Naples Christmas events draw thousands and highlight why people love living or investing here.
Fifth Avenue South Christmas Walk and Tree Lighting
- Dates: Friday December 5 and Saturday December 6, 2025
- Location: Fifth Avenue South
Experience tree lighting on Friday at 6 PM, entertainment, dining, and shopping. Fifth Avenue is known for its luxury lifestyle and popular residential options.
City of Naples Christmas Parade
- Date: Tuesday December 9, 2025
- Time: 6:30 PM
- Route: Third Street South to Fifth Avenue South to City Hall
A Naples tradition with floats, music, and lights. Great for discovering the charm of central Naples neighborhoods.
Christmas Boat Parade on Naples Bay- Date: Saturday December 13, 2025
- Time: 6:15 PM to 8:30 PM
- Location: Naples Bay
One of Naples most loved events. Arrive early for a waterfront view and explore bayfront real estate nearby.
Candlelight Christmas Carols- Date: Friday December 19, 2025
- Location: Cambier Park
Holiday Pops with the Naples Philharmonic
- Dates: December 18 to 21, 2025
- Location: Hayes Hall, Artis Naples
Dave Koz and Friends Christmas Tour
Date: December 1, 2025
- Time: 7:30 PM
- Location: Hayes Hall
A high energy holiday jazz performance.
Magic of Lights at Paradise Coast Sports Complex
- Dates: Late November 2025 through early January 2026
- Times: 6 PM to 9 PM weekdays, 6 PM to 10 PM weekends
Christmas at Palm Cottage
- Dates: December 2 to 24, 2025
- Times: Daytime tours Tue to Sat, free evenings Thu to Sat
Tour Naples oldest historic home decorated for the season.
Holiday Neighborhood Light Displays in Naples
Some neighborhoods are known for their incredible lights. These popular spots attract families and make for perfect evening drives.
- Victoria Park: A Naples tradition with themed displays.
- Golden Gate Estates: Star Grass Lane and surrounding streets shine bright.
- Palm River: North Naples charm with family friendly displays.
- Pelican Bay: Elegant lighting along Pelican Bay Boulevard.
- Port Royal: Luxurious waterfront homes lit for the holidays.
- Willoughby Acres: Nearly every home participates.
More details will be announced as December 25th approaches.
January 2026: Celebrate the New Year in Naples
The new year brings art fairs, concerts, shows, and community events.
Naples New Years Art Fair
- Dates: January 3 to 4, 2026
- Location: Cambier Park
A juried event featuring local and national art.
Naples Philharmonic Masterworks: New World Symphony
- Dates: January 8 to 9, 2026
- Location: Hayes Hall
Experience world class classical music.
Naples Art Show
- Dates: January 17 to 18, 2026
- Location: Fleischmann Park
A top event for fine art enthusiasts.
Naples Boat Show
- Dates: January 22 to 25, 2026
- Location: Sugden Park and Naples City Dock
The largest premier recreational show in the area.
Naples Winter Wine Festival
- Dates: January 30 to February 1, 2026
A world renowned wine and charity event supporting local children.
Plan Your Holiday Season in Naples Florida
From parades to concerts to neighborhood lights, Naples offers the perfect blend of sunshine, community spirit, and festive charm. If you are visiting or thinking about relocating, exploring the city during the holidays is a great way to experience the Naples lifestyle.
If you want help exploring neighborhoods or are considering buying or selling, I am always available to assist.
The holiday season is a great time to explore Naples and see our neighborhoods at their most festive. If you are thinking about making a move, downsizing, or purchasing a seasonal home, I can guide you through every step. With years of experience across Naples and areas from Gulf Shore to Lely Resort, I can help you make informed decisions and find the perfect fit. I invite you to reach out for a private holiday consultation. Call or text 239-298-9903 | www.NaplesHomeSearcher.com
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