There is a particular kind of magic to the holidays in Southwest Florida. The air is warm, the Gulf is calm, and somehow there is still snow falling on Third Street South. Our family has been part of this community for three generations, and the season still feels new to us every year.

Whether you live here full time, spend winters here, or are thinking about making Naples home, here is our local guide to the 2026 holiday season, from Thanksgiving weekend to New Year's.

A quick note: event details change, and some dates below are still being finalized by organizers. We have flagged anything you should confirm before heading out.

Kick Off the Season in Old Naples

Tree Lighting and Snowfall on Third Street South

Christmas on Third turns 49 this year, and it begins with the Naples Tree Lighting on Monday, November 23, from 6 to 9 p.m. The street closes to traffic, Santa arrives, and the lights come on with a snowfall to match. Through Thanksgiving week and into December, the district keeps up its evening snowfall at 7 p.m. on a set schedule, with live music most nights. Check Third Street South's website for the full calendar.

Families with little ones will love the new "North Pole Delivery District" tradition. Kids can pick up a Letter to Santa at participating shops and drop it in one of Santa's two mailboxes on the street.

The 5th Avenue South Christmas Walk

Just down the way, Fifth Avenue South holds its Christmas Walk and Tree Lighting on Friday, December 4, and Saturday, December 5, with the tree lighting in Sugden Plaza around 6 p.m. on Friday. Expect a living nativity, live music, Santa, and dinner on the Avenue. Reserve your table directly with your restaurant of choice, because these evenings fill up fast.

The City of Naples Christmas Parade

A local blog lists the City of Naples Christmas Parade for Tuesday, December 8, running from Third Street South onto Fifth Avenue South. Confirm the date and time with the City of Naples before you go.

Lights, Water, and Gardens

Night Lights at Naples Botanical Garden

If we could recommend just one evening out, this would be it. Johnsonville Night Lights in the Garden runs November 27, 2026, through January 3, 2027, and the Garden is dark on December 24, 25, and 31. Evenings often sell out, so book ahead. Standard ticket prices step up on December 18, so earlier in the season is easier on the wallet. Later entry times (7:45 p.m. or after) are also priced lower.

The Christmas Boat Parades

Naples Bay's Christmas Boat Parade, presented by the Marine Industries Association, is a long-running favorite, with viewing at the Naples City Dock and along the waterfront. Listings we found conflict on the date (some say Saturday, December 12, others December 19), so please confirm with the City of Naples or the Marine Industries Association before planning your evening. If you would rather watch from the water, several local charter companies offer parade cruises.

Over on Marco Island, the Christmas Island Style lighted boat parade is listed for Saturday, December 19, and the community's holiday street parade down San Marco Road is listed for Saturday, December 12. The Marco Island tree lighting and community celebration is listed for Saturday, December 5. Confirm details at Christmas Island Style.

Victoria Park Light Extravaganza

Tour through one of the most festive communities in Naples. Take a drive or ride your bike through Victoria Park and look at the amazing personal light displays of some really creative homeowners.