Old Naples Lights Its Christmas Trees Eleven Days Apart, and Each Street Asks for a Different Kind of Evening

Third Street South names its event the Naples Tree Lighting and holds it Monday, November 23, from 6 to 9 p.m. Fifth Avenue South calls its event the official Christmas tree lighting and holds it in Sugden Plaza at about 6 p.m. on Friday, December 4.

The eleven days between them mark two different ways of running a holiday season. Third Street South spreads its season over five weeks on a fixed schedule, so nearly any December Thursday will do. Fifth Avenue South packs most of its season into two days, and the most sought-after part of those two days runs through restaurant reservations. On Third Street, the planning question is which night to go. On Fifth Avenue, it is which table, and that one has a deadline.

Third Street Goes First, Then Keeps Going

The 49th annual Christmas on Third starts the Monday of Thanksgiving week. Third Street South closes to traffic for the tree lighting that evening. The tree goes up in one night. Everything after it follows a pattern.

Thanksgiving week, November 24 through 28

From Tuesday through Saturday the district runs the same evening on each programmed night:

• Live music from 5 to 8 p.m.
• Snowfall at 7 p.m.
• Shops open until 7 p.m.
• No programming on Thanksgiving Day, Thursday, November 26

So the week has four evenings of programming. Wednesday and Friday sit on either side of the holiday, and Saturday closes the week.

December, Thursday through Saturday

In December the schedule narrows to the end of the week. Christmas music plays 5 to 8 p.m. on Thursdays and Fridays, snow falls at 7 p.m. on Thursdays, Fridays and Saturdays, and shops stay open until 7. Christmas Day, a Friday this year, has no programming.

That gives Third Street a snowfall on most weekend-adjacent nights of the month. If one Thursday falls through, the same program comes back the next week, and no reservation is involved.

The two dates that do not repeat

Two Third Street events fall outside the weekly pattern. Letters to Santa are available at participating shops from November 25 through December 23. Children drop them in one of two mailboxes, at Fleischmann Plaza near Gattle's or at Santa's Workshop near Sea Salt, after the district was named a North Pole Delivery District. One child is picked for a surprise delivery.

Santa Paws returns Saturday, December 12, from 1 to 3 p.m. Leashed pets can have photos with Santa and Mrs. Claus near Sea Salt, and the PawTographers will be on-site. That Saturday is also a snowfall night, so pet photos in the afternoon and snow at 7 p.m. fit on one calendar day.

Fifth Avenue Saves It All for One Weekend

The Fifth Avenue South Christmas Walk runs Friday, December 4, from 5 to 10 p.m., and Saturday, December 5, from 10 a.m. to 10 p.m. The Sugden Plaza tree lighting, a living nativity, a skating rink, live music and Santa all fall inside that window, and the district calls the two-day festival the biggest Christmas showcase in Naples. A day-long Christmas Market is also listed, with details marked as coming soon on the district's page.

Third Street's evenings are walk-up. The center of the Fifth Avenue weekend is what the district calls dinners on the Avenue. Participating restaurants serve dinners during the festivities, and every reservation goes directly through the individual restaurant. No central booking line exists. There are as many reservation books as there are restaurants, each filling at its own pace for the same two nights.

The restaurants on the list

The district's 2026 list of participating restaurants:

That makes 23 restaurants in all. Two of them have changed since last December, and a third has new menus for the holidays.

Two names that are new to the weekend

Medi is the newest entry. The Fifth Avenue South district announced that Vergina, one of downtown's longest-standing restaurants, would start a new chapter as Medi, a Mediterranean restaurant and entertainment venue inspired by St. Tropez, with a debut date of October 26. So a familiar address arrives at its first Christmas Walk under a new name and a new format.

Pazzo! Cucina Italiana closed temporarily for roof and kitchen improvements and announced a reopening for Tuesday, October 27, in time for its 31st anniversary. The announcement mentioned an updated Italian menu, longtime favorites, and plans to offer lunch for the first time in the restaurant's history. Pazzo is on the district's list of restaurants serving dinners during the Walk.

Le Colonial, the French-Vietnamese restaurant on the list, launched new private dining and catering menus in October for holiday parties and corporate gatherings. The district also flagged its first Thanksgiving, with a Vietnamese take on the holiday meal. That makes it one of the few Fifth Avenue tables with a holiday connection before the Walk weekend.

The Avenue Under the Lights Has Moved Around

The Christmas Walk is also a shopping walk, and several storefronts along the route have changed since last year's lights. Naples Press reported a round of moves among longtime Fifth Avenue businesses:

• Regatta has moved from 760 Fifth Ave. S. to 8799 U.S. 41 N.
• Aldo Castillo's gallery has moved from 634 Fifth Ave. S. to 472 Fifth Ave. S.
• East-West Sports Cards & Collectibles is moving from 785 Fifth Ave. into the former Castillo gallery space.
• Wind in the Willows now uses a side-street entrance in its building at 675 Fifth Ave. S., and Faherty has taken its former corner storefront.

Close to the west end of the avenue, Omasava is a reservation-only, chef-led omakase at 301 Fifth Ave. S. from the team behind Sails and Butcher Private, as Gulfshore Business reported. Its own site lists seatings at 5:30 and 8 p.m., about two and a half hours each, at $298 per guest before beverages, tax and service. Omasava is not one of the Christmas Walk restaurants. Its fixed seatings work like a booked table, the same as dinner on the Avenue.

The Walk Weekend Belongs to Both Streets

The two calendars overlap on both nights of the Walk. On Friday, December 4, Fifth Avenue lights its tree in Sugden Plaza at about 6 p.m., and Third Street's December Friday program runs at the same time, with Christmas music from 5 to 8 p.m. and snowfall at 7. On Saturday, December 5, Third Street's 7 p.m. snowfall happens during Fifth Avenue's full-day program.

That weekend brings the heaviest parking demand downtown, so the district's parking and transit guidance matters most then. It lists on-street parking, garages at 8th Street South and 6th Avenue and at 8th Street South and 4th Avenue, and a public lot at Park Street and 6th Avenue South. The Naples Trolley's usual hours are 8:30 a.m. to 5:30 p.m. On regular hours, the trolley stops half an hour after Friday's Walk starts.

Put together, the season comes down to a few dates:

1. Monday, November 23. Naples Tree Lighting on Third Street South, 6 to 9 p.m., with the street closed to traffic.
2. November 24 through 28, except Thanksgiving. Third Street music at 5 p.m. and snowfall at 7.
3. Before December 4. Fifth Avenue dinner reservations, each booked directly with the restaurant.
4. December 4 and 5. The Fifth Avenue Christmas Walk, with the Sugden Plaza lighting around 6 p.m. Friday and Third Street snowfall at 7 both nights.
5. Saturday, December 12. Santa Paws on Third Street, 1 to 3 p.m., then snowfall at 7.
6. Through December 23. Letters to Santa in the Fleischmann Plaza and Sea Salt mailboxes.

For Third Street, a free Thursday or Saturday at 7 p.m. is enough. For Fifth Avenue, the date is fixed and the only open question is whether your restaurant still has a table when you call.

If downtown's holiday calendar is part of why Old Naples appeals to you, or you're thinking about a home within walking distance of both trees, the Rigsby Team can show you the streets of Old Naples the way they are this season. Request a Private Consultation, and we'll plan your visit around the lights.