Olde Naples has two separate tree lightings this year. Third Street South goes first, on Monday, November 23. Fifth Avenue South lights its tree at Sugden Plaza eleven days later, on Friday, December 4. Four days after that, on Tuesday, December 8, the City of Naples Christmas Parade forms on Third Street South and travels up to Fifth Avenue South. Each event has its own organizer, schedule and street, and together they make up one downtown holiday season that you can walk in order.
| Date | Event | Where | Hours |
|---|---|---|---|
| Mon, Nov 23 | 49th Annual Christmas Tree Lighting | Third Street South | Evening, until 9 PM |
| Nov 24–28 | Thanksgiving-week music and snowfall | Third Street South | Music 5–8 PM, snow at 7 PM |
| Fri, Dec 4 | Christmas Walk and tree lighting | Fifth Avenue South, Sugden Plaza | 5–10 PM, lighting about 6 PM |
| Sat, Dec 5 | Christmas Walk, day two | Fifth Avenue South | 10 AM–10 PM |
| Tue, Dec 8 | City of Naples Christmas Parade | 3rd St S and 9th Ave S to City Hall | Starts 6:30 PM |
| Sat, Dec 12 | Santa Paws | Third Street South, near Sea Salt | 1–3 PM |
Third Street Opens the Season on a Monday
The 49th Annual Christmas Tree Lighting falls on Monday, November 23, which is the Monday before Thanksgiving. It held the same spot on the calendar last year, when the 48th lighting was on Monday, November 24, 2025. In both years, the lighting falls three days before Thanksgiving.
On the district's Christmas on Third page, the celebration runs from 6 to 9 PM, and Third Street South closes to traffic for the evening. According to the City's description, Santa arrives on a vintage fire truck, the official tree lighting follows, and the evening also has snowfall, local vendors and shops and restaurants that stay open late. The City's listing sends questions to Third Street South, so the district is the place to check on the day for any changes.
This lighting starts the season. It is also the first of several nights on Third Street South, which keeps a holiday schedule going from November 23 until Christmas.
The Week Between the Lighting and the Turkey
After the tree is lit, Third Street South keeps the street busy for the rest of Thanksgiving week. Live music runs Tuesday through Saturday from 5 to 8 PM, snow falls at 7 PM, and shops stay open until 7 PM. Thanksgiving Day itself has no programming. The district's listing for the week runs from the lighting on November 23 through November 29.
That makes the week easy to plan around family visits. If guests arrive Tuesday or Wednesday, they can still catch the 7 PM snowfall and live music on Third Street that same evening. On Friday and Saturday after the holiday, the same schedule repeats.
The district's new tradition starts on Wednesday, November 25. Third Street South calls itself a North Pole Delivery District this year. Children pick up an official Letter to Santa at participating shops, and the letters are available from November 25 through December 23. Finished letters go in one of two official mailboxes:
- Fleischmann Plaza, near Gattle's
- Santa's Workshop, near Sea Salt
The district says Santa's Elves will choose one child to receive a special surprise.
Fifth Avenue Lights Its Tree Eleven Days Later
The second lighting is the Christmas Walk on Fifth Avenue South, organized by the 5th Avenue South Business Improvement District. It runs Friday, December 4, from 5 to 10 PM and Saturday, December 5, from 10 AM to 10 PM. The tree lighting ceremony starts at about 6 PM Friday.
Like Third Street, Fifth Avenue moved its dates one calendar day earlier than in 2025, when the walk ran December 5 and 6. Each street kept its place in the season, and the eleven-day gap between the two lightings is the same as last year.
The two lightings are different kinds of events. Third Street's is one evening that opens a month of weekly programming. Fifth Avenue's is a two-day festival. The avenue's event listing calls it "the biggest Christmas showcase in Naples" and lists the lighting in Sugden Plaza, a living nativity, a skating rink, live music and Santa. The Saturday session runs twelve hours, so families with young children can go in daylight and skip the Friday crowd.
Dinner on the Avenue
The other draw is Avenue dining. Twenty-three restaurants are listed as serving dinners during the festivities: BhaBha, BICE, Bistro 821, Bonta Bakery, Caffe Milano, Casa Neri, Chops City Grill, DelMar, Keewaydin's, La Pescheria, La Trattoria, Le Colonial, Medi, Molto, Ocean Prime, Osteria Tulia, Ottimo on 5th, Pazzo, Sails, Side Bar, Slice Shop, The Vine Room and Tulia Italian Steaks.
All reservations must be made directly with the specific restaurant.
That line on the Fifth Avenue South Christmas page matters most for Friday night. The ceremony begins at about 6 PM, so a table booked before or after the lighting decides how the evening goes. There is no central booking system, and each restaurant handles its own reservations.
The avenue's general access page lists parking garages at 8th Street South and at 6th and 4th Avenues, plus a public lot at Park Street and 6th Avenue South. It gives the Naples Trolley's daily hours as 8:30 AM to 5:30 PM, which ends before the Friday lighting begins.
The Parade Connects the Two Streets
The City of Naples Christmas Parade comes four days after Fifth Avenue's lighting, on Tuesday, December 8, at 6:30 PM. The City's parade page promises floats, marching bands, holiday music, performers and Santa. The City publishes the route in three steps:
- The parade begins at the corner of 3rd Street South and 9th Avenue South, at the Third Street end of the neighborhood.
- It travels up to 5th Avenue South.
- It finishes on 8th Street South in front of City Hall.
Those are the same two streets that held the season's tree lightings. The parade starts in the district that lit the first tree and passes through the one that lit the second, so households along the route can watch from the corner where the parade forms or walk a few blocks toward the end at City Hall.
The parade is also open to entries. The City accepts the 2026 parade application by email at [email protected]. Entries with vehicles must include a copy of a valid driver's license for every driver and proof of insurance for every participating vehicle. A neighborhood group, club or business considering a float should look at those requirements well before the Tuesday step-off.
Third Street Keeps Going Through December
After the two lightings and the parade, the season goes back to Third Street South, which runs a weekly holiday schedule from December through Christmas:
- Thursdays and Fridays: live Christmas music, 5–8 PM
- Thursdays, Fridays and Saturdays: snowfall at 7 PM
- Shops: open until 7 PM
- Christmas Day: no programming
Because of this schedule, the two districts fill different roles. Fifth Avenue concentrates its holiday programming into one weekend. Third Street spreads its programming across three evenings a week for the whole month, so snowfall at 7 PM is available on almost any December weekend a visitor arrives.
Families with pets have one more date. Santa Paws returns to Third Street South on Saturday, December 12, from 1 to 3 PM. Leashed dogs and other "furry, feathered, or four-legged friends" can have photos taken with Santa and Mrs. Claus near Sea Salt, and The PawTographers will be on site. December 12 is the Saturday after the parade, and Letters to Santa for the mailboxes at Fleischmann Plaza and Santa's Workshop stay available through December 23.
Planning the Season on Foot
The six dates follow the order of the neighborhood's streets. Third Street South opens the season on November 23 and runs programming through Thanksgiving week. Fifth Avenue South lights its tree on December 4 and stays open late on December 5. On December 8, the parade forms at 3rd Street South and 9th Avenue South, travels up to Fifth and ends at City Hall. On December 12, Santa and Mrs. Claus are back near Sea Salt for pet photos, and weekly snowfall continues on Third until Christmas.
For a household with guests staying all season, these events cover four weekday evenings and a full Saturday without leaving Olde Naples. The dates to put on the calendar first are November 23 for the first tree, December 4 for the second, and December 8 at 6:30 PM for the parade from 3rd Street South and 9th Avenue South to City Hall.
If you're hosting family in Olde Naples this season, or thinking about which downtown street you'd like to live on before next year's lightings, Taranto Team knows these blocks well, including which corners are quiet and which are part of the parade route. Schedule a private consultation with Michael and Lauren, and we'll talk through the season and the streets with you.
