Third Street Lights First: The Old Naples Holiday Season, Block by Block

When does the holiday season start in Old Naples? Downtown has two answers, and two separate organizations give them. The Third Street South Association lights its tree on Monday, November 23. The Fifth Avenue South Business Improvement District lights its tree 11 days later, on Friday, December 4.

Each calendar runs differently, and this year the first month belongs to the south end of the neighborhood. The winter farmers market, Thanksgiving week's snowfall, the Santa mailboxes and the only beach walkways open near the pier are all within a few blocks of Broad Avenue South and 13th Avenue South. Fifth Avenue's turn comes in December, and even then, part of the avenue is still behind construction fencing.

The Season, Date by Date

Before December 4, nearly everything on the list happens at Third Street South or Cambier Park.

It Starts on a Saturday Morning

The season really begins two days after this post publishes. The Third Street South Farmers Market opens its winter season on Saturday, November 7. It runs from 7:30 to 11:30 a.m. on Third Street South between Broad Avenue and 13th Avenue South, and it repeats at the same hours every Saturday after that.

The association says the market has no national chains or franchises. It connects local growers and independent agricultural merchants with local buyers, and the listing invites shoppers to bring friends, family and pets. The vendor roster on the market's page is still the summer list. It includes Inyoni Farms, Gulfcoast Greens, Mondragon Farms, Stamper Cheese, Neapolitan Bake Shop, Jimmy's Java and King of Conch Salads. The first few Saturdays will show how much of that summer lineup carries into winter.

The Beach Walk Moved South, Too

The market's two boundary streets matter for another reason this year. The Naples Pier is closed for its rebuild. According to the City of Naples project page, the closure covers the pier itself, its stairs, restrooms and showers, and 12th Avenue South west of Gulf Shore Boulevard South. Only the western third of the pier parking lot is open to the public. The other two-thirds are used for construction.

To keep the beach open, the city set up pedestrian bypasses at the Broad Avenue South and 13th Avenue South beach ends, with restrooms at both. Those are the same two streets that frame the farmers market. On a Saturday this winter, a coffee from the market and a walk to the water both happen within that one stretch of the grid.

The closure lasts all season. The city reports that contractor Shoreline Foundation Inc. drove the last of the 193 reinforced-concrete pilings on October 7, 2026. The mid-pavilion concrete pour on September 18 pushed the project past 50 percent of the concrete it needs. Structural work is expected to finish in early 2027. After that, crews will lay the ipe decking, and the pier is on schedule to reopen in July 2027. The holiday season and the season after it will both happen with the pier fenced off.

Thanksgiving Week Belongs to Third Street

The 49th annual Christmas on Third starts with the Naples Tree Lighting on Monday, November 23, from 6 to 9 p.m. Third Street South closes to traffic for the evening. The association's event listing gives 1207 3rd Street S. as the address.

The rest of the week has a set rhythm. From Tuesday through Saturday, live music runs from 5 to 8 p.m., the snowfall starts at 7 p.m., and shops stay open until 7 p.m. Nothing is scheduled on Thanksgiving Day itself. That leaves four evenings of snowfall when out-of-town family is most likely to be visiting.

Two newer additions run past Thanksgiving week:

• North Pole Delivery District. From November 25 to December 23, children can pick up a Letter to Santa at participating shops. They can mail it at Fleischmann Plaza near Gattle's or at Santa's Workshop near Sea Salt, and the elves will choose one child for a surprise delivery.
• Santa Paws. On Saturday, December 12, from 1 to 3 p.m., leashed pets can have photos taken with Santa and Mrs. Claus near Sea Salt, with the PawTographers on-site.

Cambier Park Fills the Weekends In Between

Cambier Park keeps a steady schedule between the two districts. It hosts an evening and an afternoon of big band music, two art shows and a December concert band afternoon, according to the Fifth Avenue South events calendar. The Fine Arts & Craft Show on November 14 and Art in the Park on November 28 are both daytime Saturday events. Art in the Park falls on the Saturday after Thanksgiving, the last night of Third Street's snowfall week.

The park's playground is changing more slowly. The city's recreation projects page says the replacement is in permitting and manufacturing. The final design is a two-story Banyan Tree with a bridge, a slide, wildlife play features and fenced areas. Completion is expected in July 2027, the same month as the pier.

Fifth Avenue Takes December

The Christmas Walk on Fifth Avenue South is shorter and centers on dinner. It runs Friday, December 4, from 5 to 10 p.m., and Saturday, December 5, from 10 a.m. to 10 p.m. The tree lighting begins around 6 p.m. on Friday. The BID still lists the day-long Christmas Market details as coming soon.

The big difference from Third Street is Avenue Dining. Participating restaurants serve dinner on the avenue during the walk, and reservations have to be made directly with each restaurant. This year's list:

1. Bistro 821
2. Caffe Milano
3. Casa Neri
4. Chops City Grill
5. DelMar
6. Keewaydin's
7. La Pescheria
8. La Trattoria
9. Le Colonial
10. Molto
11. Ocean Prime
12. Osteria Tulia
13. Ottimo on 5th
14. Pazzo
15. Sails
16. Slice Shop
17. Tulia Italian Steaks
18. Vergina

Third Street's evenings are open to anyone who walks up. A Friday table on Fifth means calling one of these 18 restaurants in November.

What the Avenue Looks Like When the Tree Goes Up

Fifth Avenue will greet December partly rearranged. Naples Press reported that Wind in the Willows moved to a side-street entrance at 675 Fifth Ave. S., with Faherty set to take its former corner. The former Regatta space was split for a flip-flop retailer and Spartina 449, and Johnnie-O also joined the avenue. In a separate Naples Press report, State & Liberty Clothing Co. opened in Suite 785 on October 12.

The 600 block will still be in transition. L'Olivo at 651 Fifth Ave. S. closed for façade work. Developer Derek Nagy of M Development told Naples Press it would return along with several other concepts. Restaurateur Feibi Gouda plans Riva Mediterranean Restaurant & Lounge at 651 Fifth and Zanu Sushi Bar next door. In a Naples Press column, she said permit delays had pushed the launch to after the 2026–27 season, likely 2027. So the 2027 opening date shared by the pier and the Cambier Park playground applies to this corner too.

For the Christmas Walk, the BID's parking page lists public garages at 8th Street South and 6th Avenue and at 8th Street South and 4th Avenue, plus a public lot at Park Street and 6th Avenue South. On the Third Street side, the pier lot is down to its western third this year. The Broad Avenue South and 13th Avenue South beach ends are now the main way to reach the sand from that part of town.

Every year, the holidays bring visiting family and friends to Old Naples. Sometimes, between the Third Street snowfall and the Fifth Avenue tree lighting, a visitor starts wondering what it would be like to have a place within walking distance of both. Karen Van Arsdale has watched these downtown seasons since 1981 and is glad to talk through which streets put you closest to how you like to spend them. Schedule a private consultation.