When does the holiday season start in Olde Naples? It depends on which street you're standing on. Third Street South lights its tree on Monday, November 23. Fifth Avenue South lights its own on Friday, December 4. The City of Naples holds its parade four days after that. The last big event of the season happens on the water, on a Saturday in late December, and finishes in a cove in Port Royal.
The schedule has gaps because no single group runs it. Third Street South's merchants, the Fifth Avenue South district, the City of Naples and the Marco Island Area Chamber of Commerce each publish their own calendar, so the season moves from one street to the next instead of happening everywhere at once. If you live within walking distance of all of it, you need to know the order.
Third Street Goes First, and Changes Its Hours Partway Through
The 49th Annual Christmas on Third opens 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 rest of Thanksgiving week keeps a steady schedule. Tuesday through Saturday, there's live music from 5 to 8 p.m., snowfall at 7 p.m., and shops stay open until 7 p.m. There's no programming on Thanksgiving Day itself, Thursday, November 26.
Once December starts, the schedule narrows. The December Holiday Magic program runs December 3 through December 24 on fewer nights.
| Thanksgiving week, Nov. 24–28 | December, Dec. 3–24 | |
|---|---|---|
| Live music, 5–8 p.m. | Tuesday through Saturday | Thursdays and Fridays |
| Snowfall, 7 p.m. | Tuesday through Saturday | Thursday through Saturday |
| Shops open | Until 7 p.m. | Until 7 p.m. |
| Day with no programming | Thanksgiving Day | Christmas Day |
So a Tuesday walk to see the snowfall works the week of Thanksgiving and doesn't work again in December. That difference shapes the rest of the month on Third Street.
New this year, Third Street South has been named a North Pole Delivery District. Children can pick up an official Letter to Santa at participating shops from November 25 through December 23. There are two mailboxes for the letters, one at Fleischmann Plaza near Gattle's and one at Santa's Workshop near Sea Salt. Sea Salt is also where Santa Paws happens on Saturday, December 12, from 1 to 3 p.m., with photos with Santa and Mrs. Claus.
The Saturday After Thanksgiving Fills the Whole Day
Saturday, November 28 has more going on downtown than any other day of Thanksgiving week. The Third Street South Farmers Market comes back for the winter season that morning, 7:30 to 11:30 a.m., on Third Street South between Broad and 13th Avenue South. It runs every Saturday after that. The market describes itself as connecting local growers and independent agricultural merchants with local buyers, with no national chains or franchises.
That same Saturday, Art in the Park fills Cambier Park from 10 a.m. to 4 p.m. It's still Thanksgiving week on Third Street, so the 7 p.m. snowfall closes out the day. That's one Saturday with a morning market, an afternoon art show and an evening snowfall, all within the same few blocks.
Cambier Park has one more art weekend before that. The Naples Artcrafters Fine Arts & Craft Show is Saturday, November 14, from 10 a.m. to 4 p.m.
December 4 Is the Night Both Streets Run at Once
Fifth Avenue South's Christmas Walk and Tree Lighting runs Friday, December 4, from 5 to 10 p.m. The tree lighting begins at about 6 p.m. The event continues Saturday, December 5, from 10 a.m. to 10 p.m.
December 4 is a Friday, and that puts it inside Third Street's December schedule. Live Christmas music plays on Third Street from 5 to 8 p.m., and the snowfall comes at 7. On Fifth Avenue, the tree is lit about an hour before that. For one evening, both shopping streets have programming at the same time. Saturday, December 5 overlaps too, since Third Street's snowfall runs Saturdays in December while Fifth Avenue keeps going until 10 p.m.
Fifth Avenue South lists the restaurants serving dinner on the Avenue during the festivities, and reservations go directly through each restaurant:
- Bistro 821
- Caffe Milano
- Casa Neri
- Chops City Grill
- DelMar
- Keewaydin's
- La Pescheria
- La Trattoria
- Le Colonial
- Molto
- Ocean Prime
- Osteria Tulia
- Ottimo on 5th
- Pazzo
- Sails
- Slice Shop
- Tulia Italian Steaks
- Vergina
On a Friday that brings in crowds from beyond Olde Naples, that list is the practical way to plan a dinner around a 6 p.m. tree lighting and still make it to the 7 p.m. snowfall on Third.
Sunday Shifts to the Parks
The weekend ends away from both shopping streets. On Sunday, December 6, at 2 p.m., the Naples Concert Band plays "Travel, Tradition & Timeless Holiday Favorites" at Cambier Park. The band's concerts are free, with a suggested contribution of $10.
The same date is on the City of Naples' 2026 event calendar for a Chanukah Festival at Baker Park. Sunday's events are spread between two parks, after a Friday and Saturday spent on two streets.
December 8, the Parade Connects Both Streets
Third Street South and Fifth Avenue South each run their own programs. The City of Naples Christmas Parade is the one event built to cover both. It begins Tuesday, December 8, at 6:30 p.m., at the corner of Third Street South and Ninth Avenue South. From there it heads up to Fifth Avenue South and finishes on Eighth Street South in front of City Hall. The city's listing promises floats, marching bands, holiday music, performers and an appearance by Santa Claus.
The route ties the season's pieces together. It starts in the Third Street district that lit the first tree on November 23, crosses over to Fifth Avenue, which lit its tree four days earlier, and ends at City Hall. It's also a Tuesday, a night Third Street doesn't have snowfall in December, so the parade has the evening to itself.
December 19, the Season Moves Onto the Bay
The last big event of the season leaves the streets for Naples Bay. MIACC's Christmas Boat Parade on Naples Bay runs Saturday, December 19, from 6:15 to 8:30 p.m. Naples City Dock hosts the parade, the judges and VIP guests.
According to the chamber's 2026 press release, the route goes like this:
- Boats start at Marker 18, near Bayview Park and Hamilton Harbor.
- The parade travels north to Naples City Dock and Pincher's at Tin City.
- It then turns south into Port Royal's Man-O-War and Morgan Cove.
Naples City Dock sits in Crayton Cove, at the bay edge of Olde Naples. Viewing at the dock is ticketed. MIACC also lists Pincher's at Tin City, Riverwalk Restaurant, Naples Landing, Kelly's Fish House, The Boat House on Naples Bay and Bayview Park as viewing sites.
The season's large events opened on Third Street on November 23 and wrap up nearly four weeks later in the canals of Port Royal. Even then, Third Street keeps its Thursday-through-Saturday snowfall going until the December Holiday Magic schedule ends on December 24.
Getting Around After Dark
Most of these events start around sunset or later, and that matters for getting there. On Fifth Avenue South's parking and transit page, the Naples Trolley runs daily from 8:30 a.m. to 5:30 p.m. That means it stops running before the Fifth Avenue tree lighting, the Third Street snowfall and the city parade. The same page lists parking garages on Eighth Street South at Sixth Avenue and at Fourth Avenue, plus a public lot at Park Street and Sixth Avenue South. For anyone who lives in Olde Naples, walking is the most reliable way to get to all of it.
Here's the order in brief. Third Street opens November 23 and runs a full schedule through Thanksgiving week. December 4 and 5 bring both streets out at once. December 6 moves to Cambier and Baker parks. December 8 sends the parade from Third Street up to Fifth Avenue and City Hall. December 19 takes the season out onto Naples Bay. Third Street keeps its snowfall nights going through December 24.
At Kaleena Figaro Group, we follow Olde Naples nights like these the same way our clients do, block by block and date by date. If you're weighing how close you'd like to live to Third Street South, Fifth Avenue South or the bay, we're happy to walk the parade route with you this December. Start Your Naples Home Search.
