The Village Shops on Venetian Bay has one tree-lighting evening this year, but the snow falls twice. Grand Illuminations is this Saturday, November 21, and Holiday on the Bay is Saturday, December 12. Both run from 3 to 7 p.m., both have free photos with Santa, and both have a snow show along the bay at 6 p.m. Four smaller events fill the three weeks in between. Each one is aimed at a different crowd: runners, shoppers, people who come out for the Jingled Elves, and dog owners.
For anyone in Park Shore, that layout matters more than any single date. The headline evening has a repeat. The smaller dates come with their own hours, and they are easy to miss if you only remember the tree lighting.
Two Saturdays, Almost the Same Program
The Village posted its full holiday calendar on November 4. The two Saturdays are close enough that one works as a backup for the other.
| Grand Illuminations | Holiday on the Bay | |
|---|---|---|
| Date | Saturday, November 21 | Saturday, December 12 |
| Hours | 3 to 7 p.m. | 3 to 7 p.m. |
| Snow show | 6 p.m. | 6 p.m. |
| Santa photos | Complimentary | Complimentary |
| Music | Dickens Carolers | Holiday carolers |
| Extra | Festive character appearances | Family program along the decorated walkways |
The Village says the November evening is when what it calls Naples' tallest Christmas tree and more than 100,000 lights illuminate. On December 12, the second snow show takes place around the same tree, with the lights still glowing along the walkways. The first Saturday is the lighting itself. The second is a repeat of the same evening, which helps if you have guests arriving in mid-December or a November 21 that is already full.
Both nights put the snow show at 6 p.m., right at the dinner hour.
Thanksgiving Starts on the Bay at 7:20 a.m.
The first event after Grand Illuminations happens before most kitchens in Park Shore have started the turkey. The Gobble Gobble Thanksgiving Day 5K is on Thursday, November 26. Announcements begin at 7:20 a.m. and the race starts at 7:30. The Village describes a course that loops through its waterfront and onto nearby Naples streets. Runners, walkers, and anyone wearing a Thanksgiving costume are welcome. Registration goes through Run Elite Events.
The race supports St. Matthew's House. The Village says the tradition has raised thousands of dollars for the organization over the years. It is the first of two events on the calendar with a named charity attached.
The next morning, the hours change. Black Friday Stroll & Shop runs Friday, November 27 and Saturday, November 28 from 10 a.m. to 7 p.m., then Sunday, November 29 from noon to 6 p.m. There is no snow show and no Santa that weekend. Participating boutiques offer Black Friday deals, Small Business Saturday specials and other holiday discounts across fashion, shoes, jewelry, accessories, home décor and gifts. It is the one stretch of the season built around daytime shopping, not an evening outing.
Three December Nights, Three Different Crowds
The second week of December is the busiest part of the calendar, with three events in four days.
- Jingled Elves, Wednesday, December 9. The Village's stop time is still listed as TBD. The trolley tour itself runs from 4 to 9:30 p.m. and starts and ends on The Green at Mercato, 9110 Strada Place. Seats on the trolley for this 10th-anniversary tour are sold out, but Jingled Elves says everyone is welcome to come out and cheer. At The Village, the elves get off the trolley for dance routines set to holiday music, and The Village is a sponsor of the event.
- Santa Paws, Thursday, December 10, 4 to 7 p.m. This is the dogs' turn with Santa. Photos are free, and The Village suggests sweaters, bows, antlers or bandanas.
- Holiday on the Bay, Saturday, December 12, 3 to 7 p.m. The second snow show closes out the stretch.
The Jingled Elves stop is part of another organization's tour, and it connects the Park Shore waterfront to a group of charities across the county. Jingled Elves, Inc. is a 501(c)(3) that funds organizations serving women and children in Collier County, and its participants nominate and vote on where the money goes. The organization lists 15 grant recipients for 2026: Alliance for Period Supplies of SWFL, Baby Basics, Bikes for Tykes, Blessings in a Backpack of SWFL, Collier CAC, Collier Senior Center, Fostering Success, Grace Place, Harry Chapin Food Bank of SWFL, Laces of Love, Learn2Earn, Our Daily Bread Food Pantry, Pace Center for Girls, Partners for Breast Cancer and Youth Haven. Even though the trolley is full, you can still enter the organization's 2026 drawing.
The Village has a recent record of drawing crowds for a cause. Its Wine Around the Water evening on September 12 brought in more than 400 attendees and raised $17,800 for SNIP Collier. That was in the slow part of the year, before the holiday lights went up.
Where the 6 p.m. Snow Leaves You at Dinnertime
Look at when things happen. The 5K is over before breakfast. The Black Friday weekend runs during the day. Santa Paws starts at 4 p.m. On both Saturdays the snow begins at 6, an hour before the event ends. The Village's own event descriptions keep mentioning dinner. On November 21, it suggests a meal at "your favorite waterfront restaurant." After the elves perform, it points to "waterfront dining afterward."
The Village lists six full-service restaurants, plus a café and an ice cream shop.
- Bayside Seafood Grill & Bar serves seafood and grilled meats. It has an upstairs dining room above the bay and an outdoor Upper Deck Bar.
- Fish serves fresh seafood with Venetian Bay as the view.
- M Waterfront Grille serves New England-style steak and seafood, and every seat in the dining room looks out on the bay.
- MiraMare Ristorante serves Italian food at the water's edge.
- T-Michaels Steak & Lobster serves USDA Prime steaks and whole Maine lobsters, and it has an open-air atrium next to the bar.
- The Village Pub serves casual seafood, salads, sandwiches and heartier entrées, with seating inside and outside on the water.
The two smaller spots cover the hours on either side of dinner. Black Letter Coffee + Café is open daily from 8 a.m. to 4 p.m., which works for coffee after the Thanksgiving 5K or a break during the Black Friday weekend. It closes two hours before either snow show. Ben & Jerry's, which The Village calls the only Ben & Jerry's in Naples, is the after-dinner option for children who stayed up for the snow.
Put the restaurants and the calendar together and the season shapes up the same way each time. On both Saturdays, the snow falls at 6 p.m., during the dinner hour at the restaurants facing the water. On December 9, the elves' visit lands somewhere in a 4 to 9:30 p.m. window with no set time yet, so dinner on the bay is the easiest way to be there when the trolley arrives. The Village keeps current details on each event at venetianvillage.com and by phone at 239-261-6100.
For residents a few blocks away on Gulf Shore Boulevard North, the calendar gives two chances at the snow and two weeknights in December to stop in for whichever event fits. Nearby, Pelican Bay's beach restaurants are also starting the stretch when both serve dinner, a schedule we covered in October.
If this season's evenings on Venetian Bay have you thinking about a Park Shore address within walking distance of the tree, Abreu Group can walk you through what is available near The Village quietly and on your timeline. Schedule a Private Consultation.
