The Village on Venetian Bay Lights Up Twice This Season, Three Weeks Apart

This season, The Village Shops on Venetian Bay holds its signature holiday evening twice. Grand Illuminations on Saturday, Nov. 21, and Holiday on the Bay on Saturday, Dec. 12, have the same hours, the same lit tree and the same snow at 6 p.m. Smaller events fill the three weeks between them: a Thanksgiving morning race, a long shopping weekend and a Santa visit for dogs. For anyone living along Gulf Shore Boulevard North, the calendar comes down to choosing which Saturday evening to attend and which of the smaller events in between are worth a trip down the street.

Same Tree, Same Snow, Two Saturdays

On the Grand Illuminations event page, the season starts on Nov. 21 from 3 to 7 p.m. The evening includes complimentary photos with Santa, Dickens Carolers, costumed characters and decorated waterfront walkways. The tree, which the center calls the tallest Christmas tree in Naples, lights up along with more than 100,000 lights. The center's listing promises "a little Florida Christmas magic" at 6 p.m. in the form of a snow show.

Three Saturdays later, Holiday on the Bay uses nearly the same format. It also runs from 3 to 7 p.m., with free photos with Santa, character appearances, live holiday carolers and the same 100,000-plus lights, and the snow around the tree is again scheduled for about 6 p.m.

The main difference is timing. Nov. 21 comes five days before Thanksgiving, so it starts the season. Dec. 12 comes after the long holiday weekend and one week before the Naples Bay boat parade, so it falls in the busiest part of December. Neither listing mentions registration, a fee or special parking instructions. Both are open-door evenings at 4200 Gulf Shore Blvd. N.

If the snow is the reason you're going, plan to arrive before 6 p.m. Either evening works for Santa photos, since both include them at no charge.

Thanksgiving Morning Starts at 7:30

Five days after the tree is lit, the Village hosts an early-morning event. On Nov. 26, the Gobble Gobble Thanksgiving Day 5K begins at 7:30 a.m. Announcements start at 7:20, and the event is based at 4200 Gulf Shore Blvd. N. Elite Events organizes the race and lists this year's as the 25th annual. On its race page, Elite Events calls it "Naples' original Thanksgiving Day event" and describes a course through Naples streets and along the waterfront near the Village.

The race benefits St. Matthew's House. According to the organizer, the event has a long history of raising tens of thousands of dollars for the nonprofit. The race page quotes St. Matthew's House describing a "100% donation model": its social enterprises cover operating costs, so all public donations go to its programs.

Registering on Thanksgiving morning costs a little more, and there is no regular race-day packet pickup:

1. Price. Through Nov. 25, the organizer lists the 5K at $67 and family or group entries at $64. On race day, those prices rise to $69 and $66.
2. Packet pickup in Naples. Restore Hyper Wellness Naples hands out packets on Monday, Nov. 23, and Wednesday, Nov. 25, from 4 to 6 p.m.
3. Packet pickup in Fort Myers. Poke Fusion has a pickup on Tuesday, Nov. 24, from 4 to 6 p.m.
4. Emergency pickup. For anyone who misses those windows, emergency pickup runs from 6:25 to 7:10 a.m. on race morning.
5. On site. Parking is available throughout the Village Shops, and restrooms are near the start and finish.

Elite Events also posts an interactive course map and a flyover video of the route, so runners can see in advance which nearby streets the course uses. The Village's listing has the event ending at 11 a.m., which leaves the rest of the day for Thanksgiving dinner.

The Long Weekend Shifts the Hours

The day after the race, the Village moves into a three-day shopping weekend. According to the Black Friday and Small Business Saturday listing, shops are open from 10 a.m. to 7 p.m. on Friday, Nov. 27, and Saturday, Nov. 28, then from noon to 6 p.m. on Sunday, Nov. 29. Participating boutiques are offering savings throughout the weekend.

The 7 p.m. close on Friday and Saturday leaves time to finish shopping as it gets dark and then walk to dinner on the water without moving the car.

December 10 Is for the Dogs

Between the two big Saturdays, the Village has one weeknight event. Santa Paws runs on Thursday, Dec. 10, from 4 to 7 p.m., with complimentary photos of dogs with Santa. The listing invites owners to shop and dine afterward.

Santa Paws comes two days before Holiday on the Bay, so the same week offers a Thursday photo with the dog and a Saturday evening with the tree and the snow.

Where Dinner Fits Into the Evening

Both Saturday evenings run from 3 to 7 p.m., so dinner naturally comes after the 6 p.m. snow. On a page published Oct. 14, 2026, the center lists six waterfront restaurants on the bay.

• Bayside Seafood Grill & Bar
• Fish Restaurant
• M Waterfront Grille
• MiraMare Ristorante
• T-Michaels Steak & Lobster House
• The Village Pub

The Saturday events end at 7 p.m., Black Friday weekend shopping runs until 7 p.m. on Friday and Saturday, and Santa Paws invites guests to dine afterward. Any of those evenings can end with a reservation at one of these six restaurants.

One Week Later, the Parade Moves to Naples Bay

After Dec. 12, December's next big evening event moves to Naples Bay. According to the Marco Island Area Chamber of Commerce's event listing, the Naples Bay Christmas Boat Parade runs on Saturday, Dec. 19, from 6:15 to 8:30 p.m. The listed viewing spots include Naples City Dock, Tin City, Riverwalk Restaurant, Naples Landing, Kelly's Fish House, The Boat House on Naples Bay and Bayview Park.

That puts three December Saturdays in a row on the calendar. The Village's evening is on the 12th, the boat parade is on the 19th, and Christmas comes the following weekend. For a Park Shore household that wants one evening on Venetian Bay and one on Naples Bay this December, the two dates fall a week apart.

From the Nov. 21 lighting through Dec. 19, the season looks like this:

The Village also posts its full schedule on its events calendar, which can be subscribed to from Google Calendar, iCalendar or Outlook.

Living a short walk from these evenings on Venetian Bay is part of what a Park Shore address is worth. If you'd like to see how the market values yours this season, Laurie Bellico is glad to help. Get your instant home valuation and have a quiet conversation whenever you're ready.