What do you skip when the tree lighting, Handel's Messiah and a brass band all fall in the same two days? From Oakmont's lakeside streets in Pelican Bay, the holiday calendar sits along one corridor. Artis-Naples is at 5833 Pelican Bay Boulevard, Mercato is at the corner of U.S. 41 and Vanderbilt Beach Road, and The Ritz-Carlton, Naples is at 280 Vanderbilt Beach Road. This year, all three put their biggest holiday events into two short stretches, Dec. 2 to 8 and Dec. 17 to 24. Nights in those weeks are crowded, and the days between them are fairly open.
Below is the calendar in order, with the overlaps marked. Use it to settle on a few nights early.
The November warm-up is mostly at Mercato
The weeks before Thanksgiving belong to Mercato's regular monthly events, which this month carry holiday themes. Here's what remains after this post goes up:
- Films Al Fresco ft. A Christmas Story, Tuesday, Nov. 17. The outdoor movie runs at dusk on the third Tuesday of each month, and the listing carries the series through Dec. 15.
- PAWty in the Piazza ft. Caloosahatchee Philharmonic, Thursday, Nov. 19. Live music and drinks on the piazza, with dogs welcome.
- Social Hour for a Cause, Tuesday, Nov. 24. Held at Waxin's, with sales going to Big Brothers Big Sisters of the Sun Coast.
- Thanksgiving at Mercato, Thursday, Nov. 26. Restaurant offerings are posted on Mercato's events page.
For a hosted Thanksgiving meal, The Ritz-Carlton, Naples lists its Thanksgiving Grand Buffet on Nov. 26 from 10 a.m. to 2 p.m. It's led by Executive Chef Efe Salar and includes a separate children's buffet. At Waterside Shops, the earliest charity date is a Shop & Share supporting AVOW on Friday, Nov. 13.
Week one: Dec. 2 to Dec. 8, when both ends of the corridor fill up
The first cluster starts on a Wednesday at Mercato and moves to Hayes Hall the next night, part of the Artis-Naples 2026–27 season announced in April.
| Date | Mercato, 9110 Strada Place | Artis-Naples, 5833 Pelican Bay Blvd. |
|---|---|---|
| Wed., Dec. 2 | Tree Lighting Ceremony & Holiday Cirque Experience, 5:30 to 8 p.m. | |
| Thu., Dec. 3 | Mercato Nights Music Series ft. Empire Strikes Brass | Handel's Messiah, 7:30 p.m., tickets from $29 |
| Sat., Dec. 5 | The Nutcracker, 7 p.m.; Baron Wolman exhibition opens at The Baker Museum | |
| Sun., Dec. 6 | Festivals of Speed | The Nutcracker, 2 p.m. and 7 p.m. |
| Tue., Dec. 8 | Hanukkah Celebration on the Event Lawn |
Mercato's tree lighting runs on a timetable. Dance students from Dance Arts by Maria and Naples Dance Conservatory perform on the piazza from 5:30 to 6 p.m. Electric violinist Siobhan Cronin and Cayman play from 6 to 8 p.m., and the tree is lit at about 7 p.m. Cirque acts on silks, lyra and cyr wheel rotate on the Event Lawn the whole evening, and The Pub runs an outdoor bar. Activity Row hosts the holiday market, with face painting, hot cocoa and gifts. Parking is free in the Main Mercato Garage. Event parking is also available at the 999 Vanderbilt Garage, at U.S. 41 and Vanderbilt Beach Road, for $12.
The next night, the music moves south. Associate Conductor Manuel López-Gómez leads the Naples Philharmonic, the Naples Philharmonic Chorus and guest soloists in Handel's Messiah at Hayes Hall. Mercato's monthly Mercato Nights show with Empire Strikes Brass is the same evening.
Opening weekend of Naples Ballet's The Nutcracker brings the busiest Saturday of the stretch. Naples Ballet's student dancers perform with professional soloists from Miami City Ballet, and the Naples Philharmonic plays the Tchaikovsky score. The Baker Museum also opens Baron Wolman: Capturing the Sound of an Era that Saturday, Dec. 5, and it runs through June 13, 2027. A Sunday matinee of the ballet falls on the same day as Festivals of Speed, Mercato's display of vintage and contemporary cars.
The week ends on Tuesday, Dec. 8, with Mercato's Hanukkah Celebration on the Event Lawn, hosted with the Jewish Federation of Greater Naples.
The quieter middle carries one thread from Mercato to Waterside
After the eighth, the corridor quiets for a few days. One cause connects the two clusters. At the Dec. 2 tree lighting, the Guadalupe Center runs a toy drive at the holiday market, and Mercato's event page links to the center's Holiday Gift Shop wish list. Nine days later, on Friday, Dec. 11, Waterside Shops holds its Guadalupe Center Toy Drive and Shop & Share.
That weekend also starts the daytime events at The Ritz-Carlton, Naples. Teddy Bear Tea is on Dec. 12 and 13, from 2:30 to 4:30 p.m. Children leave with a keepsake bear, according to the resort's holiday page. The resort's life-size Gingerbread House, made by the pastry team under Executive Pastry Chef Lerome Campbell, is viewed by reservation through the same page.
Week two: Dec. 17 to Dec. 24, when the matinees take over
The second cluster leans toward afternoons and families. It starts with two events on the same Thursday.
- Holiday Pops at Hayes Hall, Dec. 17 to 20. Shows are Dec. 17 and 18 at 7:30 p.m., Dec. 19 at 2 p.m. and 7:30 p.m., and Dec. 20 at 2 p.m. Guest conductor Nicholas Hersh leads the Naples Philharmonic, the Naples Philharmonic Chorus and the Naples Philharmonic Youth Chorus.
- Santa Paws at PAWty in the Piazza, Dec. 17. Mercato's monthly dog-friendly evening gets a holiday version on the same night as the first Holiday Pops show.
- Teddy Bear Tea, Dec. 18 to 22. The Ritz-Carlton's second round runs 11 a.m. to 4:30 p.m.
- Breakfast with Santa, Dec. 22 to 24. It's listed at The Ritz-Carlton, Naples for the three days before Christmas, with a holiday buffet and music.
The Holiday Pops ticket covers more than the concert. It includes same-day admission to The Baker Museum, which has special hours on performance days: 10 a.m. to 7:30 p.m. on Dec. 17 to 19, and noon to 4 p.m. on Dec. 20. Hayes Hall doors open 60 minutes before each show, and Heidi's Place serves light fare. General museum admission is $10 for adults, $5 for full-time students and free for anyone 17 and under, so the bundled ticket matters most for adults.
That museum time also falls near the end of one show. Linling Lu: Fugue in 3 Voices closes Jan. 3, 2027. The same visit covers The Surrealist International: Fifty Years of Dreams, which runs to Feb. 14, 2027, and Florida Contemporary 2026–27. A Holiday Pops matinee can be your last chance at the Linling Lu show without a separate trip.
Waterside is mid-change this December
Waterside Shops is the closest center to the south, and this season it's working through a lot of tenant changes. Vuori opened in September near Sephora at 5475-7 Tamiami Trail N. Anthropologie is moving within the center to 5475-1 Tamiami Trail N. Eddie V's Prime Seafood, which Waterside named among its new dining options this spring, lists its Naples restaurant near the center at 765 Seagate Drive, with evening hours starting at 4 p.m.
Two larger projects are on a later schedule. Buck & Rider, the seafood concept taking over Brio's former space, is hiring managers now. Hi Noon Hospitality's hiring page gives an early 2027 opening. On the former Nordstrom site at 5489 Tamiami Trail North, RH is building a single-story store with six galleries and a 174-seat restaurant under a glass atrium. Hoodline reported in October that construction was underway, with a late-2026 opening target. This season, Waterside's dated events are its two charity days, Nov. 13 and Dec. 11, and Mercato and Hayes Hall carry the big seasonal shows.
After the 24th, the calendar thins out
Christmas week is fairly empty on these calendars. The main dated event left is New Year's Eve at The Ritz-Carlton, Naples. Its Signature Soirée includes a five-course menu, unlimited premium beverages, the 11-piece Manhattan Band and a champagne toast at midnight, and it's limited to guests 18 and older. On Hayes Hall's posted schedule, nothing runs from the end of December until the Jan. 5 listings. Mercato starts again on Jan. 7 with Mercato Nights featuring Unlimited Devotion. Its 4th Annual Mercato Art Celebration is Jan. 23 and 24, with artists set up along Strada Place.
Venues sometimes change times and sell out shows, so check each event's own page before you set your plans.
Hosting family during these two weeks often gets people thinking about home and what's next. If it does, Chad Phipps knows Oakmont and the Pelican Bay corridor well and can talk through what your home is worth this season. Ask for an instant home valuation and a local market consultation before the busy weeks start.
