Photo: proshob / Wikimedia Commons · CC BY-SA 3.0 · cropped
NAPLES, FLORIDA · THE 2026–27 SEASON
Naples This Season
From the first tree lighting in November to the last art fair in April, season is when Naples is most itself — festivals, concerts, parades and markets stacked week after week. This is the calendar we keep for our own clients: the signature dates checked against the organizers, the neighborhood favorites close to North Naples first, and the handful of tickets worth booking before they sell out. We refresh it monthly, all season long.
DATES CHECKED AGAINST THE ORGANIZERS · NOVEMBER 7, 2026 · REFRESHED MONTHLY
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✦ BOOK SOON — THE SHORT LIST ✦ Johnsonville Night Lights in the Garden — timed tickets are on sale now and the best evenings go first (Nov 27–Jan 3). Hamilton at Artis—Naples — Nov 24–29, and the run is nearly gone. Cars on 5th, on Bayshore Drive — Feb 6; fewer tickets are being sold at the new venue. Christmas Boat Parade dock seats — Dec 19; shore viewing is free, the Naples City Dock seats are ticketed and limited. Chubb Classic — Feb 12–14 at Tiburón; the anniversary-year grounds passes are on sale now. |
Close to home — the North Naples anchors
Start with the four calendars closest to Pelican Bay and Park Shore — most of the season happens within fifteen minutes of Vanderbilt Beach.
Photo: Tomás Del Coro / Wikimedia Commons · CC BY-SA 4.0
Mercato. The free Mercato Nights music series runs the first Thursday of the month on the Event Lawn — Empire Strikes Brass on December 3, 6:30–8:30pm; bring a chair. Cars & Coffee 239 fills the streets on third Sunday mornings (Nov 15, Dec 20), and Films Al Fresco screens A Christmas Story in the Piazza on November 17.
Waterside Shops. Waterside runs store-level events rather than one big center festival — the season's community date is the Guadalupe Center's Gift of Giving toy drive and Shop for Education day at the Pavilion on Friday, December 11, noon–4pm. Free to attend; bring a new unwrapped toy or a donation.
Artis—Naples. Pelican Bay's own concert hall carries a season most cities would envy: Hamilton (Nov 24–29), Handel's Messiah (Dec 3), Holiday Pops (Dec 17–20), Death Becomes Her (Dec 29–Jan 3), Renée Fleming and Thomas Hampson (Jan 7 & 9), the Cleveland Orchestra (Jan 26 & 31), The Great Gatsby (Feb 2–7), the Munich Philharmonic with Anne-Sophie Mutter (Feb 15), and the London Symphony Orchestra (Mar 9), with Beethoven's Ninth on Mar 20. Every ticket includes same-day admission to The Baker Museum.
Photo: Daderot / Wikimedia Commons · CC0
Naples Botanical Garden. Johnsonville Night Lights in the Garden runs November 27–January 3 (closed Dec 24, 25 & 31) — the Garden lit end to end, on timed tickets: non-members $36 early season, $42 at peak. Go on a weeknight in early December for the smallest crowds. The Garden also hosts the Naples Orchid Show in February (below).
✦ THE SEASON OPENS
Photo: Franz Stellbrink / Wikimedia Commons · CC BY 3.0
November 2026
The season wakes up — the first evenings out, the first lights going up.
Thu Nov 12 — Evening on Fifth. Live music, dining and open-air shopping up and down Fifth Avenue South, 6:30–9:30pm, free. It returns all season: Dec 10, Jan 14, Feb 11, Mar 11 and Apr 8.
Sat Nov 14 — USA TODAY Wine & Food Experience. One-ticket tastings from dozens of Naples restaurants at Paradise Coast Sports Complex, noon–4pm. $75, bought online in advance.
Nov 19–22 — CME Group Tour Championship. The LPGA season finale at Tiburón Golf Club — the top 60 players in women's golf, ten minutes from North Naples. Grounds passes $40 a day.
Mon Nov 23 — Christmas on Third. The 49th annual tree lighting on Third Street South, 6–9pm, with Santa and snowfall; music and snowfall evenings continue through the holidays.
Nov 24–29 — Hamilton at Artis—Naples. The Broadway tour's Thanksgiving-week run in Hayes Hall. Book soon — see Close to Home, above.
Photo: Naples Botanical Garden
Fri Nov 27 — Johnsonville Night Lights in the Garden opens. Naples Botanical Garden, nightly through January 3 on timed tickets. Book soon — see Close to Home, above.
Sat Nov 28 — Art in the Park. Juried art in Cambier Park, downtown — the season's first edition of a series that returns Feb 6 and Apr 10.
✦ HOLIDAY NAPLES
Photo: Third Street South
December 2026
The lights come on — and so does everyone you know.
Thu Dec 3 — Handel's Messiah & Mercato Nights. The Messiah at Artis—Naples in the evening; the free Mercato Nights concert (Empire Strikes Brass) on the Event Lawn, 6:30–8:30pm. Pick one — or start at Mercato and make it an early night.
Dec 4–5 — 5th Avenue Christmas Walk & Tree Lighting. Sugden Plaza and the avenue: a living nativity, skating rink, live music and Santa, 5–10pm Friday. Free.
Tue Dec 8 — Naples Christmas Parade. Downtown's hometown parade, 6:30pm. Free.
Fri Dec 11 — Gift of Giving at Waterside Shops. The Guadalupe Center toy drive and Shop for Education day, noon–4pm at the Pavilion. See Close to Home, above.
Dec 17–20 — Holiday Pops at Artis—Naples. The Naples Philharmonic's Christmas tradition in Hayes Hall.
Photo: Marine Industries Association of Collier County (MIACC)
Sat Dec 19 — Christmas Boat Parade on Naples Bay. The 37th parade of lit boats, 6:15–8:30pm, theme "Blossoms & Bows" — note the date: it moved to December 19 this year. Viewing is free from Bayview Park, Tin City and the Riverwalk; Naples City Dock seats are ticketed and limited. Book soon for the dock.
Dec 29–Jan 3 — Death Becomes Her at Artis—Naples. The Broadway musical comedy closes the year in Hayes Hall.
✦ PEAK SEASON BEGINS
Photo: Naples Art Institute
January 2027
Art takes the streets — and the boats, blooms and bass lines arrive.
Jan 2–3 — Naples New Year's Art Fair. The first major juried fair of the year, Cambier Park and Park Street, 10am–5pm.
Jan 7 & 9 — Fleming and Hampson at Artis—Naples. Renée Fleming and Thomas Hampson in recital — two nights only, and they will not last.
Jan 9–10 — Bonita Springs National Art Festival, Show 1. 200-plus juried artists in Riverside Park, Bonita Springs; $10 suggested donation. Shows 2 and 3 follow Feb 6–7 and Mar 6–7.
Jan 15–17 — Tamiami International Orchid Festival. A day trip, not a Naples event: the largest winter orchid festival in the country, at the Miami-Dade County Fair Expo Center. $20 at the door, children under 12 free.
Jan 21–24 — Naples Boat Show. Boats on land at Sugden Regional Park and in the water at Naples City Dock, with a free shuttle between. $15 in advance, $20 at the gate; children 12 and under free with a paying adult. Buy tickets →
Sun Jan 24 — Swamp Buggy Winter Classic. Swamp buggies racing through the mud at Florida Sports Park — pure Naples, unlike anything else on this calendar. (The parade runs the day before.)
Jan 26 & 31 — The Cleveland Orchestra at Artis—Naples. Two visits in one week from one of the world's great orchestras.
Jan 29–31 — Naples Winter Wine Festival. The Ritz-Carlton Naples, Tiburón hosts one of America's top charity wine auctions. Whole-festival packages are by inquiry only — it sits in a category of its own.
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✦ SEASON SPOTLIGHT ✦ February 19–21, 2027 · St. Katherine Greek Orthodox Church, 7100 Airport-Pulling Road N. Three days of Greek food, live music and traditional dancing — the season's flagship food festival, fifteen minutes from Pelican Bay. One honest note: the church has published the 2027 dates, but admission and hours were not yet posted when we checked (November 7, 2026). Historically it has been a walk-up event; we will update this page the moment the details land. Opa! |
✦ THE BIGGEST MONTH
Photo: kitmasterbloke / Flickr · CC BY 2.0
February 2027
The biggest month of the season — four festivals share one long weekend.
One weekend, four festivals — pick your two. February 19–21 stacks the Greek Festival, the Naples National Art Fair, the Naples Orchid Show and the Everglades Seafood Festival onto the same three days. Nobody does all four well; the calendar below has each one.
Feb 2–7 — The Great Gatsby at Artis—Naples. The Broadway musical in Hayes Hall.
Feb 4–7 — Cars on 5th & the Naples Automotive Experience. The main concours is Saturday, February 6, 10am–4pm — on Bayshore Drive in East Naples, not Fifth Avenue: the show moved after the city declined the 2027 Fifth Avenue permit. 750-plus cars; organizer-reported prices start at $50, and fewer tickets are being sold at the new venue. Book soon. The weekend also brings a Jay Leno charity comedy night (Feb 4, Hertz Arena) and the Jetport Reception (Feb 5).
Feb 6–7 — Bonita Springs National Art Festival, Show 2 — and Art in the Park's winter edition in Cambier Park on Feb 6. A three-way Saturday with the car show; choose by passion.
Feb 12–14 — Chubb Classic at Tiburón. The PGA Tour Champions' 40th anniversary edition on the Black Course: $20 Thursday, $40 a day Friday–Sunday, $100 for the week. Book soon for the best days.
Mon Feb 15 — Munich Philharmonic at Artis—Naples. Anne-Sophie Mutter joins the orchestra for one night.
Feb 19–21 — Naples Greek Festival. St. Katherine Greek Orthodox Church — see the spotlight above.
Feb 19–21 — Naples National Art Fair. The 48th edition of Naples' premier juried fair: some 200 artists across Cambier Park and Park Street, Friday evening through Sunday.
Photo: Daderot / Wikimedia Commons · CC0
Feb 19–21 — Naples Orchid Show & Sale. The Naples Orchid Society's "Orchid Fiesta" at Naples Botanical Garden, included with Garden admission (members free).
Feb 19–21 — Everglades Seafood Festival. Stone crab, swamp cabbage and live music in Everglades City, about 35 minutes away — the most Old Florida day on this list. Friday evening entry by canned-food donation; Saturday and Sunday a $10 minimum donation.
Sat Feb 27 — A new car show takes Fifth Avenue. A separate, free community show of some 400 cars fills the avenue the big show vacated; its name was still to be announced when we checked.
✦ OPERA UNDER THE STARS
Photo: CTNMM82 / Wikimedia Commons · CC BY-SA 4.0
March 2027
Concert season at full stretch — the great orchestras are in town.
Mar 6–7 — Bonita Springs National Art Festival, Show 3. The final Riverside Park edition of the season.
Tue Mar 9 — London Symphony Orchestra at Artis—Naples. Sir Antonio Pappano conducts, Maxim Vengerov solos — one night.
Mar 18–25 — Opera Naples: Festival Under the Stars. Outdoor opera in Baker Park on the Gordon River: The Barber of Seville (Mar 18 & 20), a Menotti triple bill (Mar 19 & 21) and I Pagliacci (Mar 24 & 25), all at 7:30pm. Reserved seats $39–$157; tickets are on sale.
Sat Mar 20 — Beethoven's Ninth at Artis—Naples. The full Beethoven cycle at Hayes Hall closes with the Ninth.
Mar 20–21 — Naples Downtown Art Fair. The 39th edition fills Cambier Park, 10am–5pm.
✦ THE SEASON WINDS DOWN
Photo: scott.zona / Wikimedia Commons · CC BY 2.0
April 2027
Last call for season — make it count.
Sat Apr 3 — Swamp Buggy Coors Banquet Cup Finals. The season's mud-racing championship at Florida Sports Park.
Thu Apr 8 — Evening on Fifth. The season's last edition of the avenue's music-and-dining night.
Apr 9–10 — Mendelssohn's Italian Symphony at Artis—Naples. Spring sunshine, in orchestral form.
Sat Apr 10 — Art in the Park (Spring). The Cambier Park series closes its season — and the Saturday markets below roll on into May.
✦ EVERY SATURDAY
The two Saturday markets
Photo: Third Street South
Vanderbilt Farmers Market — the close one. Every Saturday, 8am–1pm, rain or shine, at the Galleria Shoppes at Vanderbilt (2355 Vanderbilt Beach Road) — five minutes from Pelican Bay. The largest and longest-running market in North Naples, 90-plus vendors in season, running through May 22, 2027. Free entry.
Third Street South Farmer's Market — the Old Naples one. Every Saturday, 7:30–11:30am. From mid-November through April it sets up on Third Street itself, between Broad and 13th Avenues — some 60 curated food vendors. Go early, then stay for breakfast and the shops.
✦ MORE THAN A VISIT?
Planning a season of your own
Most people meet this calendar as visitors and end up reading it as future neighbors. If that is where your thinking is headed, start with our 55 community guides — fees, rental rules and market notes for every Naples neighborhood on this page — then check the Naples market report, refreshed monthly from the official NABOR data, and our guide to buying in Naples.
A note on dates: events move. We check this calendar against the organizers when we build it and again at every monthly refresh — the "dates checked" line at the top is the honest as-of date, and anything we could not confirm is labeled or left out.
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✦ QUESTIONS ABOUT THE SEASON — OR A HOME IN IT? ✦ Call or text (239) 216-2016 Coming to Naples for the season — or thinking about a home here? I am happy to help with either. MICHAEL O'REILLY · REALTOR® AND BROKER ASSOCIATE, DOWNING-FRYE REALTY, INC. · OS FLORIDA GROUP |