Welcome to September. Season is still weeks away, the roads are still quiet, and this is the stretch of year when Naples belongs to the people who live here full-time. Sizzle Dining launched Monday — 140 restaurants offering prix-fixe menus all month. A sharp comedian opens Off the Hook Thursday. Free Zoo Day is Saturday. And the weekly community staples that make this city worth living in are all running. Here's the full week.
🍽️ Running All Month — Sizzle Dining 2026
September 1–30 | 140+ restaurants across Lee and Collier counties
🌐 sizzledining.org | No reservation required through the program — book directly with restaurants
Naples' signature September dining event is underway. For every Sizzle Dining meal sold, participating restaurants donate $1 to Blessings in a Backpack, which feeds food-insecure Collier County elementary students on weekends and during the summer.
Prix-fixe menus range from $19 for a 2-course lunch up to $69 for a 3-course dinner. Browse the full restaurant list and menus at sizzledining.org before you go — menu quality and value varies significantly by restaurant.
NNN tip: Before you order, ask your server whether the Sizzle Dining portions are the same size as the regular menu. You deserve a straight answer before you commit. Then email us at [email protected] with "Sizzle Dining" in the subject line to tell us what you found.
Also running in September on Fifth Avenue South: Flavors of Fifth through September 30 at 14 participating restaurants. Browse at fifthavenuesouth.com.
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🗓️ Thursday, September 3
😂 Shayne Smith and Mike Abrusci — Off the Hook Comedy Club📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples
🕖 7:00 PM | 🎟 Tickets at offthehookcomedy.com | 239-389-6901
Shayne Smith opens a weekend run at Off the Hook Thursday evening alongside Mike Abrusci. Known for his tattooed rockstar look and unexpectedly sharp introspective comedy, Smith has built a significant following through social media and touring — his comedy disarms audiences with self-awareness and precision timing. A strong opener for the first full week of September.
🗓️ Friday, September 4
😂 Shayne Smith and Mike Abrusci — Two Shows📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples
🕡 6:30 PM & 8:30 PM | 🎟 offthehookcomedy.com
Two shows Friday. The 6:30 PM show pairs well with an early Sizzle Dining reservation. The 8:30 PM set gets the later crowd. Both are the same performers — different energy depending on who fills the room Friday night.
🍔 Shake Shack — Grand Opening Day📍 6833 Collier Blvd., Restaurant Row Naples
🕙 Opening day — check shakeshack.com for hours
Naples' second Shake Shack opens its doors today at Restaurant Row Naples with inside dining and a drive-thru. Hand-spun milkshakes, ShackBurgers, and crinkle-cut fries — now with a drive-thru option in East Naples. Expect a line on opening day.
🗓️ Saturday, September 6 — Biggest Day of the Week
🛍️ Third Street South Farmers Market📍 Third Street South, downtown Naples
🕖 7:30 AM – 11:30 AM | 🎟 Free
The 30-year Saturday institution in Old Naples returns for its first weekend of September. Fresh produce, baked goods, local vendors, and strong coffee in the heart of downtown. Start here.
🦁 Free Zoo Day — Collier County Residents📍 Naples Zoo at Caribbean Gardens, 1590 Goodlette-Frank Road, Naples
🕘 Opens 9:00 AM | Entry available until 3:30 PM | 🎟 Free with Collier County photo ID | napleszoo.org | 239-262-5409
The first Saturday of every month, Collier County residents get free all-day admission to the Naples Zoo. Bring a matching photo ID with your Collier County address. Entry closes at 3:30 PM — plan accordingly.
The Naples Zoo at Caribbean Gardens features big cats, primates, giraffes, and the unique tram-guided boat tour through islands of free-ranging primates. For families with children, this is the best value event of the week. Go early for the cooler morning temperatures and shorter lines.
😂 Shayne Smith and Mike Abrusci — Two Shows📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples
🕕 6:00 PM & 8:00 PM | 🎟 offthehookcomedy.com
Final weekend night for Shayne Smith's Naples run. Two shows Saturday — 6 PM and 8 PM. The Saturday night shows are typically the highest-energy performances of any comedian's run at Off the Hook. Book in advance.
🎶 Sounds on Strada — Live Music at Mercato📍 Mercato Piazza, 9110 Strada Place, North Naples
🕕 6:00 PM – 8:00 PM | 🎟 Free
Mercato's weekly Saturday live music series in the Piazza. Lawn chairs welcome, no outside coolers. Easy access to dinner and drinks at surrounding restaurants. One of the most reliable free Saturday evenings in Naples.
🗓️ Sunday, September 7
🎙️ Open Mic Night 📍 Check The Oasis (1046 Pine Ridge Rd) and local venues
🕖 Evening | 🎟 Free
Multiple Naples venues run Sunday evening programming including open mic and live entertainment. Check individual venues for September schedules.
🗓️ Monday, September 8
🎷 Jebry & Friends Jazz Jam📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples
🕕 6:00 PM – 9:00 PM | 🎟 Free | dogtoothnaples.com
Every Monday without exception — the most consistent live jazz experience in Naples. Jebry & Friends Jazz Jam runs year-round with rotating guest musicians joining the house ensemble. No cover, no reservation needed.
🗓️ Tuesday, September 9
🎯 Spotlight Trivia Night — The Oasis Naples📍 The Oasis, 1046 Pine Ridge Road, Naples
🕖 7:30 PM | 🎟 Free to play | theorasisnaples.com | 239-649-0800
Spotlight Trivia runs every Tuesday at 7:30 PM at The Oasis. A fun, low-key option for teams of two to six — no cover, full menu and bar available. A good way to ease into the week.
🔁 Running All Week
🍽️ Sizzle Dining 2026
All September | 140+ restaurants | sizzledining.org | Book directly with restaurants
🎨 Latin Modernism Exhibition — Norris Center
Through September 30 | Free | 755 8th Avenue South, Naples
🌿 Naples Botanical Garden
Daily 8 AM – 5 PM | 4820 Bayshore Drive | naplesgarden.org | Adults $27, Children free
