What's Happening in Naples This Week: July 23–29, 2026

A strong week in Naples with something on every night. TJ Miller headlines Off the Hook for four nights. Les Misérables closes its run at the Naples Players on Sunday — final chance to catch it. The Naples Jazz Society plays a free concert Saturday afternoon. Art After Hours at Artis-Naples opens the Baker Museum free on Wednesday evening. And Dogtooth has live music literally every single night this week. Here's everything worth knowing.

😂 TJ Miller — Off the Hook Comedy Club📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕖 7:00 PM | 🎟 $30 general admission + fee | offthehookcomedy.com | 239-389-6901

TJ Miller opens a four-night run at Off the Hook Thursday evening. One of the most recognizable names in stand-up comedy — known for his HBO specials, his role in Silicon Valley, and Deadpool — Miller brings high-energy, unpredictable comedy that has made him a consistent draw on the national circuit. Thursday is the quietest night of the four-show run. Easier parking, easier seating — worth going tonight rather than waiting for the weekend.

🎸 The Collaboration Band — Dogtooth📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕢 6:30 PM – 9:30 PM | 🎟 Free | dogtoothnaples.com | 239-431-7004

Dogtooth opens the week with The Collaboration Band Thursday evening — one of the most versatile live acts in the Naples regular rotation. Covers spanning rock, pop, and classic hits in Dogtooth's casual sports bar setting. No cover, no reservation, just show up.

😂 TJ Miller — Two Shows📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕡 6:30 PM & 8:30 PM | 🎟 $30 + fee | offthehookcomedy.com

Two shows Friday night. If you're doing dinner first, the 8:30 PM set gives you time without rushing. Both shows are the same material, different crowd energy. Friday late-night comedy at Off the Hook is one of the best informal evening options in Naples regardless of who's performing — with TJ Miller in the room, it's one of the strongest entertainment nights of the summer.

⚡ Memphis Lightning — Dogtooth📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕖 7:00 PM – 10:00 PM | 🎟 Free | dogtoothnaples.com

Memphis Lightning brings a blues-rock energy to Dogtooth Friday night. A strong live music option if comedy isn't your thing this evening, or a great second stop after the early Off the Hook show.

🛍️ Third Street South Farmers Market📍 Third Street South, downtown Naples

🕖 7:30 AM – 11:30 AM | 🎟 Free

The 30-year institution runs every Saturday. Fresh produce, baked goods, local vendors, and strong coffee in the heart of Old Naples. The best way to start any Naples Saturday.

🎷 Naples Jazzmasters — Free Concert📍 Norris Community Center, 755 Eighth Avenue South, Naples

🕐 1:00 PM – 3:00 PM | 🎟 Free | thenaplesjazzsociety.com

The Naples Jazz Society hosts its monthly free concert at Norris Community Center Saturday afternoon. The Jazzmasters play from 1 to 3 PM — a two-hour set of live jazz in an intimate community setting that costs absolutely nothing and delivers genuinely high-quality music. This is one of the most underrated recurring events in Naples. Go.

😂 TJ Miller — Two Shows📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕕 6:00 PM & 8:00 PM | 🎟 $30 + fee | offthehookcomedy.com

Two shows Saturday — 6 PM and 8 PM. The 6 PM show gets the dinner crowd. The 8 PM gets the night owls. TJ Miller's Saturday night shows at Off the Hook are reliably the highest-energy performances of any comedian's run. Tickets are going fast — book now.

🎶 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 runs all summer. Lawn chairs welcome, no outside coolers. Easy access to dinner and drinks at the surrounding restaurants. One of the most effortless free Saturday evenings in Naples.

🎭 Les Misérables — Second-to-Last Weekend📍 Kizzie Theater, 701 5th Avenue South, Naples

🕖 7:30 PM | 🎟 From $57.50 | naplesplayers.org | 239-263-7990

Les Misérables closes Sunday. If you haven't been yet, this weekend is genuinely your last opportunity. The Naples Players' 73rd season opener has been one of the most ambitious productions the company has staged — the Tony Award-winning musical centered on Jean Valjean and the French Revolution is not a small undertaking for any theater company. Saturday night at 7:30 PM is the second-to-last performance. Book now.

🎭 Camp Rock Jr.📍 Kizzie Theater, 701 5th Avenue South, Naples

🕑 2:00 PM matinee | 🎟 naplesplayers.org

The Naples Players youth production runs Saturday afternoon at 2 PM alongside Les Misérables. High energy, great young performers — a perfect family Saturday matinee before the evening shows.

🎸 Deb & The Dynamics — Dogtooth📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕖 7:00 PM – 10:00 PM | 🎟 Free | dogtoothnaples.com

Dogtooth closes Saturday night with Deb & The Dynamics — one of the more energetic live acts in the Naples regular music rotation. A strong late option after dinner or the early Off the Hook show.

😂 TJ Miller — Final Show📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach Road #1100, Naples

🕕 6:00 PM | 🎟 $30 + fee | offthehookcomedy.com

Last chance to catch TJ Miller's Naples run. Sunday at 6 PM — the final performance of the four-night engagement. If you missed Thursday through Saturday, this is the one.

🎭 Les Misérables — FINAL PERFORMANCE📍 Kizzie Theater, 701 5th Avenue South, Naples

🕑 2:00 PM | 🎟 From $57.50 | naplesplayers.org

The final curtain call for the Naples Players' Les Misérables. Sunday matinee at 2 PM closes the run that opened June 24. After today, it's gone. If you've been planning to go, today is the day.

🥁 Dogtooth Jam📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕐 1:00 PM – 4:00 PM | 🎟 Free | dogtoothnaples.com

Sunday afternoon Dogtooth Jam — open format, rotating musicians, low-key atmosphere. A perfect Sunday wind-down before the week starts.

🎺 Manhattan Connection — Dogtooth📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕡 6:30 PM – 9:00 PM | 🎟 Free | dogtoothnaples.com

Manhattan Connection plays Dogtooth Sunday evening to close out the weekend. A classic covers band with range — a reliable Sunday night option in Naples year-round.

🎷 Jebry & Friends Jazz Jam — Dogtooth📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕕 6:00 PM – 9:00 PM | 🎟 Free | dogtoothnaples.com

Every Monday at Dogtooth — the most consistent live jazz experience in Naples. Jebry's Jazz Jam runs every single Monday regardless of the season, with rotating guest musicians joining the house ensemble for an open, warm, genuinely musical Monday evening. No cover. No reservation. Just show up.

🎸 Mudbone Blues and Beyond Jam — Dogtooth📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕖 7:00 PM – 10:00 PM | 🎟 Free | dogtoothnaples.com

Tuesday night blues at Dogtooth. Mudbone Blues and Beyond brings a soulful, gritty blues energy to the room that plays particularly well on a Tuesday when you want something real without a big production around it.

🎨 Art After Hours — Artis-Naples / Baker Museum📍 The Baker Museum, Artis-Naples, 5833 Pelican Bay Blvd, Naples

🕕 6:00 PM – 9:00 PM | 🎟 Free admission | artisnaples.org | 239-597-1900

The last Wednesday of every month, Artis-Naples opens The Baker Museum to the public completely free from 6 to 9 PM — with live music by local musicians and concessions at Heidi's Place running alongside the open galleries. July's Art After Hours lands on the 29th. Three hours of free museum access, live music, and one of the best art spaces in Southwest Florida. There is no reason not to go.

🎹 Trivia Night — Dogtooth📍 Dogtooth Sports and Music Bar, 5310 Shirley Street, Naples

🕖 7:00 PM – 9:00 PM | 🎟 Free | dogtoothnaples.com

Dogtooth closes the week with Trivia Night Wednesday evening — a fun, casual Wednesday option for teams of friends or couples looking for something interactive. No cover.

🎭 Camp Rock Jr. — The Naples Players
Various showtimes through the weekend | 701 5th Avenue South | naplesplayers.org

🌿 W.O.N.D.E.R. in the Garden — Naples Botanical Garden
Fri–Mon | 10:00 AM – 12:00 PM | 4820 Bayshore Drive | Included with admission

🎷 Jebry's Jazz Jam
Every Monday | 6–9 PM | Dogtooth, 5310 Shirley Street | Free

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