Published: November 5, 2026
Last reviewed: November 5, 2026
Looking for things to do in Southwest Florida this weekend? From the Florida International Air Show and Taste of Mercato to island races, theater, car shows and waterfront entertainment, there are events happening from Marco Island to Port Charlotte from Friday, November 6 through Sunday, November 8, 2026.
Southwest Florida Weekend Events at a Glance
Area | Event | Date and time |
|---|---|---|
Marco Island | Jerry Adams Chili Cook-off | Saturday, 11 a.m.–3 p.m. |
Marco Island | Packing Up Polly | Friday, 7:30 p.m.; Saturday and Sunday, 3 p.m. |
Sanibel | JOG N JAM 10K, 5K & Kids Fun Run | Saturday, 7:30–10 a.m. |
Sanibel | Saturday Vinyasa & Tea | Saturday, 9–10 a.m. |
Captiva | Live Music at ’Tween Waters | Saturday and Sunday |
Naples | Naples Airport Runway 5K & 10K | Saturday, 7:30 a.m. |
Naples | Taste of Mercato | Saturday, 5–8 p.m. |
Naples | The World Goes ’Round | Performances all weekend |
Bonita Springs | Silent Disco Run & Rave | Friday, 4:30–9 p.m. |
Estero | Breakthrough T1D Walk | Saturday, registration 7:30 a.m. |
Estero | Backyard Social Car Show | Sunday, 10 a.m. |
Fort Myers Beach | Illuminations Parade | Saturday, 5:30–8 p.m. |
Fort Myers Beach | Bayside Park Concert: The Echo | Sunday, 4–7 p.m. |
Fort Myers | “Sandman’s Wake” Gallery Opening | Friday, 6 p.m. |
Fort Myers | The Fast & the Furriest 5K | Saturday, 8 a.m. |
Cape Coral | Roger Dean Chevrolet Car Show | Saturday, 1 p.m. |
Cape Coral | Comedy Night with Mike Rivera | Saturday, 7 p.m. |
Punta Gorda | Florida International Air Show | Saturday and Sunday, gates 9 a.m. |
Port Charlotte | Sunseeker Jazz Fest: Food & Wine | Friday and Saturday |
Marco Island Events
14th Annual Jerry Adams Chili Cook-off
When: Saturday, November 7, 11 a.m.–3 p.m.
Where: The Esplanade Shoppes, 760 N. Collier Blvd., Marco Island
Admission: $25; children 12 and younger are free
Sample recipes from chili teams across Marco Island during this annual fundraiser for the Marco Island Fire Rescue Foundation. Admission includes the opportunity to taste the entries and vote for a favorite.
View the Chili Cook-off details
Packing Up Polly
When: Friday, November 6 at 7:30 p.m.; Saturday and Sunday at 3 p.m.
Where: Arts Center Theatre, 1089 N. Collier Blvd., Suite 432, Marco Island
Admission: $35 for members; $40 for non-members; check availability before going
Leslie Kimbell’s comedy follows four longtime friends who reunite in Savannah to clear out the cluttered home of a gospel-singing hoarder. The production continues through November 22, but the theater’s ticket page currently shows several performances as sold out, so confirm availability.
View show and ticket information
Sanibel and Captiva Events
JOG N JAM 10K, 5K & Kids Fun Run
When: Saturday, November 7, 7:30–10 a.m.
Where: Sanibel Community House, 2173 Periwinkle Way, Sanibel
Admission: Tiered race registration; price increases closer to race day
Run or walk a scenic island course while supporting FISH of SanCap. The morning includes 10K and 5K distances plus a Kids Fun Run, making it a strong choice for active families.
Saturday Vinyasa & Tea
When: Saturday, November 7, 9–10 a.m.
Where: The Treehouse, 1101 Periwinkle Way, Suite 106, Sanibel
Admission: $25 drop-in
Begin Saturday with an all-levels vinyasa flow followed by locally sourced organic tea in a relaxed island setting.
Live Music at ’Tween Waters
When: Saturday, November 7, 1–5 p.m.; Sunday, November 8, 7–10 p.m.
Where: ’Tween Waters Island Resort & Spa, 15951 Captiva Drive, Captiva
Admission: Confirm any venue or dining requirements
Tad Felling performs beside the Oasis Pool Saturday afternoon, followed by The Gatlins at the Shipyard Restaurant Sunday evening. Food and drinks are available at the resort.
View the ’Tween Waters events calendar
Naples Events
Naples Airport Runway 5K & 10K
When: Saturday, November 7, 7:30 a.m.
Where: Naples Airport North Road Terminal, 500 Terminal Drive, Naples
Admission: Standard registration is $45 for the 5K and $55 for the 10K through November 6; race-day pricing is $50 and $60 if space remains
This unique race gives runners and walkers 90 minutes on Runway 32 at Naples Airport. Registration is limited to 600 participants. Dogs and strollers are not permitted on the runway.
View official race information
Taste of Mercato
When: Saturday, November 7, 5–8 p.m.
Where: The Piazza at Mercato, 9110 Strada Place, Naples
Admission: $75 per person
Sample signature bites and seasonal sips from Mercato restaurants while enjoying live entertainment. Proceeds benefit Guadalupe Center programs serving students in Immokalee.
The World Goes ’Round
When: Performances all weekend; check the box office for exact showtimes
Where: Gulfshore Playhouse, 100 Goodlette-Frank Road S., Naples
Admission: Ticketed
The Struthers Studio becomes an intimate jazz club for this musical revue featuring songs by John Kander and Fred Ebb, the award-winning team behind Cabaret and Chicago. The production runs through November 22.
Bonita Springs and Estero Events
Silent Disco Run & Rave
When: Friday, November 6, 4:30–9 p.m.
Where: The Shop, 10979 K-Nine Drive, Bonita Springs
Admission: Check the organizer’s listing
This alcohol-free festival combines a group run led by a mobile DJ with a silent disco, wellness-focused activities and a sober social atmosphere.
Breakthrough T1D Walk
When: Saturday, November 7; registration opens at 7:30 a.m. and the walk begins at 9 a.m.
Where: Miromar Outlets, 10801 Corkscrew Road, Estero
Admission: Fundraising event; registration requested
Walk with families, supporters and community teams raising money for type 1 diabetes research and advocacy.
View the official Southwest Florida T1D event page
Backyard Social Car Show
When: Sunday, November 8, 10 a.m.
Where: Backyard Social, 16371 Corporate Commerce Way, Estero
Admission: Confirm with the organizer
All makes and models are welcome at this casual Sunday-morning car gathering in Estero.
Fort Myers Beach Events
Illuminations Parade
When: Saturday, November 7, 5:30–8 p.m.
Where: Begins near Sandy Bottoms, 2301 Estero Blvd., and travels north to Bayside Veterans Park
Admission: Free to watch
Fort Myers Beach lights up with glowing floats, lanterns, illuminated costumes and island spirit. The family-friendly walking parade begins around dusk and is ADA accessible.
View official parade information
Bayside Park Concert: The Echo
When: Sunday, November 8, 4–7 p.m.
Where: Bayside Park, 645 Old San Carlos Blvd., Fort Myers Beach
Admission: Free
Bring a lawn chair for an outdoor Sunday concert beside the bay. The event is weather permitting, and outside food and beverages are not allowed.
View the Bayside Park concert series
Live Music at Margaritaville Beach Resort
When: Friday and Saturday, 7–10 p.m.; Sunday, 5–8 p.m.
Where: Margaritaville Beach Resort, 251 Crescent St., Fort Myers Beach
Admission: Check individual venue requirements
The resort’s weekend lineup includes Madison Morris, TC and the Troublemakers, Briz and Lady, and Nathan Tata across three evenings.
View the Margaritaville calendar
Live Music at Doc Ford’s
When: Friday, 6–9 p.m.; Saturday and Sunday, 1–4 p.m. and 5:30–8:30 p.m.
Where: Doc Ford’s Rum Bar & Grille, 708 Fishermans Wharf, Fort Myers Beach
Admission: Restaurant seating and availability may apply
Enjoy waterfront music on Matanzas Pass throughout the weekend, with GMB, Steve McDougall, Crossroads, Kelly Neff and Derek of GMB scheduled to perform.
View the Doc Ford’s live music schedule
Fort Myers Events
“Sandman’s Wake” Gallery Opening
When: Friday, November 6, 6 p.m.
Where: Sidney & Berne Davis Art Center, 2301 First St., Fort Myers
Admission: Confirm with the venue
Two exhibitions open during the downtown Fort Myers Art Walk: Jason Sanders’ surreal “Sandman’s Wake” and Ilyas Kirkan’s “Creation Is a Form of Rebellion.”
View the gallery-opening listing
The Fast & the Furriest 5K
When: Saturday, November 7, 8 a.m.
Where: Edison Mall, 4125 Cleveland Ave., Fort Myers
Admission: Race registration required
This pet-friendly 5K invites runners and walkers to bring a four-legged companion for a fun morning in Fort Myers.
Cape Coral Events
Roger Dean Chevrolet Car Show
When: Saturday, November 7, 1 p.m.
Where: Roger Dean Chevrolet, 101 SW Pine Island Road, Cape Coral
Admission: Confirm with the organizer
See vehicles ranging from classic favorites to modern builds, with trophies awarded during the afternoon.
Comedy Night with Mike Rivera
When: Saturday, November 7, 7 p.m.
Where: Cultural Park Theatre, 528 Cultural Park Blvd., Cape Coral
Admission: Ticketed; purchase only through the theater’s official site
Comedian, teacher and father Mike Rivera brings his clean, high-energy stand-up to Cultural Park Theatre. The venue warns that tickets from unauthorized third-party resellers will not be accepted.
Buy tickets from Cultural Park Theatre
Punta Gorda and Port Charlotte Events
Florida International Air Show
When: Saturday, November 7 and Sunday, November 8; gates open at 9 a.m. and opening ceremonies begin at 11:30 a.m.
Where: Punta Gorda Airport, Punta Gorda
Admission: Ticketed; free parking; rain or shine
Southwest Florida’s major aviation weekend includes aerial performances by the A-4 and MiG-17, Kevin Coleman, Franklin’s Flying Circus and The Chuters skydiving team. Families can also explore the STEM Pavilion, Kids Zone and static aircraft displays. Performer times are approximate and may change.
View the official air show schedule and tickets
Sunseeker Resort Jazz Fest: Food & Wine Weekend
When: Wine Around on Friday, November 6, 6–10 p.m.; Serenade & Supper on Saturday, November 7, 5–9:30 p.m.
Where: Sunseeker Resort, 5500 Sunseeker Way, Port Charlotte
Admission: Friday is free to attend with food and drinks available à la carte; Saturday tickets start at $149 plus tax
Friday offers live jazz and food-and-wine pairings throughout the resort. Saturday’s formal gala features a four-course dinner, paired wines and a headline performance by Danny Sinoff with the Stardust Memories Big Band.
View the official Jazz Fest schedule
Frequently Asked Questions
What are the best family-friendly events in Southwest Florida this weekend?
Strong family choices include the JOG N JAM Kids Fun Run on Sanibel, the free Illuminations Parade on Fort Myers Beach, the Breakthrough T1D Walk in Estero and the Florida International Air Show’s Kids Zone and STEM Pavilion.
What free events are happening in Southwest Florida November 6–8?
The Illuminations Parade and Bayside Park concert are free. Sunseeker’s Friday Wine Around is free to enter, although food and drinks are purchased separately. Some car shows and gallery events may also be free, but confirm before going.
What is the biggest event in Southwest Florida this weekend?
The Florida International Air Show at Punta Gorda Airport is one of the weekend’s largest regional events, with two full days of aerial entertainment, ground displays and family attractions.
Are there outdoor events this weekend?
Yes. Options include several races and walks, car shows, the Fort Myers Beach parade and concert, the Marco Island chili cook-off and the Punta Gorda air show. Check the forecast and organizer updates before leaving.
Where can I find things to do near Naples and Fort Myers?
Naples offers the Runway 5K & 10K, Taste of Mercato and Gulfshore Playhouse. The Fort Myers area has Art Walk exhibitions, a pet-friendly 5K, waterfront concerts, the Illuminations Parade and several live-music schedules.
Explore Southwest Florida Beyond the Weekend
Weekend events are one of the many reasons people love living in Southwest Florida. To explore communities and homes from Marco Island through Naples, Bonita Springs, Fort Myers, the islands, Cape Coral and Punta Gorda, visit John R. Wood Christie’s International Real Estate.
Recommended Blog Tags
Southwest Florida Events, Things to Do in Southwest Florida, SWFL Weekend Events, Naples Events, Fort Myers Events, Marco Island Events, Sanibel Events, Fort Myers Beach Events, Cape Coral Events, Punta Gorda Events, Family Events in Southwest Florida, November Events in Florida
Event dates, times, prices, performers and availability can change. Confirm final details with the organizer before attending.
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