Looking for something fun to do in Southwest Florida this weekend? From live music on Captiva and classic cars in Naples and Marco Island to waterfront festivals, vintage shopping, theater and puppy yoga, there is something happening from Marco Island to Port Charlotte.
Here are some of the best events taking place across Southwest Florida from Friday, September 18, through Sunday, September 20, 2026.
Marco Island
Marco Island Car Cruise
When: Saturday, September 19, from 10:00 a.m. to noon
Where: Marco Lutheran Church, 525 N. Collier Blvd., Marco Island
Admission: Free
Start Saturday morning with coffee and a collection of classic, Corvette and muscle cars at this free weekly community cruise. It is an easygoing stop for car enthusiasts, families or anyone looking for a relaxed way to begin the weekend on Marco Island.
View Marco Island Car Cruise details
Sanibel & Captiva
Island Hopper Songwriter Fest Opening Weekend
When: Opening weekend begins Friday, September 18
Where: Participating venues throughout Captiva Island
Admission: Most performances are free; select special performances may require tickets
The Island Hopper Songwriter Fest returns with live performances at some of Captiva’s best-known restaurants, resorts and waterfront gathering places. Opening-night shows begin as early as 6:30 p.m. at venues including RC Otter’s, ’Tween Waters Inn & Marina and The Green Flash. Check the official schedule to build your own island-hopping music itinerary.
View the Island Hopper festival schedule
Naples
Completely Unchained: A Van Halen Tribute
When: Friday, September 18, at 8:00 p.m.
Where: South Street Grill, Naples
Turn up your Friday night with Completely Unchained, a Van Halen tribute band bringing the sound and energy of the legendary rock group to Naples. Fans can expect a high-energy evening filled with familiar hits.
View Completely Unchained tour details
Cars & Coffee 239
When: Sunday, September 20, from 9:00 to 11:00 a.m.
Where: Mercato, North Naples
Admission: Free for spectators and participating vehicles
Cars & Coffee 239 brings hundreds of privately owned vehicles to Mercato for one of Southwest Florida’s largest informal car gatherings. All makes and models are welcome, and spectators can enjoy coffee, live music and nearby brunch options while exploring the displays.
View Cars & Coffee 239 details
Bonita Springs & Estero
Night Market at The Springs
When: Friday, September 18, from 6:00 to 9:00 p.m.
Where: The Springs at Salt Creek, Estero
Spend Friday evening browsing handmade crafts, art, jewelry, clothing, home décor and specialty products from local makers and small businesses. Locally crafted drinks and food-truck fare add to the laid-back nighttime market atmosphere.
Truck Yeah! Food Truck Rally
When: Saturday, September 19, from 1:00 to 9:00 p.m.
Where: Riptide Brewing Company, 28120 Hunters Ridge Blvd. #1, Bonita Springs
Bring the family or meet up with friends for an afternoon and evening of food-truck favorites and local brews. This recurring third-Saturday rally offers a casual setting for eating, drinking and enjoying the Bonita Springs community.
View Truck Yeah! Food Truck Rally details
5th Annual Oktoberfest Party
When: Saturday and Sunday, September 19–20, from 10:00 a.m. to 6:00 p.m.
Where: Hopsized Brewing Company, Bonita Springs
Celebrate Oktoberfest with German-inspired food, music, trivia, stein-holding competitions, food trucks and special-edition Hopsized brews. It is a festive weekend stop for anyone ready to welcome fall with Bavarian flavor and local craft beer.
View Oktoberfest event details
Fort Myers
Vintage Market Days of South Gulf Coast Florida
When: Friday and Saturday, September 18–19, from 10:00 a.m. to 4:00 p.m.; Sunday, September 20, from 10:00 a.m. to 3:00 p.m.
Where: Lee Civic Center, 11831 Bayshore Road, Fort Myers
Browse an upscale indoor-outdoor market featuring antiques, vintage-inspired pieces, clothing, jewelry, original art, handmade treasures, home décor, outdoor furnishings, plants and specialty foods. Children under 12 are admitted free, and purchased tickets allow re-entry throughout the weekend.
View Vintage Market Days details and tickets
Fort Myers Beach
Pirate Fest
When: Saturday, September 19, from 11:00 a.m. to 5:00 p.m.
Where: Fort Myers Beach waterfront
Break out the pirate gear for a waterfront festival featuring treasure hunts, pirate games, live music, vendors, themed food and drinks, pirate-ship activities and a dock party. It is a playful Saturday outing for families and swashbucklers of all ages.
View Fort Myers Beach Pirate Fest details
Cape Coral
Roald Dahl’s Charlie and the Chocolate Factory
When: Friday, September 18, at 7:00 p.m.; Saturday, September 19, at 7:00 p.m.; and Sunday, September 20, at 3:00 p.m.
Where: Cultural Park Theatre, 528 Cultural Park Blvd., Cape Coral
Step into Willy Wonka’s world as Charlie Bucket and the other golden-ticket winners journey through the mysterious chocolate factory. This stage production offers a family-friendly mix of imagination, music and theatrical fun.
View show information and purchase tickets
Punta Gorda & Port Charlotte
Key Lime & Tropical Fest
When: Saturday, September 19, from noon to 6:00 p.m.
Where: Punta Gorda waterfront
Admission: Free
Enjoy a tropical Saturday along the waterfront with key lime treats, specialty vendors and live island-inspired music. This free festival brings together some of Florida’s favorite flavors in a relaxed outdoor setting.
View Key Lime & Tropical Fest details
Puppy Yoga Benefiting the Animal Welfare League
When: Saturday, September 19, from 9:00 to 10:30 a.m.
Where: Ortiz Event Center, 2685 S. Tamiami Trail, Port Charlotte
Admission: $35 per person; advance registration recommended
Find your balance while adoptable puppies mingle around the mats during a full yoga class led by an instructor from The Yoga Sanctuary. All skill levels are welcome, participants should bring their own mats, and proceeds support animals in the care of the Animal Welfare League of Charlotte County.
View Puppy Yoga details and registration information
Make the Most of Your Southwest Florida Weekend
Whether you are searching for live music, family-friendly activities, food festivals, theater, markets or car shows, this weekend offers plenty of reasons to get out and explore Southwest Florida. Choose an event close to home or plan a day trip to experience another corner of the Gulf Coast.
Event information can change because of weather, capacity or organizer updates. Before heading out, use the event links above to confirm the latest times, locations, admission details and ticket availability.
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