September 2026 Events in SWFL You Won't Want to Miss
September 2026 Events in SWFL You Won't Want to Miss
From roaring powerboats on the Gulf to Nashville songwriters in an intimate Cape Coral courtyard, September is lighting up the SWFL events calendar. Here's your guide to what's happening — and why this region never runs out of reasons to love calling it home.
One of our favorite parts of living and working in Southwest Florida is the sheer variety of things to do here, all year long. Whether you're already a local, considering relocating, or just visiting to see if this could be your next home base, here are five events worth marking on your calendar this September.
Roar Offshore Powerboat Races
Fort Myers Beach kicks off a busy September with three days of world-class powerboat racing, watching some of the fastest offshore boats in the country roar past the shoreline. Roar Offshore has become a signature SWFL tradition, drawing racing teams and spectators from across the country to the beach and surrounding waterfront businesses.
It's also part of a bigger story: local business owners say events like this are a major part of Fort Myers Beach's continued comeback, bringing energy, visitors, and a boost to island restaurants and shops during the tail end of summer.
View Event Details →Island Hopper Songwriter Fest — Krystal King at Gather
Southwest Florida's longest-running music festival returns for 10 days (September 18–27) of pop-up performances across Captiva Island, Fort Myers, Fort Myers Beach, and Cape Coral. One stop we're especially excited about: singer-songwriter Krystal King performs in the round with Lilly MacPhee at Gather in Cape Coral, bringing an intimate, storytelling-style show straight to our own backyard.
This year's festival lineup features Nashville names like Edwin McCain, Alexandra Kay, LOCASH, and Michael Ray, with performances happening in bars, restaurants, and resorts throughout the week. If you love live music in a laid-back setting, this is the SWFL event of the season.
View Krystal King at Gather → Full Festival Schedule →Glitter & Gold: A Celebration of Broadway
Right here in Cape Coral, The Belle Theatre brings Broadway favorites to the stage with "Glitter & Gold," a musical revue celebrating the glitz and heart of the Great White Way. It's a great date-night or girls'-night option that proves you don't have to leave Southwest Florida for a top-tier live performance.
The Belle Theatre is located at 2708 Santa Barbara Blvd., Suite 135, Cape Coral. Tickets and showtimes are available online or by calling 239-323-5533.
View Event Details →Music Under the Stars
One of the most unique live music settings in Southwest Florida: Blues Music Award-winning songwriter Doug MacLeod performs his soulful, acoustic blues underneath the star-filled dome of Calusa Nature Center's planetarium. Presented in partnership with the Americana Community Music Association, it's an intimate, one-of-a-kind evening that regulars keep coming back for all season long.
Calusa Nature Center & Planetarium is located at 3450 Ortiz Ave, Fort Myers.
View Event Details →Sizzle Dining
Now celebrating its 10th year, Sizzle Dining brings discounted, chef-curated menus to 140+ restaurants from Cape Coral to Marco Island all month long — two-course breakfasts and lunches from $19, and three-course dinners from $29. For every meal sold, participating restaurants donate $1 to Blessings in a Backpack Southwest Florida, which provides weekend meals to local food-insecure elementary students.
It's a great, low-key excuse to try somewhere new while supporting local kids and local restaurateurs at the same time.
View Event Details →Why This Matters If You're Buying or Selling in SWFL
Events like these aren't just fun weekend plans — they're a snapshot of what makes Cape Coral, Fort Myers, Naples, Bonita Springs, and Estero such special places to put down roots. A community with this much energy, culture, and connection is exactly what so many buyers and relocating families are looking for. If you're thinking about making Southwest Florida home, we'd love to show you around — neighborhoods and all.
Ready to Explore Southwest Florida?
Whether you're buying, selling, or just curious about the market, Integrity 1st Group is here to help.
Visit Our Website Call (239) 471-2550integrity1stgroup@gmail.com | 615 Cape Coral Pkwy W, Suite 105, Cape Coral, FL 33914
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