As summer days wind down, Southwest Florida takes its first steps into the region’s version of fall. In Everglades City, folks gather to celebrate the start of stone crab season with the Blessing of the Stone Crab Fleet. In Fort Myers, Alliance for the Arts debuts its inaugural short film festival with talented local storytellers. And throughout Southwest Florida, more than 90 restaurants embark on this year’s Sizzle Dining experience. Dive headfirst into this month’s events.
Now — Sep. 2
Jimmy Buffet Day At Margaritaville Beach Resort, Fort Myers
Celebrate Labor Day, drink in hand, as you toast to the late king of relaxation. Find plenty of festivities to keep the party going, from music trivia about the singer-songwriter to a dunk tank fundraiser supporting Fort Myers nonprofit Calusa Waterkeepers.
Sept. 5-25
Sizzle Dining (Restaurant Week), Southwest Florida
Test out a new culinary hotspot or revisit an old favorite as more than 50 of the top restaurants across Collier and Lee counties offer special, discounted lunch and dinner menus for three weeks.
Sept. 14
Candlelight: A Tribute to Coldplay on Strings at Naples United Church of Christ, Fort Myers
Immerse yourself in melodic renditions of the British band’s hits played on violin, bass and cello as thousands of flames candles ignite a peaceful ambience throughout the room.
Sept. 19
Summer String Yoga Series at AC Hotel, Naples
Rosemallow Market hosts yogis for a transformative session with The Flow Body instructor Kim Quan. Guests stretch and meditate among glowing candles and atmospheric string music from Naples-based group Jade Strings. Stick around afterward for vendor giveaways, free bubbly and tasty spreads.
Sept. 20
Shorts of the Fort Film Festival at Alliance for the Arts, Fort Myers
Explore the islands, beaches and neighborhoods of Fort Myers at this inaugural short film festival screening Lee County-inspired flicks from local filmmakers. Don’t miss your chance to meet the storytellers and see who takes home the $1,000 “Best of the Fest” prize at the closing awards ceremony.
Sept. 20-29
Island Hopper Songwriter Fest, Lee County
Get up close and personal with today’s stars and musical newcomers at stages from Captiva Island to Cape Coral and Fort Myers at this 10-day songwriting extravaganza. Former American Idol champ Scott McCreery and Grammy Award-nominated Jeffrey Steele—who will play with Gulf Coast Symphony—headline the festival.
Sept. 21
Key Lime & Tropical Fest at Fishermen’s Village, Punta Gorda
Tap into the signature tang of the Sunshine State with themed food and drinks. Groove to live performances from local artists, and swing by stands where vendors showcase their experimental creations.
Sept. 21
Oktoberfest in Bonita Springs
Join Hopsized Brewing’s annual bash, where guests sip steins of German-style beer and cheer on local breweries as they compete in the Brewers Olympic Games. Raffles and giveaways keep spirits high throughout the fest.
Sept. 21-22
Feast of San Januarius off Airport-Pulling Road, Naples
The Naples Italian American Foundation honors the traditions of days past by paying tribute to Saint Januarius in this weekend festival full of rich customs and native fare.
Sept. 25
Cape Coral Paint Night: Moonlight & Cocktail at Stevie Tomato’s, Cape Coral
Transform your dream drink into a stunning work of art as an instructor guides the class in creating a refreshing cocktail set against a night sky backdrop. With each brush stroke, the 16x20-inch canvas transforms into a frame-worthy keepsake.
Sept. 27-29
Chicago The Musical at Broadway Palm Dinner Theatre, Fort Myers
The longest-running Broadway production in America tells the story of Roxie Hart’s infamous rise to fame as she works with a witty lawyer to dodge a conviction for the death of her romantic fling.
Sept. 28
Blessing of the Stone Crab Fleet at Camellia Street Grill, Everglades City
Southwest Floridians commemorate the region’s dedicated fleets at this event to welcome a prosperous stone crab season ahead. Celebrate with live music, arts and crafts and great eats. And, crafty bakers test their merits in the coconut guava cake contest.
Sept. 28
Bonita Springs Pride Festival at Arts Bonita
Hang with the queens, munch on food truck delicacies and savor crafted drinks—including a complimentary beverage. No one leaves empty-handed: Each guest walks away with a Bonita Springs Pride bracelet to commemorate the occasion.
Sept. 28
Fort Myers Oktoberfest Bar Crawl at The Standard Restaurant, Fort Myers
Take a self-guided tour through local pubs and taste Bavarian flavors with German drink specials. Follow the digital bar crawl map and explore different taverns for an unforgettable night.
Sept. 28
Marlon Wayans at Barbara B. Mann Performing Arts Hall, Fort Myers
The White Chicks actor and stand-up comedian takes the stage as part of his Wild Child Tour, guaranteeing a night full of belly-ached laughter and amusement.
Sept. 28 — Oct. 27
Farmer Mike’s 10th Annual Fall Festival & Corn Mazes at Farmer Mike’s U Pick, Bonita Springs and Fort Myers
Pick the perfect pumpkin from the 5-acre patch, saddle up for a hayride and enjoy food and drinks at this annual fest. Brave the alien-invaded haunted corn maze to ring in the spooky season or participate in the returning family-friendly maze designed especially for little ones.