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What to Do in Southwest Florida in September & October 2019

Aug 26, 2019 05:03PM ● By Patricia Letakis
The Island Hopper Songwriter Fest is held in Fort Myers, Captiva Island and Fort Myers Beach September 20-29.

Events You Don't Want to Miss - September & October 2019

Sept. 6 Seinfeld Live, Fort Myers

Jerry Seinfeld, America’s premier comedian, brings his stand-up routine to the Barbara B. Mann Performing Arts Hall in Fort Myers. The TV series Seinfeld, which he created with Larry David and then starred in, became one of the most popular sitcoms in American television. Seinfeld’s been hailed for his uncanny ability to joke about the little things that relate to audiences everywhere.

Sept. 14 SummerJazz on the Gulf, Naples

One of the most popular concert series in Southwest Florida, SummerJazz on the Gulf takes over the Watkins Lawn at the Naples Beach Hotel & Golf Club, offering music lovers views of the glistening Gulf of Mexico and glorious sunsets. The final concert on Sept. 17 features Ari & The Alibis. Infusing funk, soul, jazz, rock and samba with blues, the band ignites the crowd. The concert is free; bring your blanket or lawn chair.

Sept. 19 Tapa Hop, Fort Myers Beach

Hop on the trolley with like-minded foodies to sample tapas along Fort Myers Beach. Seven restaurants have prepared their tastiest tapas for an evening of fun and food. It starts at the South Beach Grille at 3:30 p.m.; the Tapa Hop continues all evening long with stops at restaurants until 10 p.m. Both trolley transportation and the samplings are included in the ticket. 239-454-7500

Sept. 19 Disturbed Evolution Tour, Estero

The American heavy metal band Disturbed rocks the Hertz Arena in Estero with its bold amplified sound as it brings its Evolution Tour to Southwest Florida. Expect to hear songs like “Are You Ready” and “The Sound of Silence” performed by the group. The show’s special guest is the goth-rock band In This Moment, known for its metalcore roots.

Sept. 20 Julio Iglesias, Estero

One of the most celebrated performers in Spanish and Latin music history, Julio Iglesias boasts more than 300 million records sold in 14 languages and 2,600 gold and platinum albums. At 75, the crooner hasn’t lost his smooth romantic appeal when he sings “Abrázame,” “Por el Amor de Una Mujer,” “Quiereme Mucho” and other love songs. See him at the Hertz Arena in Estero.

Sept. 20-29 Island Hopper Songwriter Fest, Captiva, Fort Myers & Fort Myers Beach

Nationally acclaimed singer-songwriters perform in Fort Myers, Fort Myers Beach and Captiva Island during the Island Hopper Songwriter Fest. The 10-day festival includes 150-plus free shows at some 20 intimate venues, pool parties, private house parties and a workshop featuring the country’s top songwriters. Among this year’s lineup is Brandon Kinney, whose songs have been produced by country music stars Jason Aldean, Cole Swindell, Luke Bryan, Jon Pardi and Justin Moore. Other top writers appearing include Aaron Barker, who wrote George Strait’s 1990 super hit “Love Without End, Amen,” and Dylan Altman, who’s credited with “Barefoot Blue Jean Night” recorded by Florida’s native son Jake Owen.

Sept. 21 Terry Sylvester of the Hollies, Bonita Springs

Enjoy an evening with the British musician Terry Sylvester as he shares highlights from his career with the Hollies and the Escorts during his performance at the Centers for the Arts Bonita Springs. Sylvester performs his hit songs from the ’60s and ’70s “He Ain’t Heavy, He’s My Brother” and “Long Cool Woman in a Black Dress.”

Sept. 24-Nov. 10 Always…Patsy Cline, Fort Myers

Kicking off the season at Florida Repertory Theatre is the stage show Always…Patsy Cline. It celebrates the life of the iconic country singer from her early performances in Texas honky-tonks to her sell-out concerts at the Grand Ole Opry. Patsy Cline earned a place in the world of country music and American culture. The musical tribute features her most famous songs, “Crazy” and “I Fall to Pieces.” 

Sept. 28 Blessing of the Stone Crab Fleet, Everglades City

Preparing for stone crab season, fishermen gather at the Rod & Gun Club in Everglades City to have their vessels blessed by local pastors. The opening ceremony starts at 10:30 a.m. The event also includes arts and crafts booths, live music, a raffle and bake sale, as well as the popular coconut guava cake contest. Kids enjoy face painting, and frog-jumping and stone crab art competitions. 239-695-2905

Oct. 3-Nov. 16 Finding Neverland, Fort Myers

Based on the film Finding Neverland, this musical production tells the true story behind the creation of the fairy-tale character Peter Pan. Playwright J.M. Barrie found inspiration for the free-spirited boy, who refused to grow up, in the make-believe adventures of a widow’s four young sons. It was the boys’ imaginations that fueled Barrie’s creativity, eventually resulting in a play that dazzled London theatergoers in 1904. The magic continues with Finding Neverland at the Broadway Palm Dinner Theatre in Fort Myers. 

Oct. 10-12 Roar Offshore Races, Fort Myers Beach

The American Power Boat Association National Championship wraps up in Fort Myers Beach, the last stop for the inaugural season of this racing series. Come out and see the Miss GEICO offshore racing team compete against Australia, Norway, Sweden and other countries. The freshly painted and rebuilt 47-foot-long Miss GEICO sports a pair of 1,100 horsepower engines and can reach top speeds of more than 160 mph. She competes in Class One, which is comprised of the biggest and fastest race boats. Driver James Sheppard and throttleman Steve Curtis have been unbeatable for the past two seasons and are aiming for a three-peat.

Oct. 11-31 Lakes Regional Park Fall Festival, Fort Myers

Celebrate the season with traditional autumn fanfare. Lakes Regional Park turns into a pumpkin patch, where you can find the perfect pumpkin to take home and carve into a jack-o’-lantern. Thanks to a scarecrow competition, the grounds are dotted with spooky creations in all sizes and artistic styles. Youngsters can ride the Halloween Express, a train decorated for the holiday, and the whole family can enjoy a hayride at the Fort Myers park.

Oct. 18-20, 25-27 Munich in Cape Coral

Everybody loves Oktoberfest, and Cape Coral knows how to throw the biggest German bash, which runs for two consecutive weekends. Attendees find an outdoor biergarten and festival tent with three stages for bands that come directly from Germany, plus two dance floors. Homemade-style food includes: schnitzel, sauerbraten, dumplings, red cabbage, German potato salad, bratwurst, bauernwurst, pretzels and potato pancakes. Grab a stein and sample imported German bier, along with German wines and spirits. Held at the German-American Social Club, the event also includes a carnival area with rides and games for kids.

Oct. 20 “Ding” Darling Day, Sanibel Island

The “Ding” Darling National Wildlife Refuge on Sanibel Island celebrates the birthday of its namesake Jay N. “Ding” Darling, who was the father of the Federal Duck Stamp program and a Pulitzer Prize-winning cartoonist, on “Ding” Darling Day. Bring the family out for free eco-activities, from refuge tram tours and wildlife presentations to archery clinics and yoga sessions. The artistically inclined can partake in origami, craft and nature sketching classes. Tarpon Bay Explorers offers free stand-up paddleboarding clinics, and discounted boating excursions and rental kayaks.

Oct. 24-27 Naples International Film Festival

Now in its 11th year, the Naples International Film Festival (NIFF) just keeps getting bigger and better. The four-day event offers more than 60 screenings at the Silverspot Cinema. Domestic and international narrative, documentary and short films from established and emerging filmmakers are presented. With $25,000 in cash prizes up for grabs, filmmakers can compete in juried competitions as well as audience awards. NIFF is now part of Artis—Naples, and its Cultural Campus serves as the venue for the opening night film and party (Oct. 24) and the closing night awards ceremony (Oct. 27), which features Jack Everly conducting the Naples Philharmonic in John Williams’ triumphant score to the classic Steven Spielberg film Raiders of the Lost Ark.

Oct. 25-26 Psycho With A Live Orchestra, Punta Gorda & Fort Myers

The Southwest Florida Symphony puts the force of live music behind an Alfred Hitchcock thriller. As if Psycho, the 1960 psychological horror film, isn’t suspenseful enough, the orchestra makes watching the movie an even more intense experience. See the film and hear the musicians at the Charlotte Performing Arts Center in Punta Gorda on Oct. 25 and at the Barbara B. Mann Performing Arts Hall in Fort Myers on Oct. 26.

Oct. 31 Fall Family Candy and Costume Festival, Sanibel Island

Dress in your favorite Halloween costume and head to The Community House on Sanibel Island for some festive fall fun. The evening event (5-7 p.m.) is an opportunity to mingle with neighbors, play games and eat lots of candy! Admission is a bag or two of candy per family.

Oct. 25-27 Stone Crab Festival, Naples

To kick off the stone crab season that runs from October to May, Naples holds its annual Stone Crab Festival at venues on the Old Naples Waterfront—Tin City, Bayfront, Port of Naples Marina and other locations. Plenty of fresh stone crab claws are cracked, served and devoured. Folks enjoy live music the entire weekend. 

Oct. 19 and 26 Florida Everblades, Estero

The Florida Everblades kick off their home games for the 2019-2020 hockey season in October. They take on the Norfolk Admirals on Oct. 19 and challenge the Orlando Solar Bears on Oct. 26. You don’t have to be a diehard ice hockey fan to enjoy a rousing game of non-stop super-speed action played at the Hertz Arena in Estero.

Nov. 1-3 Florida International Air Show, Punta Gorda

Make plans to attend the Florida International Air Show at the Punta Gorda Airport. The main attraction is a performance by the United States Air Force Thunderbirds, an elite air demonstration squadron, on Saturday and Sunday afternoons. Air shows throughout the weekend include the SOCOM Para Jump Team, Matt Younkin’s Twin Beech 18 and others. Displays of aircrafts and a finale fireworks show round out the event.