Visitors' Guide/ Itinerary

Top Events from September to May

From Broadway plays to food festivals to interactive exhibits, this year brings a slate of must-see happenings in Collier, Lee and Charlotte Counties.

BY August 31, 2022
Ballet dancer
Classical music and contemporary dance merge in BalletX’s performance alongside Naples Philharmonic at Artis—Naples in November. (Getty Image)

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Check the organizations’ websites for the latest information.

September 2022


Through Nov. 27

Helen Frankenthaler: Late Works, 1990-2003

The Baker Museum is among the first in the country to get this unique collection that looks at the later years of the Abstract Expressionist pioneer, known for her experimentation with materials and techniques.


Through Dec. 10

The Exquisite Moving Corpse

In the 1920s, surrealist artists developed “exquisite corpses,” collaborative figurative works done on passed-around pieces of paper. During the pandemic, 60 artists modernized the idea, with each creating a 1-minute clip that responds to the last frame. The result is this hour-long weird and beautiful tour de force, with renowned conceptual artists including Jack Massing, William Wegman, Chip Lord and Kristin Lucas.


Through Nov. 2023


Wander through intricately twisted structures made by North Carolina-based environmental artist Patrick Dougherty, using 30,000 pounds of willow saplings at Naples Botanical Garden.


Sep. 8-28

Sizzle Dining

The semi-annual event offers two- and three-course prix fixe menus at dozens of the top restaurants across Lee and Collier counties (Osteria Tulia, Campiello, Bleu Provence and A Table Apart all participate), with a portion of the proceeds benefitting food insecurity for elementary school children.


Sep. 13, Oct. 30, Nov. 21, Dec. 15

Rockin’ on the River

The new Caloosa Sound Amphitheater in Downtown Fort Myers kicks off its debut season with a free concert series along the Caloosahatchee River starring English rock band The Fixx; ’70s soft rock group Pablo Cruise; country singer Lorrie Morgan and swinging jazz emsemble Big Bad Voodoo Daddy.


Sep. 16

The Play that Goes Wrong

In its Southwest Florida debut, this award-winning comedy shows director Annette Trossbach’s propensity for breaking the mold. The play within a play draws from Sherlock Holmes’ classic whodunnit and Monty Python’s absurd humor, as a drama student produces a murder mystery on a low budget.


Sep. 16-25

Eighth Annual Island Hopper Songwriter Fest

Discover the lyrical talent local and national songwriters and musicians as they perform at intimate venues on Fort Myers Beach and Sanibel.


Sep. 22

Earth, Wind & Fire

With more than 50 years of performing together, the nine-time, Grammy Award-winning band always brings down the house with groovy hits like “September” at Fort Myers’ Barbara B. Mann Performing Arts Hall.


Sep. 23-24

Jim Gaffigan: The Fun Tour

The Emmy Award-winning comedian and actor, known for his clean comedy, brings his hilarious observations on everyman, everyday issues (and lots of food jokes) to Barbara B. Mann.


Sep. 29

Luke Bryan: Raised up Right Tour

The best-selling country artist and American Idol judge performs in Estero with double-platinum artist Mitchell Tenpenny and Country Music Awards winner Riley Green.


October 2022


Oct. 5

Lady A: Request Line Tour

The five-time, Grammy Award-winning country band performs at Barbara B. Mann Performing Arts Hall, with opening act Dave Barnes, the songwriter behind hits like Blake Shelton’s “God Gave Me You.”


Oct. 14

Trevor Noah: Back to Abnormal World Tour

Expect plenty of political satire and a whole lot of sarcasm from The Daily Show host—one of the most astute comedians on the scene—performs at Hertz Arena.


Oct. 15

Pitbull: Can’t Stop Us Now Tour

Mr. Worldwide, the Miami-born, Latin hip-hop artist, headlines with the Australian rapper behind “Fancy,” Iggy Azalea.


Oct. 15

The Paradise Coast Wine & Food Experience

Some of the brightest stars in Naples’ culinary scene converge at Cambier Park for tastings and demos, with praised local restaurants like 21 Spices by Chef Asif and Sea Salt represented.


Oct. 21-23

29th RedSnook Catch & Release Charity Fishing Tournament

The weekend-long competition supports the Conservancy of Southwest Florida’s mission to fight for clean waterways, with launch sites from Naples, Goodland and Chokoloskee. Kick-off with an outdoor happy hour celebration at Naples’ Florida Sports Park on Friday.


Oct. 27-30

14th Annual Naples International Film Festival

Regularly touted as one of the best film festivals in the region, Artis—Naples’ NIFF brings buzzy, thought-provoking documentaries, shorts and narratives, with an emphasis on sparking dialogue and showcasing diverse perspectives.


Oct. 28-30

13th Annual Naples Stone Crab Festival

The live music by local favorites like Matty Jollie and a slate of arts vendors are the icing on the cake for this bountiful celebration of our regional delicacy.


November 2022


Nov. 1-26

Mally Khorasantchi at Harmon Meek

The internationally recognized, local artist showcases her large-scale expressionist works at the iconic downtown Naples gallery.


Nov. 6-7

WINK’s Taste of the Town

Food trucks touting barbecue, seafood and international eats fill Fort Myers’ Centennial Park for this weekend-long celebration, with live music and family-friendly activities.


Nov. 10


Contemporary ballet and classical music coalesce when the world-touring BalletX dances to tunes from Naples Philharmonic at Artis—Naples.


Nov. 10

Reba: Live in Concert

The Queen of County has been hard at work lately, releasing a new album, producing and starring in a Lifetime flick, and now, blessing us with her musical chops when she performs in Estero.


Nov. 10-13

50th Annual Fort Myers Boat Show

Boat lovers are sure to find their new ride—and engines and boat lifts and fishing gear—when more than 500 boats and hundreds more aquatic accessories go on display along the Caloosahatchee River in downtown Fort Myers.


Nov. 12

Kevin Hart: Reality Check Tour

His movies, like Get Hard and Ride Along, made him famous, but it’s Kevin Hart’s stand-up that showcase what he does best: make you laugh with his self-deprecating wit.


Nov. 12-13

4th Annual WolfStock Festival

Shy Wolf Sanctuary Education & Experience Center in Naples hosts this fundraising beer festival to benefit its resident rescued wolves. Local brewers pour their latest releases and 12-year-old musical prodigy Champ Jaxon (who’s been on The Ellen DeGeneres Show) performs.


Nov. 12 – Dec. 4

Steel Magnolias

Inspired by the Oscar Award-winning film, this play follows six, quick-witted women in the South when tragedy strikes.


Nov. 12 – Feb. 12

M.C. Escher: Reality & Illusion at Naples Art

More than 100 works showcase the fantastical genius of the artist best known for his mind-bending sketches and tessellations.


Nov. 23 – Dec. 18

A Christmas Carol The Musical

The Naples Players’ rendition of Charles Dickens’ famed Ebenezer Scrooge tale has become as much of a tradition as anything else you’ll do this holiday season; don’t miss it.


Nov. 25 – Dec. 23, Dec. 26-30 & Jan. 1

Johnsonville Night Lights in the Garden

Thanks to the creative illuminations, blooming gardens, festive food and drink stations and lively roaming entertainment, Naples Botanical Garden’s holiday experience sells out many of its dates; get tickets early.


Nov. 25 – Dec. 30

Holiday Nights at the Edison & Ford Winter Estates

Another ’tis-the-season tradition in Southwest Florida, the illuminated grounds at the historic estates dazzle with thousands of lights, historically accurate decorations and live music some nights.


Nov. 27

30th Anniversary Tour of NUTCRACKER Magic of Christmas Ballet

The Moscow Ballet’s epic production of the Nutcracker comes to Barbara B. Mann. In solidarity with Ukraine, the ballet company renamed its show this year and is donating part of the proceeds to relief efforts.


December 2022


Dec. 3

33rd Annual Fort Myers Beach Christmas Boat Parade

Boats are decked with lights and Florida-centric Christmas decor for an illuminated cruise down the back bay, starting at Salty Sam’s Marina. Watch from Bayfront Park or one of the nearby waterfront restaurants.


Dec. 8

Frankie Valli & the Four Seasons: Greatest Hits Concert

The original Jersey Boy still puts on a killer show with his powerful falsetto and vocal range that shot him to fame in the ’60s. Catch the 88-year-old Frankie and his award-winning band in their return to Barbara B. Mann.


Dec. 10

QBE Shootout, Live Fest

Country star Brad Paisley headlines the musical event for golf legend Greg Norman’s annual charity tournament, which goes on throughout the weekend at Tiburón Golf Club at The Ritz-Carlton Golf Resort.


Dec. 16 – Jan. 15

Freud’s Last Session

Florida Repertory Theatre in Fort Myers presents this intellectual tour de force, which takes place on the brink of World War II, as aging neurologist Dr. Sigmund Freud invites budding author C.S. Lewis to debate the existence of God.


Dec. 27 – Jan. 1


This eight-time Tony Award-winning musical tells the parallel love stories of Orpheus and Eurydice, and Hades and Persephone. Come for the extravagant set, stay for the Grammy Award-winning scores, written by singer-songwriter Anaïs Mitchell.


January 2023


Jan. 14

Scene to be Seen

Naples Art’s annual gala peaks with a wearable art runway show, in which local designers create showstopping designs from unlikely materials, like magazine pages and foraged peacock feathers.


Jan. 14-15, Feb. 11-12, Mar. 4-5

Bonita Springs National Art Festivals

These winter and spring art fairs bring more than 200 juried artists from across the globe to Bonita Springs’ Riverside Park. Proceeds benefit the Centers for the Arts Bonita Springs.


Jan. 14 – Sep. 10

Frida and Her Garden

A year in the making, this garden-within-a-garden recreates Frida Kahlo’s La Casa Azul, her famed blue house in Mexico City, surrounded by blooming botanicals that inspired her works and monumental animal sculptures covered in folk art.


Jan. 19-22

Naples Boat Show

Azimut Yachts, Galeon and Aquila Power Catamarans are just some of the top boat purveyors who fill Naples City Docks for this long-running boater favorite.


Jan. 21-22

25th Annual Art Fest Naples

Hundreds of artists and artisans exhibit at Fleischmann Park in Naples during this show, benefitting STARability Foundation and its programs to help individuals with intellectual and developmental disabilities thrive.


Jan. 21 – Feb 5

Mexicana Fiesta Honoring Frida Kahlo

For Naples Art Districts’ Art & Design Expo, the collective’s artists create vivid murals inspired by the Mexican feminist icon—part of a countywide celebration of Hispanic culture.


February 2023


Feb. 2-5

Cars on Fifth

Naples’ Fifth Avenue South fills with muscle cars, pristine classics and splashy supercars (with an emphasis on Ferraris) for this nearly-20-year-old concourse.


Feb. 3-5

ArtFest Fort Myers

One of Fort Myers’ biggest art festivals fills the historic downtown district with works from more than 200 artists, live music and local food, along with arts and crafts activities to inspire young artists.


Feb. 3 – Mar. 5

The Importance of Being Earnest

In its 25th season, the Florida Repertory Theatre performs the Oscar Wilde classic about two people pretending to be something they are not.


Feb. 7-25

New Works by Reynier Llanes at Harmon Meek

The young, Cuban artist, known for his detailed coffee paintings, was recently named as New Superstar of Southern Art by Oxford America.


Feb. 10 – Mar. 11

Sweeny Todd: The Demon Barber of Fleet Street

Fort Myers’ boundary-pushing Lab Theater brings this cult classic vengeful tale of love and murder to life in Fort Myers.


Feb. 17-19

53rd Everglades City Seafood Festival

There is one rule for everything served at this food festival in the Stone Crab Capital of the World: It must be local. That’s why hundreds flock to the tiny Everglades town in February for fresh Gulf catches and Floridian fare like gator bites and swamp cabbage.


Feb. 18

Edison Festival of Light: Grand Parade

Honoring winter resident Thomas Edison, the 84-year-old parade has marching bands, floats and costumed performers strutting down the streets, starting at Fort Myers High School and ending downtown.


Feb. 19

SWFL VegFest 2023

Hosted at Farmer Mike’s U Pick in Bonita Springs, this ode to plant-forward living features vegetarian food trucks, cooking demos, wellness vendors and talks from doctors and pros spreading the veggie gospel.


Feb. 25-26

Naples National Art Show

For 44 years, Naples Art has curated hundreds of accomplished national artists, working in more than a dozen mediums, for this annual show at Cambier Park in downtown Naples.


March 2023


Mar. 1 – Apr 2

The Sound of Music

The Naples Players perform the five-time Oscar and Tony award-winning, true story of the famed von Trapp Family’s musical adventures.


Mar. 2-4

86th Annual Sanibel Shell Show

Sanibel-Captiva Shell Club hosts this world’s-longest-running shell festival (with all the mollusk-themed art and activities you can handle) at Sanibel Community House.


Mar. 7-11

ECHO Global Food & Farm Festival

Local food insiders, like Rose O’ Dell King of Rosy Tomorrows Heritage Farm and chef David Robbins, descend on the North Fort Myers 57-acre farm for cooking demos, holistic-living workshops (learn to make kombucha) and lunches that draw from ECHO’s eight tropical gardens.


Mar. 11-12

Fort Myers Beach Lions Club Shrimp Festival

Celebrate our Pink Gold with a show-stopping 2-mile parade down Estero Boulevard, a rowdy shrimp-eating contest, the Pink Gold Shrimp Boil at Lynn Hall Beach Park and the crowning of the Shrimp Festival Queen.


Mar. 14-19

Jesus Christ Superstar

This iconic rock opera, written by Broadway legend Andrew Lloyd Webber with music by Tim Rice, celebrates its 50th anniversary with a nationwide tour. See the lively reenactment of Jesus Christ’s final weeks (from Judas’ perspective) on stage at Artis—Naples.


April 2023


Apr. 4-8

Troupe Vertigo Latin Extravaganza

The California group known for blending circus, theater and dance performs alongside Naples Philharmonic—directed by local favorite, Pops conductor Jack Everly—in a tribute to Georges Bizet’s Carmen, a four-part opera based on the novella of the same name.


Apr. 15-22

US Open Pickleball Championships

Naples has easily become the capital for this rising sport, as evidenced by this major tournament that takes place at East Naples Community Park. The pro matches are already sold out, but you can still watch amateurs play on more than 50 courts and get tickets for the Margaritaville Party in the Park on Apr. 23.


Apr. 18-23

Mean Girls

Here’s a nostalgic show for the millennial crowd: Tina Fey’s Broadway production takes the stage at Artis—Naples. Watch the drama unfold as formerly homeschooled Cady enters the cut-throat world of high school cliques.


Apr. 22

Earth Day Festival

Conservancy of Southwest Florida hosts this Earth Day party at its 21-acre nature center in Naples. Kids love the animal encounters, boat tours and riding the new Learning Adventure Bus; grown-ups appreciate the eco lectures, food trucks and nature walks.


Apr. 22

34th Annual “Ding” Darling Day Conservation Carnival

J.N. “Ding” Darling Wildlife Refuge brings its conservation mission to Fort Myers’ Lakes Park, with ranger-guided tours, an urban birding workshop and nature journaling with artist Rachel Pierce.


May 2023



Great Dock Canoe Race

In this Naples tradition that toasts the end of the busy season, year-round locals deck out their canoes in quirky decor and race to the block party and parade on the mainland. Though canceled in the last few years, we have our fingers crossed for a 2023 return.


May 6

27th Annual Taste of the Beach

As season comes to a close, chefs from Fort Myers beach restaurants set up tents at Salty Sam’s Marina to serve their best dishes with hopes of winning the Taste of the Beach Awards. Local favorites including Doc Ford’s Rum Bar & Grille, Pinchers and The Rude Shrimp Co. are known to take home titles in categories ranging from best appetizer to seafood to vegan and vegetarian.


May. 17-21

13th Annual Fort Myers Film Festival

A red carpet leads directors, actors and guests into Sidney & Berne Davis Art Center for opening night of the highly anticipated festival, with locally and internationally produced shorts, indie films and documentaries screened at venues throughout the city.


May 19

“Ding” Darling & Doc Ford’s Tarpon Tournament

Anglers compete to catch the biggest silver king, with tournament proceeds going to fund water and wildlife research at J.N. “Ding” Darling National Wildlife Refuge.  

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