13 Unique Festivals and Southwest Florida Events To Plan Your Trip
With over 270 sunny days a year, it’s no wonder there are plenty of fun annual events and festivals in southwest Florida with something to celebrate!
If you’re planning a visit to Naples and Marco Island or Fort Myers, Sanibel, Cape Coral and beyond, consider scheduling your vacation dates to coincide with one or more of these fun street festivals and annual events.
A good festival is just about everyone’s favorite thing to do in southwest Florida!
From local arts, crafts, and music to sand sculpting and delicious food, there’s a festival or event for just about every taste and month of the year.
This is especially true in the fall and winter months, when the weather turns perfect again and there’s very little rain.
Locals welcome back the snowbirds and tourists just in time to ring in the holidays.
The local farmers markets gear up for the season and there’s a new energy and anticipation in the air.
The weather is so good during the season in fact, that it’s a pleasure to spend the day strolling a local festival, noshing on whatever suits your fancy, taking in the sights, and letting the kids and grandkids explore.
So mark your calendar and join the celebration.
Here are 13 annual must-visit events and festivals in southwest Florida!
Beautiful glasswork at the Downtown Naples Art Show
Festivals in Southwest Florida
Naples Outdoor Art Festivals
Where: Cambier Park
When: January (Naples New Year’s Art Show), February (Naples National Art Show), and March (Naples Downtown Art Show)
Winter is the perfect time for art and culture lovers to visit Naples, as three distinct National Art Shows come to downtown 5th Avenue.
Artists from around the country are selected to participate in these juried art shows, with the artists themselves onsite to talk about their work and answer questions.
Visitors can stroll the streets and park taking in the amazing work while grabbing bites from local food vendors and listening to live music.
And the range of art you’ll find is inspiring, from modern art and digital media to traditional painting, sculpture, photography, blown glass, and more.
From fine art to folk art and crafts, there’s something for every style.
Cape Coral Art Festival
Where: 1209 Cape Coral Parkway East, Cape Coral
When: January
If you’ve been looking for some fun things to do in Cape Coral, plan on this cool art festival!
Since 1985, the Cape Coral Arts and Music Festival has been showcasing the area’s incredible artistic talent at this impressive festival.
With over 300 artists and craftsmen from around the country, including many local artists, it’s the first and largest juried art fair in all of Lee County.
Visitors will enjoy not just seeing and purchasing amazing artwork but also live entertainment & delicious food.
Fort Myers Art Fest
Where: Downtown Fort Myers Riverfront
When: February
Southwest Florida's premier art festival is a weekend celebration of the arts and one of the best things to do in Fort Myers.
Downtown, the waterfront is filled with talented local and national artists displaying their artwork and chatting with admiring fans.
There’s live music and other entertainment, a high school art competition, and children’s art activities as well.
If you haven’t been to downtown Fort Myers in a while, this is a great event to get reacquainted, take in some of the sites and attractions Fort Myers is known for, and enjoy a day along the River.
Sanibel-Captiva Rotary Club Arts & Crafts Festival
Where: February
When: Sanibel Community House, 2173 Perwinkle Way, Sanibel Island
For over 30 years, this small but impressive local Arts & Crafts Festival has grown from its humble beginnings as a Rotary club breakfast to one of the unique things to do on Sanibel.
While it’s not one of the big regional Southwest Florida festivals, this local festival is worth planning your visit around for a glimpse into Sanibel Island’s inspiring community spirit — a side of the beach resort town visitors rarely get to see and appreciate.
Today, this festival is a juried art show held over President’s Day Weekend. You can stroll the booths surrounding the Community House, with over 100 talented artists from around the country.
There’s plenty of parking and a food court to enjoy a bite to eat.
Swamp Cabbage Festival
Where: Downtown LaBelle
When: February
labelleswampcabbagefestival.org
Head inland from the beautiful beaches of southwest Florida to a unique part of Florida known more for farming than tourism.
For anyone new to LaBelle and the towns around Lake Okeechobee, the annual Swamp Cabbage Festival is a good intro to the area and the unique food at the “heart” of the celebration.
The swamp cabbage being honored here is actually hearts of palm, the soft and delicate heart of the Sabal palm tree, the State Tree of Florida.
For over 23 years, the agricultural community of LaBelle has sponsored this fun event, which typically draws around 35,000 people to the town.
As part of the festival, the Hendry County Cattlemen’s Association also runs their annual Swamp Cabbage Ranch Rodeo, where young cowboys and girls showcase their skills for a chance to qualify for the Florida State finals in Kissimmee.
And what would a country festival be without a beauty pageant, a parade, and an armadillo race!
There’s so much good local fun and a glimpse into some of Florida’s unique and lesser-seen traditions!
Picking Florida stone crabs at the Everglades Seafood Festival
Everglades City Seafood Festival
Where: Copeland Avenue, Everglades City
When: February
If your idea of a good festival in southwest Florida includes some of the freshest local seafood you can find, this might be your nirvana.
Along with great live music, amusement rides, and dozens of craft booths, the real star here is of course the delicious (mostly) local seafood from the nearby waters around the Everglades and south Florida.
Since 1970, this local festival has been a huge draw for visitors and locals alike, and while admission to the festival is FREE, proceeds from beer and wine ticket sales benefit the local community.
Sizzle Restaurant Week
Where: Restaurants in Naples, Cape Coral, Fort Myers, Bonita Springs, Estero, Marco Island
When: Spring and Winter
While not actually a food festival, Sizzle Restaurant Week is one of the most highly anticipated restaurant events in southwest Florida.
The semi-annual, community-driven event not only benefits local residents, visitors, and restaurants, but local college students as well!
During Restaurant Week, over 65 of the best local restaurants from Naples and Marco Island to Cape Coral offer three-course prix-fixe dinner for either $29, $39, or $49 (depending on location).
Some restaurants even offer impressive upgrades on items like wine flights or an added lobster tail, plus savings on a two-course prix fixe breakfast or lunch menu.
Best of all, up to $1 from each meal purchased is donated to Blessings in a Backpack SWFL, a local charity that feeds food insecure elementary students every weekend during the school year.
The Island Hopper Songwriter Fest in Fort Myers and Sanibel Island
Island Hopper Songwriter Fest
Where: Fort Myers, Fort Myers Beach, Sanibel and Captiva islands
When: September
Island Hopper Songwriter Fest website
Do you love groovin’ to the music of awesome local singers-songwriters? How about a little island vibe to go with that?
This exciting music genre seems right at home in southwest Florida.
For ten days every September, the warm island breezes accompany some of the most beautiful voices from around the world in Fort Myers, Sanibel, and Captiva.
The annual Island Hopper Songwriter Fest is a perfect day trip from Naples and showcases over 80 musical artists at venues around the area putting on over 100 shows and performances, from larger stages to small, more intimate venues.
And, as if you needed another reason to spend a few nights on Sanibel and Captiva, some of the coolest music venues are on the islands!
American Sand Sculpting Championship
Where: Fort Myers Beach
When: November
FMBSandSculpting.com
If you’ve never seen a sand sculpting competition, get ready to be amazed.
This goes well beyond building castles in the sand!
The Annual American Sand Sculpting Championship is the largest event of its kind in the United States.
These talented artists use more than 1,000 tons of sand in the process of creating intricate pieces of art that require days of painstaking effort, patience, and a lot of shoveling.
Attendees can enjoy sculpting demonstrations, live entertainment, a variety of food and beverage offerings, kids activities, and endless photo opportunities.
And of course, there’s a wealth of local restaurants along Fort Myers Beach, and more than a few comfy beach bars to cool off with a refreshing beverage nearby.
Cost for a 1 day pass is $5 per person, children ages two and under are free.
Incredible sand sculptures on Fort Myers Beach
Nearby Southwest Florida Festivals
Gasparilla Pirate Festival
Where: Bayshore Boulevard, Tampa
When: January
Since 1904, this colorful festival has been held to celebrate the capture of the city of Tampa by the Spanish pirate Jose Gaspar and his merry Krewe.
These marauding band of buccaneers — or rather, members of the local business elite dressed up as pirates — arrive on a huge Spanish galleon and sack the city.
They make their way down historic Bayshore Boulevard drinking and firing blank shots in the air before sharing their wealth of glittering beads, gold coins and doubloons with the enthusiastic crowd.
The Gasparilla Parade of the Pirates then goes on for 4.5 miles and includes over a hundred festive and bedazzled floats, and dozens of pirate krewes similar to Mardi Gras.
Add in a number of marching bands and live music, and you have one of the most anticipated and well-attended festivals on the Gulf Coast.
Interestingly, while the legend of Jose Gaspar has been at the heart of this event in Tampa for over a century, many southwest Florida locals believe he never actually made it to Tampa, but rather came ashore at Gasparilla Island near Boca Grande, hiding out on this remote Gulf Coast barrier island.
In reality however, Gaspar may not have been at either place — because, according to the Boca Grande Historical Society, he never existed in the first place — and they present a pretty compelling case.
That’s OK.
We still like to believe the shallow waters of the stunning coast around Boca Grande and Gasparilla Island hold treasures beyond just the natural ones, and the Pirate Festival in Tampa is still in good fun.
The Gasparilla Pirate Festival in Tampa
Shark’s Tooth Festival
Where: Venice
When: April
Visit their Facebook Page for more info
Do you love hunting for buried treasure, or fossils and relics eons old?
Then you’ll love hunting for shark’s teeth in nearby Venice and Englewood, and should add the annual Shark’s Tooth Festival to your calendar!
It’s one of the quirkier things to do in SWFL but so much fun, and highly addictive!
Considered to be the unofficial Shark’s Tooth Capital of the World, Venice, Florida is home to more buried teeth from prehistoric sharks like the Megalodon, and one stroll along the beach will show you why.
You’ll find shark teeth with one swipe of your hand in the shallow surf!
To celebrate the city’s unique distinction, the festival brings together fossil collectors and hunting enthusiasts from across the country to show off and sell their shark’s teeth and other fossils.
You’ll even find local tour companies who can take you on a tour to find your own long-buried treasures.
It’s a fun filled day of learning and maybe even honing your shark tooth hunting skills.
There’s also over a hundred artists who attend along with live music and tons of food vendors.
Best of all, proceeds from the event go to support the Sarasota branch of the Special Olympics Florida.
Whatever floats your boat or cracks your claw — whether you dig fossils or sand sculptures (ok, we’ll stop) — there’s an event and festival in Southwest Florida that’s just what you’re looking for.
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