September may signal the beginning of fall in other parts of the country, but here in Southwest Florida, we're still soaking up sunshine, Gulf breezes and plenty of opportunities to get out and explore!

From waterfront fun in Punta Gorda and Charlotte County to arts, entertainment and dining in Sarasota and festivals in historic downtown Venice, September offers plenty of reasons to enjoy our corner of paradise.

Whether you're a longtime local, new to Southwest Florida or visiting the area, here are a few things to add to your September calendar.

🍂 Celebrate Labor Day Weekend in Venice

Kick off September with a trip to historic Downtown Venice for the 17th Annual Labor Day Weekend Venice Craft Festival, happening September 5–6.

Miami Avenue will be filled with talented artisans showcasing handmade jewelry, photography, ceramics, artwork and other unique finds. Admission is free, making it an easy addition to your Labor Day weekend plans.

After exploring the festival, spend some time wandering through the locally owned shops and restaurants along Venice and Miami avenues — or head over to the beach and see if you can find one of Venice's famous shark teeth.

Explore September events in Venice

🎶 Enjoy Live Music in Downtown Venice

September also brings plenty of music to Centennial Park.

The Friday Night Concert Series returns to the gazebo with The Generation Gap/Oldies Review on September 11 and Rocky Rick on September 25. Concerts are scheduled from 7–9 p.m.

Grab dinner downtown, stroll along Venice Avenue and finish your evening with live music under the palms.

🏖️ End the Month with the Venice Beach Party

Here's one worth putting on the calendar early!

The Venice Beach Party is scheduled for September 26 from 1–6 p.m. at Venice Beach, with live music, food trucks and beverages right by the Gulf.

September sunsets on the Gulf Coast are pretty hard to beat, so this could be a fun way to spend one of the final weekends of the month.

🛍️ Shop Local During the Downtown Venice Sidewalk Sale

If shopping is more your speed, Downtown Venice businesses will hold their September Sidewalk Sale September 18–19 from 10 a.m.–4 p.m.

It's a great excuse to explore downtown, hunt for deals and support locally owned businesses at the same time.

Make a day of it with lunch at a local restaurant and a walk through Centennial Park or along Venice Avenue.

🌴 Explore Punta Gorda & Charlotte Harbor

September is also a great time to rediscover Punta Gorda.

Walk or bike along the Harborwalk, explore the shops and restaurants around Fishermen's Village, or spend an afternoon checking out the colorful murals and historic neighborhoods throughout downtown.

For a quieter adventure, visit one of Charlotte County's parks and preserves, get out on the water for a paddle, book a fishing charter or simply find a waterfront restaurant and enjoy the view.

The Charlotte Harbor Event & Conference Center also has several September events on its calendar, including a Fall Arts & Craft Show September 5–6 and the 14th Annual Southwest Florida Martial Arts Open on September 12.

Charlotte Harbor Event & Conference Center calendar

🎭 Catch a Show or Cultural Event in Sarasota

Looking for something indoors when September temperatures are still feeling a little more like summer?

Sarasota's arts and entertainment scene gives you plenty of choices.

September's calendar includes performances and events at venues throughout the area, including Florida Studio Theatre, Sarasota Opera and other Sarasota cultural destinations.

On September 26, Sarasota Opera is scheduled to host its Food & Wine Festival, bringing together food, wine and the arts for a special evening in downtown Sarasota.

Explore Sarasota's September events

🌿 Discover Southwest Florida's Natural Side

You don't need a festival or ticketed event to have a great September weekend.

Sarasota County Parks has a variety of free outdoor and educational programs scheduled throughout the month. In Venice, Shamrock Park Nature Center is open on Saturdays, where visitors can explore fossil, shell, animal and artifact displays.

You can also spend the day exploring places like Lemon Bay, Myakka River, Charlotte Harbor or one of the area's many nature preserves.

Just remember that September is still hot — plan outdoor adventures for the morning or later afternoon, bring plenty of water and keep an eye on the weather.

🌅 Plan a Southwest Florida Sunset Night

Sometimes the best plans are the simplest ones.

Pick a beach, pack a few chairs and make sunset the event.

Venice Beach, Caspersen Beach, Manasota Key and the beaches around Sarasota all offer beautiful spots to end the day. Or stay closer to Charlotte Harbor and enjoy sunset from Punta Gorda's waterfront.

Add takeout from a favorite local restaurant and you've got a pretty perfect Southwest Florida evening without needing an itinerary.

🍽️ Try Somewhere New for Flavorful September

September is also a great month to support local restaurants.

Challenge yourself to try somewhere you've never been before — maybe a waterfront seafood restaurant in Punta Gorda, a cozy café in Venice, a hidden gem in Englewood or one of Sarasota's many downtown dining spots.

And don't forget dessert. Ice cream after a hot September day practically counts as a Southwest Florida tradition!

❤️ Make the Most of September in Southwest Florida

September gives us a little bit of everything: local festivals, live music, beaches, shopping, arts and culture, outdoor adventures and plenty of beautiful sunsets.

Best of all, you don't have to travel far to find something fun to do.

Whether you're exploring Punta Gorda, Charlotte County, Sarasota, Venice or somewhere in between, take a weekend to play tourist in your own backyard and discover something new about the place we get to call home.

What's on your Southwest Florida September bucket list?

Event dates and details may change. Always check directly with event organizers before making plans.