September in Florida may signal the beginning of a slower season, but there is still plenty happening around the state.

If you are looking for a reason to get out and explore, I found two very different Florida experiences worth putting on your calendar. One is all about music, storytelling and the magic of historic St. Augustine. The other is a chance to win a coastal getaway right here in beautiful New Smyrna Beach.

Whether you are planning a weekend road trip or simply looking for a little Florida inspiration, here are two things to know about this September.

🎶 St. Augustine Songwriters Festival

September 24–27, 2026 | Historic Downtown St. Augustine

If you love music, especially the stories behind the songs, the 9th Annual St. Augustine Songwriters Festival is one to have on your radar.

Taking place September 24 through 27 in historic downtown St. Augustine, the festival brings together some of the talented songwriters behind songs you may already know and love. Instead of simply watching a performer on a large stage, the festival gives you the opportunity to hear the stories, inspiration and experiences behind the music.

And the setting makes it even more special.

The festival takes place throughout historic downtown St. Augustine, with performances at intimate venues including Colonial Oak Music Park, Prohibition Kitchen, Tradewinds Lounge, DJ’s Clam Shack and Boat Drinks.

Even better?

Admission is free.

The 2026 lineup includes an impressive group of songwriters and artists, including Jeffrey Steele, The Warren Brothers, Anthony Smith, Wynn Varble, Grace West, Jesse Rice, Brian Davis, Craig Campbell, Gordie Sampson, David Tolliver and many more.

One of the things that makes this festival so interesting is the intimate atmosphere. Imagine sitting in historic St. Augustine, listening to the person who actually wrote a song tell you the story behind it before performing it live.

That’s a very different kind of concert experience.

Make a weekend of it

If you are coming from another part of Florida, this would be a great excuse to turn the festival into a weekend getaway.

Spend the afternoon wandering through historic St. Augustine, grab dinner downtown, listen to some live music and enjoy the atmosphere of America’s oldest city.

The festival itself runs for four days, with performances spread across five venues throughout the historic district.

Event: St. Augustine Songwriters Festival
When: September 24–27, 2026
Where: Historic Downtown St. Augustine
Admission: Free

Visit the St. Augustine Songwriters Festival website

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🌊 Enter to Win a Naturally New Smyrna Beach Getaway

If your idea of the perfect Florida experience involves sunshine, the beach and a little exploring, this one might be for you.

The Naturally, New Smyrna Beach Official Giveaway is currently accepting entries for a chance to win a coastal getaway for two.

The prize package is designed to give the winner a taste of what makes the New Smyrna Beach Area such a special place to visit.

The grand prize includes a three night stay for two at SpringHill Suites by Marriott, a guided Dolphin Discovery Boat Tour with the Marine Discovery Center, a full day of Pedego electric bike rentals for two, and a $50 gift card to Flagler Tavern. The winner will also receive two Naturally NSB swag bags filled with New Smyrna Beach keepsakes.

That’s a pretty good Florida getaway.

What the getaway looks like

Imagine waking up just steps from the beach, spending a day exploring the coast by electric bike and then heading out on the Indian River Lagoon to look for dolphins and experience one of Florida’s incredible coastal ecosystems.

And after all that exploring, there is still time to enjoy a meal and a little beach town atmosphere along Flagler Avenue.

The giveaway is free to enter, and the sweepstakes runs through September 30, 2026 at 11:59 PM Eastern Time. The winner will be randomly selected and announced on October 2, 2026.

If you have been thinking about planning a New Smyrna Beach getaway, this is definitely worth entering.

Enter the Naturally, New Smyrna Beach Giveaway

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Two Very Florida Ways to Enjoy September

What I love about these two experiences is how different they are.

One takes you into the heart of historic St. Augustine for an intimate weekend of music, songwriting and storytelling.

The other celebrates the laid back coastal lifestyle that makes New Smyrna Beach such a favorite Florida destination.

And honestly, you don’t necessarily have to choose.

You could make a weekend out of the Songwriters Festival and enter the New Smyrna Beach giveaway while you’re at it.

Because that’s one of the best things about living in Florida.

There is always another town to explore, another local event to discover, another beach to visit and another reason to get out and enjoy where we live.

So add these two to your September list… and go experience a little more of Florida.

Event dates, schedules, performers and giveaway details are subject to change. Be sure to check the official websites for the latest information before making plans.