Okay, Southwest Florida.

We have officially reached the part of September where I start looking at the weekend calendar and thinking:

Wait...we actually have OPTIONS? 😂

This weekend has a little bit of everything — a huge songwriter festival taking over Fort Myers Beach, a Saturday morning market downtown, free live music, a pretty cool ticketed performance in Bonita and even an intimate songwriter show at one of Fort Myers Beach's most historic spots.

And because Worth Leaving For is supposed to save you from digging through 47 Facebook posts and event calendars yourself, I did that part for you.

Here’s what made the cut for September 25–27.

This Weekend at a Glance

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🎸 1. Island Hopper Songwriter Fest Takes Over Fort Myers Beach

📍 Multiple venues throughout Fort Myers Beach
📅 Friday, September 25–Sunday, September 27
💰 Most performances are FREE

Last weekend Island Hopper was on Captiva.

Then it moved through Cape Coral and downtown Fort Myers.

Now the final weekend belongs to Fort Myers Beach.

Island Hopper Songwriter Fest wraps up its 2026 run with performances all over the beach at places including Margaritaville, DiamondHead, Pink Shell, Matanzas on the Bay, Yucatan Beach Stand and more.

And this isn't just your standard bar-band situation.

These are singer-songwriters performing their music and telling some of the stories behind the songs.

The majority of the festival's 60+ shows are free, although there are some special ticketed performances mixed into the weekend.

Friday alone starts with a FREE Opening Showcase at Margaritaville at 4 PM, followed by free performances at several beach venues that evening.

Why It’s Worth Leaving For

Because you don't have to turn this into one event.

Pick a couple performances.

Grab dinner.

Walk somewhere else.

Catch another songwriter.

Suddenly you've created your own little Fort Myers Beach music crawl.

Stephanie’s Local Tip

Look at the schedule before you leave home.

There are too many performers and venues to just wing this one.

The festival also has a free app that lets you build your own schedule and see maps and performance alerts.

Use it.

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🎹 2. Mia Vassilev: Keys on Fire

📍 Arts Bonita Performing Arts Center
10150 Bonita Beach Road, Bonita Springs

📅 Friday, September 25 | 7:30–9:30 PM
💰 $38–$48 + $4 ticket fee

Here's our date-night/splurge option this week.

And it's definitely different.

Virtuoso pianist Mia Vassilev is bringing Keys on Fire to Arts Bonita Friday night.

The show mixes classical-level piano with boogie-woogie, Latin rhythms, early rock & roll and symphonic pop, backed by double bass and percussion.

So no — we're not talking about two quiet hours of somebody politely playing piano while everyone tries not to cough.

😂

Why It’s Worth Leaving For

This gives us something completely different from all the outdoor festivals and brewery concerts happening this weekend.

It's indoors.

It's Friday night.

And it feels like an actual date-night plan, not just somewhere to wander around.

Stephanie’s Local Tip

This is the expensive one on my list this week, so I'm breaking my usual FREE/under-$25 rule for it.

I'd pair it with dinner in Bonita and make the show the centerpiece of the night.

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🌴 3. Fort Myers Farmers Market

📍 2200 First Street / Downtown Fort Myers Culinary District
📅 Saturday, September 26 | 9 AM–1 PM
💰 FREE admission

Not every Saturday morning needs to involve an elaborate plan.

Sometimes you need:

Coffee.

Something baked.

A little wandering around downtown.

And the possibility of coming home with a plant you absolutely did not intend to buy.

The Fort Myers Farmers Market is running Saturday from 9 AM–1 PM along First Street to Broadway and Broadway to Main Street.

You'll find local produce, seafood, honey, baked goods, cheese, meats, plants, flowers, prepared foods and handmade goods.

Why It’s Worth Leaving For

This is my “I need to get out of the house but I'm not trying to make a whole production out of it” pick.

Admission is free, and the City also lists free on-street parking, with paid garage parking available nearby.

Stephanie’s Local Tip

Go early.

It is still September in Southwest Florida.

Your 9:30 AM farmers-market personality and your 12:30 PM farmers-market personality may be two entirely different people. 😂

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🎶 4. Island Hopper: Music on the Mound

📍 Mound House
451 Connecticut Street, Fort Myers Beach

📅 Saturday, September 26 | 2–4 PM
💰 $50–$75

If you'd rather experience Island Hopper without bouncing between multiple restaurants and bars, this is the completely different way to do it.

Music on the Mound brings songwriters Frank Myers and Lauren Mascitti to historic Mound House for an intimate Saturday afternoon performance.

And the setting is what makes this one interesting.

You're combining live songwriting with one of the most historically significant places on Fort Myers Beach.

Why It’s Worth Leaving For

Island Hopper is happening all over the beach, but this feels much more like an experience than simply catching a free set somewhere.

It's smaller.

It's intentional.

And it's happening at Mound House.

Stephanie’s Local Tip

This one is ticketed, and current availability is limited.

If this is your pick, don't treat it like one of the free Island Hopper performances where you can just wander in.

Get your ticket first.

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🍺 5. Sundown Concert Series at Fort Myers Brewing

📍 Fort Myers Brewing Company
12811 Commerce Lakes Drive #28, Fort Myers

📅 Saturday, September 26 | 6–9 PM
🎶 Edison Schetter & The Rum Runners
💰 FREE

We've officially reached the point where Fort Myers Brewing's Sundown Concert Series has earned recurring status on Worth Leaving For.

Because the formula is pretty hard to argue with:

Live music.

Food trucks.

Beer.

Florida sunset.

Free admission.

This Saturday, Edison Schetter & The Rum Runners take the stage at 6 PM.

There is an optional $30 VIP wristband with reserved seating and a dedicated beer line, but you don't need one to attend.

Why It’s Worth Leaving For

It's one of the easiest Saturday-night plans on the list.

No complicated itinerary.

No expensive ticket.

Just show up.

Stephanie’s Local Tip

For the third week in a row:

BRING. A. CHAIR.

At this point, if you show up without one, I have done everything I can for you. 😂

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🎵 6. Bayside Concert Series: On The Rocks

📍 Bayside Veterans Park, Fort Myers Beach
📅 Sunday, September 27 | 4–7 PM
🎶 On The Rocks
💰 FREE

And we're finishing the weekend by the water.

On The Rocks performs Sunday afternoon at Bayside Veterans Park, right in the downtown district near Old San Carlos Boulevard and overlooking Matanzas Harbor.

It's free, it's waterfront and it runs from 4–7 PM.

Why It’s Worth Leaving For

Because this is exactly the kind of Sunday afternoon people picture when they think about living in Southwest Florida.

Music.

Water.

No ticket.

And you still get home at a reasonable hour because apparently we're adults now.

Stephanie’s Local Tip

Island Hopper is ALSO wrapping up on Fort Myers Beach Sunday.

So don't make two trips.

Check the Island Hopper schedule, catch a songwriter earlier in the day, grab something to eat and finish with On The Rocks at Bayside Veterans Park.

One trip over the bridge.

Multiple things accomplished.

Efficiency. 😂

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🏆 If I Were Picking Just ONE...

Island Hopper on Fort Myers Beach.

I'm giving it the win again because this is your last chance for 2026.

The festival ends Sunday.

And instead of choosing one performance, I'd make this the activity:

Pick two or three free songwriter shows at different venues.

Find somewhere good to eat between them.

Walk around the beach.

Don't rush.

That's the kind of day that reminds you why people spend thousands of dollars to vacation somewhere we can casually visit on a Saturday.

That's Worth Leaving For.

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Here’s Where You Can Get Event Details

Schedules and availability can change, especially for outdoor events and ticketed performances. Check the official event pages before heading out.

Island Hopper Songwriter Fest
Official Island Hopper schedule

Music on the Mound
Mound House event & ticket information

Fort Myers Farmers Market
City of Fort Myers Farmers Market details

Bayside Veterans Park Concert Series
Town of Fort Myers Beach concert schedule

Sundown Concert Series
Fort Myers Brewing concert information

Mia Vassilev: Keys on Fire
Keys on Fire event & ticket information

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Living Here Is More Than Buying a House

It's knowing there's free live music on Fort Myers Beach Sunday afternoon.

It's knowing the farmers market is downtown Saturday morning.

It's knowing a songwriter festival is taking over the beach — and that you can experience most of it without buying a ticket.

That's why every Thursday I dig through what's actually happening around our part of Southwest Florida and pull out the things I think are genuinely Worth Leaving For.

Because knowing an area isn't just knowing what houses cost.

It's knowing how to live here.

Stephanie Barrett
SWFL's Only Inked Agent®
Broker Associate | LPT Realty LLC
📱 941-815-0201
✉️ inkedagentco@gmail.com
🌴 inkedagentflorida.com

No Fluff. No Filter. Just Sold.