What To Do This Weekend in Naples, Bonita Springs, Estero, Marco Island, and Fort Myers

Looking for things to do this weekend in Naples, Bonita Springs, Estero, Fort Myers, and Marco Island? The weekend of September 18-20, 2026 is a strong one for live music and easy outdoor time across Southwest Florida. Fort Myers hosts the free Music Walk on Friday, the Island Hopper Songwriter Fest opens on Captiva Island, Saturday brings a free morning at Corkscrew Swamp Sanctuary and the Fort Myers Farmers Market, and Sunday wraps up with Cars and Coffee 239 at Mercato in North Naples. Here is what is on the calendar.

Friday, September 18

Fort Myers: Music Walk in the River District

Friday night belongs to the Fort Myers Music Walk in the downtown River District. On the third Friday of the month the closed blocks of First and Hendry Streets fill with musicians playing at more than a dozen bars and restaurants, and it is all free from 6 to 10 PM. It is the classic way to spend a Fort Myers evening. Check the official September Music Walk page for the lineup, and if the city is new to you, our Fort Myers area guide introduces the neighborhoods around downtown.

Captiva Island: the Island Hopper opens

A bit over an hour from Naples, the 12th annual Island Hopper Songwriter Fest opens this Friday and runs September 18-27 across Captiva, Cape Coral, downtown Fort Myers, and Fort Myers Beach. The opening weekend lands on Captiva Island with free, unplugged sets by BMI songwriters at venues including the 'Tween Waters Inn & Marina, the Green Flash, the Keylime Bistro, and RC Otter's. Headliners such as Edwin McCain, LOCASH, Michael Ray, and Alexandra Kay play later in the festival, so this opening weekend is the relaxed, all-free version. The full lineup is on the official festival site and its schedule page.

Naples: a Van Halen tribute at Founders Square

If classic rock is more your speed, Completely Unchained, a Van Halen tribute band, plays South Street at Founders Square in Naples at roughly 8 PM on Friday, a club-size show with tickets on Eventbrite. The band lists the date on its official tour page.

Saturday, September 19

Naples: a free morning at Corkscrew Swamp

Saturday morning belongs to nature. Audubon's Corkscrew Swamp Sanctuary, at 375 Sanctuary Road West near Naples, offers free admission from 8 AM to 1:15 PM as its Community Free Day in honor of Latino Conservation Week. The raised boardwalk loops through one of the oldest remaining virgin bald-cypress forests in North America, a gentle 2.25-mile walk that stays cool in the morning. Entry is limited, so check the sanctuary's site for reservation details: corkscrew.audubon.org.

Morning markets: Fort Myers and North Naples

Market lovers have two steady choices on Saturday. The Fort Myers Farmers Market takes over the Downtown Culinary District on First Street from 9 AM to 1 PM, with roughly 40 to 50 local vendors of produce, flowers, and baked goods, and it is listed on the Buy Local Lee directory. Down in North Naples, the Vanderbilt Farmers Market runs Saturdays from 8 AM to noon year-round, so it is a reliable stop any month. For a look at the neighborhoods around it, our Naples area guide covers North Naples and downtown.

Bonita Springs: blues at the Arts Center

Saturday night in Bonita Springs, the Yates McKendree Band plays the Centers for the Arts of Bonita Springs Performing Arts Center at 10150 Bonita Beach Road SE at 7:30 PM, a night of blues and roots rock. Tickets and details are on artcenterbonita.org. If Bonita Springs is on your list, our Bonita Springs area guide covers its gated communities and downtown.

Sunday, September 20

North Naples: Cars and Coffee 239 at Mercato

Sunday morning belongs to Cars and Coffee 239 at Mercato in North Naples (9118/9132 Strada Place), from 9 to 11 AM. It is the third Sunday of the month meet hosted by the Paradise Region Gruppe, a free, family-friendly way to spend the morning walking the cars, coffee in hand. The date is confirmed on the official carsandcoffee239.com site.

Captiva and Marco Island

The Island Hopper's opening weekend on Captiva wraps up Sunday, and if you'd rather keep it simple, Tigertail Beach on Marco Island and the quiet waterfront at Snook Inn (live music on the water most afternoons) are a classic low-key end to the weekend. September is the calm season on the islands, which is exactly the charm. For more on living there, see the Marco Island area guide.

Sunday is also a good day to explore an area you might be considering for a move. Drive through Naples, Bonita Springs, Estero, Fort Myers, or the communities on Marco Island to get a feel for day-to-day life. If you are relocating to Southwest Florida, our relocation guide walks through what to expect. And if you are narrowing down where to buy, this comparison of Naples versus Marco Island for a second home, our guide to closing costs in Naples, and this look at buying a condo in Naples are practical places to start. Past editions of this weekly guide live in the Weekend Guide archive.

Frequently Asked Questions

A note from the author: I'm Catalina Quintero, a bilingual REALTOR with The Miranda Group at Premiere Plus, serving Naples, Bonita Springs, Estero, Fort Myers, and Marco Island. Every week I put this guide together from dated, published event listings, so things can shift and it always pays to confirm the official pages before you head out. If you're exploring Southwest Florida with a move in mind, email or text me any time.