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 25-27, 2026 is the finale of the Island Hopper Songwriter Fest, which lands on Fort Myers Beach Friday through Sunday, so live music is the headline almost anywhere you go. Saturday brings the usual farmers markets in Fort Myers and North Naples plus a pop-up sale at the Estero Historical Society, Sizzle Dining at Mercato runs through the end of the month, and the Harvest Moon lights the sky Saturday night. Here is what is on the calendar.

Friday, September 25

Fort Myers Beach: the Island Hopper closes out

The big news this weekend is the finale of the Island Hopper Songwriter Fest, which wraps its 2026 run with three days on Fort Myers Beach, September 25-27. Sixty or so mostly free shows by BMI songwriters fill the island from Margaritaville Beach Resort and Pink Shell Beach Resort to other waterfront spots, with sets playing from mid-morning into the evening. It is the easiest place in Southwest Florida to catch live music without a ticket. The full day-by-day lineup is on the official festival site and its schedule page, and if the area is new to you, our Fort Myers area guide introduces the beach and the neighborhoods around it.

Naples: Sizzle Dining at Mercato

If dinner is the plan, Sizzle Dining is still running through September 30 across Collier, Lee, and Charlotte counties, with prix-fixe lunch and dinner menus at more than 130 restaurants. North Naples has a strong cluster at Mercato on Strada Place, including Old Vines, The Hampton Social, Tap 42, and The 239 Naples. The menus and the full list are on the official Sizzle Dining North Naples page. It is an affordable way to sample the places you have been meaning to try, and our Naples area guide covers the neighborhoods around Mercato and North Naples.

Bonita Springs: tribute nights at Stage Bonita

Bonita Springs has a music-friendly weekend at Stage Bonita, the area's dinner-and-show venue, with a Green Day tribute Friday night and a Creed tribute Saturday night. Confirm showtimes and tickets on the venue's Stage Bonita entertainment schedule. For more on the area, our Bonita Springs area guide covers its gated communities and downtown.

Saturday, September 26

Fort Myers and North Naples: the Saturday markets

Market lovers have two steady choices. 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.

Estero: a pop-up sale at the historical society

In Estero, the Estero Historical Society holds its Pop-Up Porch Jewelry Sale Saturday from 10 AM to 2 PM at the society's cottage at 9285 Corkscrew Boulevard, with proceeds supporting the society. It is free and open to the public, a low-key community stop if you are out that way. Details are on the Estero Historical Society events page. If you are considering Estero for a move, our Estero area guide covers its family-friendly communities and the Koreshan State Park area.

Sunday, September 27

Fort Myers Beach: Michael Ray at the Pink Shell Pool Party

The festival's final day is Fort Myers Beach's send-off. Country singer Michael Ray headlines the Pink Shell Pool Party at Pink Shell Beach Resort & Marina on Sunday afternoon, a ticketed poolside show that closes out the 2026 Island Hopper. Times and tickets are published on the festival's official schedule page, and free songwriter sets keep playing around it at beachfront venues through the day.

Marco Island and the Harvest Moon

If you would rather keep the last day 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 choice. And the weekend's quiet star is the Harvest Moon: the full moon nearest the autumnal equinox peaks Saturday, September 26, and it rises near sunset for several evenings running, so Friday through Sunday are all good nights to watch it come up over the Gulf from a beach or bayfront. The Harvest Moon viewing guide from Space.com has the exact times. For more on island living, 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 and our guide to closing costs 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.