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, Marco Island, and Fort Myers? The second weekend of September brings a mix of live music, a year-round farmers market, wine tastings, and quiet beach time across Southwest Florida. Here is what is actually on the calendar for Friday, September 11 through Sunday, September 13, 2026.

Friday, September 11

Fort Myers

Friday is a meaningful evening in Fort Myers. The Fort Myers Philharmonic opens its inaugural season with the Honoring Our Heroes concert at the Barbara B. Mann Performing Arts Hall at FSW, starting at 7:30 PM. The program marks the 25th anniversary of September 11 and honors fallen heroes and first responders with Samuel Barber's Adagio for Strings and Mozart's Requiem. It is a moving way to start the weekend. You can read more about the concert on WGCU.

For a more casual night, the Sam Galloway Concert Series brings country singer Jacob Hackworth to The Ranch Concert Hall & Saloon at 2158 Colonial Boulevard, with doors at 7 PM and opener Ben Gallaher. It is one of the bigger live shows of the weekend in the Fort Myers area.

Bonita Springs

Down in Bonita Springs, the Flamingo Island Flea Market is open Friday from 8 AM to 4 PM, a long-running open-air market where you can wander vendor booths for a few hours. Check the Bonita Springs events calendar for hours and any seasonal details before you head out.

Saturday, September 12

Naples farmers market in the morning

Saturday morning is made for the Vanderbilt Farmers Market at the Galleria Shoppes at Vanderbilt, 2355 Vanderbilt Beach Road in North Naples, open from 8 AM to 12 PM. Unlike some of the seasonal markets in town, Vanderbilt runs year-round on Saturdays, so it is a reliable stop for fresh produce, baked goods, and local vendors even in September.

Naples afternoon and evening

Saturday afternoon, the free, family-friendly Bubble Ball 2026 event takes over the Seventh South waterfront in Naples at 3 PM, a playful outdoor event that works well for families with kids. Later, Wine Around the Water brings a wine tasting party to The Village Shops on Venetian Bay starting at 5 PM, with tastings and an evening stroll along the bay. For live music, Amaury Gutierrez performs at Taberna Ole starting at 7 PM.

Marco Island

On Marco Island, Saturday is a day for the water. Spend the morning at Tigertail Beach, then settle in for waterfront live music at Snook Inn on Bald Eagle Drive, which has music on the water throughout the weekend. It is a classic, low-key Marco Island afternoon.

Sunday, September 13

Sunday afternoon, tennis fans can catch the US Open Men's Final at The Wager Pop-Up Pub Series, a watch party at 801 Gulf Shore Boulevard North in Naples starting at 1 PM. It is a casual, social way to spend the afternoon if you want a bit of live sport with your weekend.

Sunday is also a good day to explore an area you might be considering for a move. Drive through Naples, Bonita Springs, 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.

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