Things to Do in Naples and Southwest Florida This Weekend, October 16-18, 2026

 

Mid-October in Naples and Southwest Florida is when the calendar starts to feel like season. Boats are on display in Marco Island, shops spill onto the sidewalks of Third Street South, and Halloween fun is popping up across the region. Here is your guide to what is happening from Friday, October 16 through Sunday, October 18.

 

On the Water: The Marco Boat Show

 

The Marco Boat Show runs Friday through Sunday, 10 a.m. to 5 p.m., at the Marco Island Yacht Club and Marco Island Marina Association. It is the largest in-water recreational boat show in the Naples and Marco Island area, with displays from dealers, marinas and marine businesses. General admission is $20, kids 12 and under are free with a paying adult, and a complimentary shuttle brings you to the show. For anyone considering a waterfront home in Naples or Marco Island, it is a great way to see what boating life here really looks like.

 

Family Fun: Halloween Spooktacular at CMON

 

The Golisano Children's Museum of Naples hosts its annual not-so-scary Halloween Spooktacular on Saturday, October 17, with trick-or-treating, crafts, games and Halloween activities throughout the museum. The morning session has sold out, and afternoon sessions run 1 to 3 p.m. and 4 to 6 p.m. Reservations are required. Families looking for more seasonal fun can visit the new Pumpkin Patch at Mercato, Boo at the Zoo at Naples Zoo, or Farmer Mike's Fall Festival in Bonita Springs.

 

Shopping and Strolling: Bon Marché on Third Street South

 

The Bon Marché Sidewalk Sale brings a French flair to Third Street South through Sunday, with more than 25 participating shops and restaurants open 10 a.m. to 7 p.m. Pair it with the Saturday morning Third Street South Farmers Market and lunch at one of the neighborhood's favorite tables.

 

Art, Music and Culture

 

Marco Island Art in the Park fills Veterans' Park Saturday and Sunday, and The Promenade at Bonita Bay hosts a Fall Arts and Crafts Fair on Sunday. Arts Bonita has a full weekend of music, with ThunderBeard's ZZ Top tribute on Friday, blues guitarist Quinn Sullivan on Saturday and Free Fallin: The Tom Petty Concert Experience on Sunday. Artis Naples presents Beethoven and Fanny Mendelssohn Sunday at 3 p.m., and Arynne Wexler headlines Off the Hook Comedy Cafe Friday and Saturday. Live music fills patios all weekend, from Dogtooth Sports Bar in Naples to the Snook Inn on Marco Island.

 

Looking Ahead

 

The Naples International Film Festival comes to Artis Naples October 22 to 25, and the Stone Crab Festival returns to Historic Tin City October 23 to 25.

 

Why This Weekend Matters If You Are Considering Naples or Southwest Florida

 

A weekend like this one shows the range of life here. A morning at the farmers market, an afternoon on the docks, an evening of live music, and the beach never more than a few minutes away. It is not a vacation itinerary. It is simply how people live here, week after week.

If Naples has been on your mind, whether as a second home, a future move, or a place you are still getting to know, I am always happy to be a resource. Reach out anytime, or sign up for This Week in Paradise, my weekly guide to living, playing and owning in Southwest Florida, delivered to your inbox every Friday.

Diane Harris, Realtor and Luxury Properties Specialist

Serving Naples, Bonita Springs, Estero, Marco Island, Collier County, Lee County and the surrounding Southwest Florida area

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