Naples Is Winning. Growing. And Wrestling With What's Next.

Naples gave us a little bit of everything this week — and that's exactly how we like it. We dug through thousands of reviews to find the five best Mexican restaurants in Naples, while one of the biggest local business stories of the summer took another turn as the founder's son bought back Kelly Roofing with plans to finish customers' roofs. Meanwhile, Naples is outperforming much of the country at the luxury end of the housing market, Southwest Florida is getting three more seasonal flights, NCH notched a Florida first in robotic surgery, and state agents raided two more Collier County gambling spots.

But one story goes deeper than this week's headlines: Naples has become remarkably good at attracting people who have already made it — while struggling to keep some of the young talent trying to make it. We looked at why that matters, what's driving it, and what Southwest Florida could actually do about it.

From tacos and travel to healthcare, housing, development and the future of Naples itself, here's what you need to know this week.

👉 Here's everything you need to know before the weekend.

🔗 What's Happening in Naples This Week: August 20–26, 2026