On the second Thursday of each month, Fifth Avenue South transforms into a lively, open-air celebration from 6:30 to 9:30 p.m. Known as Evening on 5th, this beloved Naples tradition features live music, al fresco dining, boutique shopping, and the warm glow of string lights overhead.

Musicians line the sidewalks, offering everything from jazz to acoustic favorites, while local restaurants and cafés spill onto the street, creating the perfect setting for a night out. Whether you’re browsing galleries, enjoying dinner under the stars, or simply soaking in the atmosphere, there’s something for everyone.

Pro tip: Arrive around sunset for the best light and a relaxed start to the evening. Street parking and nearby garages make getting there easy, and the stroll is all part of the charm.