This Week in Naples: Your Guide to Events, Family Fun, and Nights Out

Here’s your full roundup of what’s happening across town — all curated for easy planning.

The Naples Players continue their run of Little Women: The Musical at Sugden Theatre through December 21. It’s a warm, family-friendly production perfect for kicking off the holiday season with a bit of nostalgia and community theater charm. Shows run throughout the week with evening and weekend performances.

At Artis—Naples, the stage is set for The Nutcracker, bringing classical ballet, seasonal music, and that unmistakable holiday magic. It’s one of the most popular December events in town, drawing families, locals, and visitors looking for a festive cultural night out.

The Christmas Club pop-up bar at The Oasis in Naples is in full swing, offering a colorful, over-the-top holiday atmosphere every evening through early January. It's an easygoing night-out pick for groups, couples, or anyone wanting to enjoy themed cocktails and holiday décor without needing reservations.

Johnsonville Night Lights in the Garden Holiday lights remain on at Naples Botanical Garden — through January 4th you can stroll the gardens under thousands of lights, enjoy live music and holiday ambience, and treat yourself to seasonal snacks. A perfect winter-evening outing.

Naples Design District Holiday Stroll from 5:00 PM–8:00 PM. A family-friendly, free evening of lights, music, shopping and dining in the Naples Design District!

If you’re seeking something low-key this week, downtown Naples, Venetian Village, and Fifth Avenue South are lively. Restaurants and bars are beginning their holiday transitions, making this a good time for relaxed dinners, cocktails, or light shopping before December’s full rush sets in.

Riverside's “Wooftop Wednesday” is a fun option for dog owners — a mid-week rooftop hangout where pups are welcome and the atmosphere stays friendly and casual.