Whether you’re a local looking to mix up your routine or a visitor soaking up peak season in Southwest Florida, Naples is packed with things to do this week. From live theater and music to outdoor festivals, art exhibits, and family-friendly activities, the days ahead offer plenty of reasons to get out and explore. Here’s a curated look at what’s happening around Naples and nearby SWFL communities from January 14 through January 21.
🎭 Beau Jest
Date: Jan 14–17
Time: 7:30 PM (Matinee Jan 16 at 2 PM)
Location: The Naples Players, 701 5th Ave S
What it is: A fast-paced romantic comedy following a woman who hires an escort to pose as her Jewish boyfriend — witty, heartfelt, and laugh-out-loud funny.
🎶 Grumpy Old Men: The Musical
Date: Jan 15–16
Time: 7:30 PM (Jan 16 matinee at 2 PM)
Location: TheatreZone, 13276 Livingston Rd
What it is: A musical adaptation of the beloved film, packed with humor, nostalgia, and sharp one-liners about friendship, rivalry, and love.
🏰 Venezia Renaissance Faire
Date: Jan 17–18
Time: 10 AM – 6 PM
Location: Bonita Springs Festival Grounds, 10150 Bonita Beach Rd
What it is: Knights, artisans, live performances, costumes, food, and medieval-style fun for all ages.
🎨 Artis–Naples Performances & Exhibits
Date: Ongoing this week
Time: Various showtimes
Location: Artis–Naples, 5833 Pelican Bay Blvd
What it is: World-class concerts, art exhibitions, and cultural performances throughout peak season.
🧘♀️ Beach Yoga at Vanderbilt Beach
Date: Jan 14–21 (multiple days)
Time: 8 AM
Location: Vanderbilt Beach (near the parking garage)
What it is: Morning yoga by the Gulf — all levels welcome, bring a mat or towel.
🎵 Live Music Night at The Cove
Date: Jan 17
Time: 6 PM – 9 PM
Location: The Cove at Paradise Coast Sports Complex, 3940 City Gate Blvd N
What it is: Outdoor live music, drinks, and relaxed vibes under the lights.
🧹 Naples Pier Beach Cleanup
Date: Jan 17
Time: 9 AM – 11 AM
Location: Naples Pier area
What it is: A community cleanup event helping keep Naples beaches pristine — family-friendly and volunteer-focused.
🎤 Naples Piano Man: Beatles & Stones Tribute
Date: Jan 16
Time: 7 PM
Location: Giuseppe and the Lion, 6160 Livingston Rd
What it is: A lively sing-along piano show featuring classic hits from The Beatles and The Rolling Stones.
🎶 FREE Concert: The Earworms
Date: Saturday, February 7, 2026
Time: 2:00 PM
Location: Lely Presbyterian Church, 110 St. Andrews Blvd., East Naples
What it is: Part of Lely Presbyterian Church’s 2026 Free Concert Series, The Earworms return by popular demand with rich harmonies and a warm blend of country classics and uplifting Christian music. A local favorite, this free afternoon concert is known for its feel-good sound and welcoming community atmosphere — no tickets required.
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