Friends and neighbors,

More than ever, this weekend is for car lovers and anyone with a flair for the dramatic. Naples Cinematheque hosts a Motorsports Film Weekend, complete with director Q&As, while Fifth Ave South fills with Supercars this Saturday. 

Get your art kick at Bonita Arts Festival’s second weekend, or head to the Naples Botanical Garden for their Ikebana Exhibition, a dramatic Japanese floral arrangement style. 

And don’t miss when Chicago comes to town next week at Artis. This Broadway tour won’t be here for long, and you’ll recognize more songs than you think. 

Warm your engines, and get ready for a weekend of style! 

Warmly, 

1.  2026 Naples Motorsports Film Festival
📅 Thursday, February 5 - Saturday, February 7 |  Multiple Showtimes
📍Naples Cinematique, 833 Vanderbilt Beach Rd, Naples

Kick into high gear with Naples Cinematique this weekend for their one-of-a-kind Naples Motorsports Film Festival. This three-day festival will showcase a curated lineup of the best motorsport-themed films, complete with three different director Q&As on Saturday. Get a rare glimpse into the world of competitive racecar drivers and hear directly from the directors who captured it all. Tickets. 

2.  The Paul Simon Songbook
📅 Thursday, February 5 through Saturday, February 7
7:30 PM Performances, 2:00 PM Saturday Matinee
📍Artis—Naples, 5833 Pelican Bay Boulevard, Naples

The Paul Simon Songbook comes to life with Naples Philharmonic Pops, conducted by Stuart Chafetz. The program spans Simon’s six-decade career, from The Sound of Silence and Bridge Over Troubled Water to the rhythm-forward (and personal favorite) Graceland. This is a seated orchestral concert with symphonic arrangements, three vocalists, and enough nostalgia for both chills and tears. Tickets start at $75. 

3.   Adam Carolla Live @ Off The Hook Comedy Club
📅Saturday, February 6 - Sunday, February 7 |  Multiple Showtimes
📍 Off the Hook Comedy Club, 2500 Vanderbilt Beach, Naples

Looking for a laugh-heavy night out? Adam Carolla brings his sharp wit and unfiltered humor to Off The Hook Comedy Club. Known for his quick takes on culture, relationships, and everyday absurdities, this show is best suited for fans who like a bold, smart, and unapologetic show. Tickets. 

4.   Cars on 5th 
📅 Saturday, February 7 | 10:00 AM - 4:00 PM
📍Fifth Ave South, Naples

Chrome shines as Naples Cars on 5th takes over 5th Avenue South. Stroll the street to admire classic, exotic, and custom cars parked curbside against the picturesque backdrop of downtown. Perfect for car lovers, casual browsers, and anyone who enjoys great people-watching. Event info. 

5.   Ikebana Exhibition @ Naples Botanical Garden
📅 Friday, February 6 - Sunday, February 8
📍Naples Botanical Garden, Naples 

Art meets nature at the annual Ikebana Exhibition at Naples Botanical Garden. This three-day event showcases the Japanese art of floral arrangement, emphasizing balance, harmony, and natural beauty. Wander through the gardens to view striking displays, learn about this centuries-old tradition, and enjoy a peaceful, visually inspiring outing surrounded by lush scenery. Event info. 

6.   Bonita Springs National Art Festival
📅 Saturday & Sunday, February 7-8 | 10:00 AM – 4:00 PM
📍Riverside Park, 10450 Reynolds St, Bonita Springs

This is the second of three weekends for the Bonita Springs National Art Festival, with top-tier artists from across the U.S. and beyond. Stroll Riverside Park, chat directly with artists, and browse everything from painting and sculpture to jewelry and glass. Plus, grab food and drinks along the way. The festival supports the Arts Bonita campuses of the not-for-profit Arts Bonita. Event info. 

7.   Chicago 
📅 Tuesday, February 10 - Sunday, February 15 | 12:00—4:00 PM
📍  Artis—Naples, 5833 Pelican Bay Boulevard, Naples

Chicago, Broadway’s longest-running musical, comes to Artis—Naples for a limited engagement. Set in 1920s Chicago, the story follows Roxie Hart and Velma Kelly as their crimes become media spectacles, blurring the lines between justice, celebrity, and ambition. Featuring iconic songs including All That Jazz and Cell Block Tango, the production pairs precise choreography with a sharp, satirical edge. A fast-moving show that remains as relevant today as when it premiered. Tickets. 

Last week we asked: How far would you be willing to travel for events featured in this newsletter (Bonita Springs, Estero, Fort Myers)?

Here’s where you landed: 

Exactly 50% of respondents would be willing to travel an hour (or more!) for a great event. The other half would rather keep it local. Thankfully, Naples has everything we could want right at our fingertips, but if I see something extra special, I’ll be sure to include it!

Thank you to everyone who responded! 

It’s easy to let a Naples weekend slip by on autopilot, especially when life is busy and the calendar is full. This newsletter is here to make it simple to say yes to something local, whether that’s a film screening, a festival stroll, a garden exhibit, or a big night at Artis.

These events are more than “things to do.” They’re how we keep Naples vibrant, support the venues and creators who make this place special, and stay connected to the community we live in.

If you go to anything on this list, hit reply and tell me what you loved, and don’t forget to vote in this week’s poll.

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