Friends and neighbors,

September’s flying by, and Naples has plenty to keep us busy this week. Tonight is Evening on Fifth, so stroll downtown for live music and take advantage of a dinner deal. The rest of the week is packed: kayaking, cycling, orchids, movies under the stars—you name it. 

A quick heads-up: Nash to Naples tickets are now on sale, and VIP is already halfway gone. Use code NFRN2N26 with our friends at Naples Florida Rentals to save 15%—that means lawn tickets drop under $50. Grab tickets here! (Cool tip: if you’ve ever wanted to learn how to write a song, the festival’s hosting a songwriting workshop with Nashville pros too.) 

Have a great week, and I’ll see you out there.

Cheers,

If you have a tip or event to share, email me at [email protected] — I’d love to feature your favorite finds!

Presented by Naples Florida Rentals: Best Time to Book—Naples Quiet-Season Escape ⛳🌴

Right now is the sweet spot in Naples—September–October means warm Gulf water, open tables, quieter beaches, and the best rates. Claim this golf-front 3BR with a private heated pool + spa as your own resort: sunrise on the fairway, coffee under the lanai, beach by noon, and a twilight swim under the stars.

Why book this home now

  • Family-ready comfort: king primary, queen suite, bunk room, crib + pack-and-play

  • Travel light: children’s dinnerware, books, and a modern kitchen

  • Indoor–outdoor living: covered lanai on the fairway, grill, loungers, pet-friendly fenced yard

  • Close to everything: minutes to beaches, shopping, and dining

Availability: prime late-summer and early-fall weeks are open
Rates: from $179–$249/night (Sept/Oct)
Tip: Quiet-season pricing is live—lock in your dates now before calendars fill.

Top 7 Events This Week: Kayaks, Country Tunes & Cult Classics

  1. The Sound of Music 60th Anniversary Screening (4K Restoration) 

    📅 Fri Sept. 12 - Wednesday, Sept. 17 | Multiple Showtimes

    📍 Alamo Drafthouse, 9118 Strada Pl #8205, Naples

Sixty years later, the hills are still alive—and now in 4K. Catch Julie Andrews in her prime, hum along to “Edelweiss,” and rediscover one of the best films of all time on the big screen. Even if you’ve seen it a dozen times, it’s worth it for the restoration. Get tickets. 

  1. The Jake Hair Band Live @ Whiskey Park

    📅 Friday, Sept. 12 | 8:30 PM – 12:00 AM

    📍 Whiskey Park, 3380 Mercantile Ave, Naples

If you like your country music a little rowdy, this is your night. The Jake Hair Band brings honky-tonk energy with covers of Waylon, Merle, and Gary Stewart. This is the soundtrack to a proper Friday night out. Event Calendar. 

  1. CycleBar Pop-up

    📅 Saturday, Sept. 13 | 9:00 AM or 11:00 AM

    📍 23101 Fashion Drive, Estero

Ever wanted to try an indoor cycling class? Your workout is covered this weekend: CycleBar is popping up with two free indoor cycling classes led by their high-energy instructors. Bring water and get ready for a workout that is equal parts fun and exhausting. Free sign-up.

  1. Clam Pass Kayak Tour

    📅 Saturday, Sept. 13 | 9:00 AM - 12:00 PM

    📍 Clam Pass Beach, Naples

Trade your to-do list for turquoise water and mangrove tunnels this Saturday. Hidden Scenery Kayaking leads this three-hour paddle through Clam Pass, with time to beachcomb and cool off in the Gulf before heading back. $75 pp, reservations required. Call (239) 440-0339 or check their website for excursions.

  1. Bubble Ball 2025 – Wine Tasting for Scholarship Fund

    📅 Saturday, Sept. 13 | 3:00 – 5:00 PM

    📍 Seventh Street Waterfront, 2891 Bayview Drive, Naples

Sip wine, snack on apps, and support local students—it’s a win-win-win. The Naples Junior Women’s Club hosts this fundraiser with tastings, heavy apps, and river views. Tickets fund scholarships for Collier County seniors heading to college (please note tickets are non-refundable and will be donated if you cannot attend). $60/single ticket or $108/double. Tickets.

  1. Movies on the Lawn: Lilo & Stitch (2025)

    📅 Tuesday, Sept. 16 | 7:30 – 9:30 PM

    📍 Event Lawn, Mercato, Naples

Grab a blanket, bring the kids, and settle in for the new live-action Lilo & Stitch under the stars. The movie starts at sundown (around 7:30). Chairs and cozy layers are encouraged (outside drinks are not permitted). Expect a wholesome family movie set in Hawaii with one very chaotic blue alien. Event Info.

  1. Annual Orchid Auction

    📅 Thursday, Sept 18 | 5:30 – 9:00 PM

    📍 Naples Conference Center, 1455 Pine Ridge Road, Naples

Calling all plant lovers: this isn’t your average orchid sale. Expect rare species, prize-winning blooms, and hybrids you can’t find in stores—all donated by growers for auction. Admission is free, and proceeds support Gulf Coast Orchid Alliance programs. Light bites provided. Check their socials for updates!  

Why It Matters

A little planning turns a regular week into great memories. Move your body, support local students, enjoy the arts, and get outside with the people you love.

Until next time,

Elizabeth Bellotti
Editor-In-Chief
Naples, Florida
The Naples Florida Review

P.S. - Check out our sponsor’s vacation homes, comfortable for you, your family, and even your pets. Find out why they currently have more than 500 reviews (all 5 stars!). For more information and to book that perfect vacation, click here.

Love reading The Naples Florida Review? Click here to share with your friends and family.

Put your brand in front of 100,000 passionate Naples Florida Review readers. Let's partner.

"The hard days are what make you stronger." — Aly Raisman

Keep Reading

No posts found