Posted on 9/4/2025 by Juniper Holiday + Home

Embrace Autumn Sunshine in Naples, FL

Warm up this Fall

While much of the country dons cozy sweaters, Naples adds a little sunshine to the season. Fall here is all about perfect temps, shoreline charm, and happening festivals—just the right mix of relaxed beach days, gourmet bites, and cultural flair. Swap falling leaves for Gulf breezes and join us on a tasty, scenic tour of Naples this fall.

A Local Favorite: Stone Crab Festival – Tin City

Stone Crab Festival Logo
Date: October 24th - 26th, 2025

Dig into the famed stone crab claws alongside live music, waterfront views, and artisan vendors. This is a delicious tribute to Florida’s signature seafood—salt, fun, and sunshine included.


Rocktoberfest Half Marathon & 5K – North Collier Regional Park

Rocktoberfest Logo
Date: Sunday, October 5th, 2025
Location: North Collier Regional Park, Naples

Run with a view! Whether you’re chasing a PR or jogging while you groove, this race offers scenic trails, good vibes, and a post-race celebration that truly rocks.


Naples International Film Festival
Reel of Film
Date: October 23rd - 26th, 2025

Filmmakers from around the globe shine at Artis–Naples and Silverspot Cinema. Expect pre-screening galas, Q&As, and stories that linger long after the credits roll.


Brew-Hah-Ha Craft Beer Festival – Mercato
Different Craft Beers
Date: Fall weekend (2025 date TBD)

Local brewers bring over 60 craft beers to Pour it forward—sip, savor, and support Ronald McDonald House Charities of SWFL, all in one hoppy, happy day.


Cars & Coffee 239 – Mercato
Classic Cars in Parking Lot
Date: 3rd Sunday of Every Month

Time: 9:00 a.m. to 11 a.m.

Car enthusiasts and coffee lovers unite! Join the casual crowd at Mercato each fall for exotic rides, local roasts, and a community morning buzz.


Naples Fall Craft & Vendor Market – Cambier Park
Women at Craft Show
Date: November 8th, 2025

Time: 10:00 a.m. to 4:00 p.m.

Local makers, sweet treats, and early holiday finds under swaying palms—this weekend market is the perfect kickoff to cozy season shopping.


Autumn Adventures & Natural Gems

  • Naples Botanical Garden: Garden workshops, nature journaling, and W.O.N.D.E.R. sessions for curious kids and adults alike.
  • Gordon River Greenway: Two miles of walking, biking, and wildlife spotting along the river—ideal for a sunny afternoon stroll.

Stay with Juniper & Love Every Moment

After crab feasts, film screenings, and strolling under palm trees, there’s only one thing left: settling into a home-away-from-home that matches the magic of your Naples getaway.

Juniper Holiday + Home offers thoughtfully designed vacation retreats—coastal-chic flats and family-friendly homes with kitchens, patios, and plenty of space to unwind. Our properties are perfectly placed: a short drive from Tin City, close to Mercato’s buzz, or tucked in quiet neighborhoods for sunset beach strolls.

We’d be thrilled to help you pick the perfect place to rest, rejuvenate, and relive every sunny fall day.

Private Pool in Naples Florida
Ready to plan your Naples escape? Let’s make it easy and brilliant.
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