Explore Downtown Naples on Your Next Vacation

Downtown Naples is the hub of entertainment for this southwestern Florida nook. Between iconic local restaurants and the gorgeous views of the water, downtown Naples offers an immeasurable number of activities for all ages. 

We take a thorough look at what makes downtown Fifth Avenue, as well as its sister neighborhood of Third St South, must-see locales when staying at one of our top Naples beachfront rentals.


Downtown Naples hosts an eclectic assortment of fascinating attractions. We highlight four in particular that we consider an essential part of any good Naples vacation. These are all located nearby to our rental properties, and can even be visited on a Naples Segway tour.

Naples Train Museum

This peculiar little oddity highlights the history of trains in southwest Florida. It also features a train you can ride and rooms filled with stunning and accurately handcrafted miniatures. The Train Museum is also associated with the Depot Museum right next door. It features exhibits and showcases expanding to many areas of transportation, including trolleys and vehicles. It is set inside a former train station. 


We highly recommend making time to visit downtown Naples during October for the grand Spooktacular festival. It booms with spooky music, bold costumes, and many activities for all ages.

Cambier Park

This modest-sized community park features lovely little walking trails and courts for tennis and softball. It makes for a fantastic afternoon stop after shopping for a few hours.

The Grape Escape Wine and Food Festival

This December staple is a celebration of Naples’s culinary history. Enjoy top selections from at least 20 participating restaurants, as well as live music and entertainment all along Fifth Avenue. 

We love what Naples delivers for locals and visitors alike all year round. Stay on Naples’s own Main St called Fifth Avenue or venture towards the beach to see the unique and comparatively quieter attractions of Old Naples- Third St. South. 

woman shopping

Shopping and Dining

If downtown Naples is about anything, it’s about shopping and eating until your bags are full and your heart is content. The area includes shopping possibilities in and around Third Street South, in the Fifth Avenue Shops, at Tin City and Venetian Village, and finally the Waterside Shops and the Coastland Center Mall. There is also a great selection of restaurants in Naples, Florida. We cover just a few of our top favorites in the area.

Tin City

Some of the best local shopping is found in Tin City. The shops are wildly eclectic and almost exclusively local. You can find mood rings, candles, antiques, peculiar home items, homemade snacks and desserts, and a dizzying array of possible Naples-specific souvenirs. This is one shopping mall you don’t want to skip.

The Fifth Avenue Mall

This mall makes for a nice complement to Tin City. It features more traditional shopping locations, including many specialty clothing boutiques, home, and design stores, art galleries, and jewelry shops. Some of these include Chico’s, the Emily James Gallery, Bob Baker Shoes, Jamis Boutique, Mirror Mirror Salon, Lovejoy Antiques, Regatta, the Silver Eagle Gallery, and nearly 100 more.


VERGINA is an upscale Italian restaurant with layers of sophistication and elegance. It is beautiful, vibrant, and coated in light from its windows surrounding nearly the entire dining area. It also boasts some of the best pasta specialties in the city.


Citrus Restaurant is a dazzling New American café with a spacious outdoor seating area and a fine assortment of classic seafood cuisine with contemporary flourishes. We recommend the Florida Fish Cakes and the Prince Edward Island Mussels. 

This only scratches the surface of what you can find downtown. Other highlights include Alberto’s on Fifth, Caffe Milano, and Chops City Grill. 

Places to Stay

You can’t make it very far in Naples if you don’t have a fantastic place to call home. Review our full list of Naples vacation rentals to find your dream stay for your dream vacation away. We include a number of pet-friendly rentals if you plan to bring a furry family member along as well as small romantic rentals for a pair. Contact us for additional details or simply secure your stay today.