Historic Downtown Naples: Shopping, Dining, Entertainment and More

Take a stroll along the streets and avenues of Historic Downtown Naples, FL where you’ll find more than 100 unique shops and boutiques, art galleries, theaters and fine restaurants tucked between historic buildings and beautiful courtyard gardens. It’s pedestrian-friendly setting offers a dynamic shopping experience that is anchored by the 5th Avenue South and Third Street South districts.

MustDo.com | Historic Downtown Naples, Florida shops and galleries.

Photo credit Debi Pittman Wilkey

Just steps from the Naples Pier and Historic Palm Cottage (the oldest home in Naples) is the Third Street South shopping district. As you stroll up the street you will find lovely shops and delightful outdoor cafes. The area also has a large number of art galleries; boasting more than anywhere else in Southwest Florida. Third Street South has been a hub of fashion and entertainment since the 1930s and has maintained a unique charm that you cannot find in modern shopping developments. On Saturdays they host a farmers market that is brimming with locally grown produce and flowers along side handmade soaps and other craft items.

MustDo.com | Naples, Florida Thursdays on Third, Third Street South events, shops and restaurants.

Photo credit Nita Ettinger

Thursday evenings are a special treat in the Third Street South district, as the area comes alive with music and entertainment. For information on upcoming events be sure to check with the Third Street South Concierge. As you walk along Third Street South, you absolutely must make time to explore the quaint side streets, between Eleventh and Fourteenth Avenues. You will surely delight in exploring the charming shops, boutiques, and restaurants around each corner. If you choose to enjoy Third Street South by car, street parking is available along Third Street South as well as on the side streets.

MustDo.com | Naples, Florida 5th Avenue South Shopping, Restaurants, Entertainment

Photo credit Nita Ettinger

About a half mile north is the 5th Avenue South district. Complimentary public parking garages are located on 8th Street South between 4th and 5th Avenue and between 5th and 6th Avenue South behind Bert’s Seafood. Street parking is also available all along 5th and on side streets, just be aware that during busy periods of the year those spaces fill up quickly.

Art galleries, theaters, and museums share the old Florida charm with locally owned restaurants and shops all along this distinctively Naples upscale shopping and dining district. There is always something special happening on 5th Avenue South, including art festivals, live music, and holiday events. To keep up to date with all the special events on 5th Avenue, visit the 5th Avenue South website.

MustDo.com | Naples Trolley Tours hop on, hop off sightseeing tours Naples, Florida.

Photo credit Nita Ettinger

For shopholics, or if you want to cover more ground and don’t want the hassle of parking, head over to the  Naples Trolley Depot at Tin City. Purchase a ticket for the Trolley, it makes stops at all Naples major shopping areas including Third Street South and 5th Avenue previously mentioned. Your ticket allows you to hop on, hop off all day long, plus you get the added bonus of a little Naples history along the way. Before you head off on the Trolley, peruse the shops at Historic Tin City. This charming old Florida waterfront shopping and dining marketplace is one of Naples oldest and most popular attractions.

MustDo.com | Beautiful fountain at the Waterside Shops in Naples, Florida

Photo credit Waterside Shops

The Waterside Shops is a more traditional mall with great national stores like Saks Fifth Avenue, Apple, and Nordstroms in a spectacular setting with water fountains and lush landscaping. They also offer complimentary valet service. Stop at Mercato to stroll inviting streetscapes and explore the shops and boutiques. You’ll also find that the Mercato offers great indoor and outdoor dining options. The Village on Venetian Bay rounds out Naples shopping choices. A spectacular waterfront location with high-end retail space specializing in one-of-a-kind specialty stores, the majority of them locally owned. From casual to elegant, the latest fashions can be found here.

When you’ve shopped until your ready to drop, enjoy lunch or dinner at one of the restaurants of the area.

Written by:

Nita Ettinger is Co-publisher for Siesta Publications Inc. and the Editor in Chief for Must Do Visitor Guides. Must Do Visitor Guides provides Southwest Florida visitor information through printed magazines and the website MustDo.com. Must Do magazines are published bi-annually and are available at no cost in Sarasota, Lee, and Collier County Chamber of Commerce, visitor information centers, select Southwest Florida hotels, and wherever free publications can be found.