As the original settling point of Naples’ first residents, Olde Naples, specifically the Third Street South area, is the birthplace of the beautiful and glamorous downtown area that is so well known today. 

After a sailing trip through Gordon pass to Naples Bay in the later 1800’s, General John S. Williams and Mr. Walter N. Halderman named the pristine expanse of water Naples Bay after the famous Bay of Naples in Italy. 

The two men founded the Naples Town Improvement Company in 1886, marking the beginning of a fast-paced journey to create one of the most sought-after destinations in the world.

The charm and quaint luxury of Olde Naples has been drawing seasonal visitors since the early 1930’s. By this time, the downtown area consisted of a small handful of businesses, a train depot, a telephone company, gas station, and dry good store. 

The Naples Depot provided train service from 1927-1971, and the restored train and Depot still stands today at a historical point of interest and location for many community events.

Olde Naples Florida Today

The famous Fifth Avenue that is known today began with just a couple businesses, including the Rexall Drug Store on the corner of Fifth Avenue South and 8th Street South. 

The Drug Store was a local hub for businessmen and children alike, and today it is known as the Naples 5th Avenue Pharmacy. It wasn’t even until 1949 that the first bank in Naples opened on Fifth Avenue by Mamie Tooke, who is known as the “Mother of Naples” by many. 

Today, Fifth Avenue is a destination in itself for locals and visitors alike with its high-end art galleries, top rated dining, world-class shopping, and quiet relaxation on one of the many palm-shaded benches.

Homes in the Olde Naples area today reflect almost a century of unique architectural styles, from grand beach front estates and picturesque cottages, to brand new multi-story homes and older condos. 

Situated between Port Royal to the south and the Moorings to the North, Olde Naples represents the prime Naples location. 

With every Avenue ending at the beach, walking and biking are popular pastimes, especially to catch one of Naples’ breathtaking sunsets. 

Whether a first-time visitor, a long-time returning guest or a local of Naples, the charm and quiet elegance of Olde Naples is, and will always be, unforgettable.