A Walking Tour in Naples, Florida

Until 1885, Naples was known as the Last Frontier. With the exception of Cuban adventurers and fisherman, when Walter N. Haldeman, who published the Louisville Courier-General and General John S. Williams lead some families to the bay that reminded General Williams of beautiful Naples Bay.
There they began a 16-room hotel as well as built a dock that was 1,000 feet long in order to attract the steamboats.
By 1914, the region gained some additional permanent residents. This is the time Edward Crayton started the famous Naples Improvement Company. The new company was created to develop wide avenues lined with palms and waterways.
When the railroad arrived on Jan. 7, 1927, Naples had gained a reputation as a beautiful subtropical paradise.

Historical Places to Visit

Below we have compiled some of the famous houses and structures located on Old Naples. Many of the destinations can be visited on foot, but you could just as easily break up the tour and drive to the ones that interest you the most. Due to the seasonality of Naples, we recommend to call ahead if you plan on visiting any of the museums or businesses listed below. Chances are they will be open but it’s always best to check.
Stop #1: Naples Depot. This is the heart of Naples and the tour’s logical start since the Seaboard Coast line’s arrival assured the growth of the winter resort. It has the style of Spanish Colonial and L. Philips Clarke was its designer. It contains the Bardley Gallery, which is very popular, and a local history museum. You also should go in the railroad cars.
Stop #2: Across US41, to your left, on the Gordon River’s west bank is TIN CITY MARINE MARKET PLACE. Located at 1200 Fifth Avenue, this 40-shop rustic mall has seafood places and tourist shops. Go on an enjoyable boat tour to Naples Bay or Keewaydin Island with one of the companies found on the docks there.
Stop #3: From there, you can drive back and go west on Fifth Avenue, crossing US41 into the shopping district. You’ll find ten amazing blocks of exclusive shops.
If you are visiting during the winter, there’s a trolley that shoppers can use. It’s hard to believe that it was once one of Charles Lindbergh’s landing strips.
Stop #4: Go along Fifth Avenue towards the gulf and you’ll reach Gulf Shore Blvd. When you’re going north, you’re going to reach the newer resorts as well as Lowdermilk Park. This 1,000-foot urban beach has full facilities. If you want to tour the older areas, go south. There’s limited parking access on some of the streets on your right.

Historic Naples Cottages

Below are some of the historic or older homes in Olde Naples.
Stop #5: 670 Gulf Shore Blvd This house was built in 1935 and it’s a Spanish-Mediterranean home with the standard red-tile roof and a huge garage. This was designed by the famous Addison Mizner, who also built Boca Raton. Naples is one of the few places on the west coast that you’re going to find Mizner hoes. The biggest one that you’ll find was built in 1930 called Pineapple Plantation. This house was designed by the incredible George Upton but it’s been altered drastically when it was restored.
Another one of the Mizner gems was found at the bottom of 8th Avenue. This house, called Timken House, was built in 1925 and it’s a two-story Spanish-Mediterranean. Its designer is Phineas Paist, who is also known for University of Miami’s Old Campus and the Venetian Pool. When you reach 9th Avenue, you’re coming close to some of the original development of Naples.
Stop #6: 926 Gulf Shore Blvd This is where the historic Old Hewitt House is found. Built in 1913, this beach house is one story and is heavily shuttered. The Old Indian Canal existed on 10th avenue.
Stop #7: 1144 Gulf Shore Boulevard This is where you find the Mandalay House. Built in 1908, this big beach place can only be reached by an alleyway.
Stop #8: 88 11th Avenue Here you’ll find the Whayne House. Built in 1933, this is one of the neighborhood’s first luxury residences. There are some nice older cottages on 11th avenue is the (7) WHAYNE HOUSE (1933), one of the earliest luxury residences built in neighborhood.
11th Avenue has some nice old cottages, such as the Periwinkle Cottage. Built in 1930, this cottage is found at 123 11th Avenue (Stop #9). Not far from Periwinkle, on 157 11th Avenue (Stop #10) is Westhaven. Built in 1920 by Col Robert West, this massive bungalow is found on four lots.
Going east on 11th and crossing Gulf Shore, you’re going to reach Olde Naples. This is where you’re going to find a few blocks of restaurants and shops. They’re mostly found along Third Street South. There’s a delightful batten and board home named Martha’s Cottage. Built in 1922, it’s found at 205 11th Avenue (Stop #11).
Going south on Third Street, you’re going pass the oldest commercial district in Naples. One of the notable buildings are the Naples Mercantile Building It was built in 1919 and is found at 1117 Third Street (Stop #12). This building is two stories and has a frame structure and is covered in stucco.
On the road’s opposite side is the building known as Olde Naples Building. It was built in 1922 and it’s found at 1148 Third Street (Stop #13). This building was also the Naples Improvement Company’s headquarters, Naples’ first town hall and first movie house. So it has a lot of history!
If you go west on Broad you’ll find a lot of old structures. Some of these are:

  • Stop #14: 239 Broad – 1919 Fisherman’s Lodge, a two-story pine cottage that was moved to the location.
  • Stop #15: 107 Broad – Dr. Earl Baum House built in 1947. Dr. Baum was a naturalist and doctor brought many lovers of nature to the area to study.
  • Stop #16: 88 Broad – 1935 Honeymoon Cottage – a cedar shake building of two stories with a very steep gable.
  • Stop #17: 53 Broad – McKee House built in 1928 is a two-story framed beach house that has a metal stamped roof.

You’ll find the John S. Jones House across the street. It was built in 1922. John was a coal and railroad executive from Ohio who also served as Naples Improvement Company’s head.
Keep going south on Gulf Shore and come to 12th Avenue. Here’s where you’ll find the famous Naples Pier, which is the community’s symbol. Built in 1960, it began back in 1888 as a dock for passengers. It has been built again following 1910, 1926 and 1960 hurricanes and in 1922 following a fire.
The famous General John S. Williams House was built in 1886 and it used to be located at 60 12th Avenue. It was built by Naples’ first developer who then sold it to William Haldeman, who was his friend and who did the majority of additions -four baths and seven bedrooms. Later, the house had been rescued and then relocated to Oak Creek, Bonita Springs. It’s a big victory for Collier County’s history preservation.
Going east on 12th Avenue, you’ll be able to see Palm Cottage. Located at 137 12th Avenue (Stop #18), it was built in 1890 and it’s a two-story tabby home. Walter N. Haldeman lived there and he built the very first hotel at the end of 12th Avenue at Gordon. Henry Watterson, the Louisville editor, did own it. However, today it’s serving as a historic museum and the center for Naples Historical Society.

Bob Vila Tours Naples

In the mid 1990’s, in search of a “cracker” cottage to remodel, Bob goes on a neighborhood tour of Naples, FL, both by car and by boat. You can watch the episode here.

Visiting Naples Soon?

After your walking tour of Naples Florida, return to the beauty and comfort of a home from Naples Florida Vacation Homes. We have a wide selection of homes located all over the Naples area. Whether you’re hoping to squeeze in a few rounds of golf during your visit or you’d like to relax by a private pool, you’ll find the perfect home to fit your needs.
Check out our rentals and book today! We look forward to having you.

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