Destination Main Streets

Naples, Florida

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Visitors flock to Naples, Florida not just for its pristine beachs but also for the upscale shopping and restaurants the downtown has to offer. This has been true for over a hundred years. Naples, located on the southwestern corner of Florida has been a mecca for tourists for a long time. The founders had even given the town the name Naples because the climate had reminded them so much of Naples in Italy. Growth really took off when the Tamiami Trail was completed, connecting Tampa to Miami through Naples. Before the eastern extension through the Everglades to Miami was completed, folks would have to travel north to Jacksonville and back south again to reach Miami. Downtown Naples, part of the Fifth Avenue South district is located at the exact point where the Tamiami Trail makes a 90 degree turn, going from a north-south direction to an east-west direction.

Today, Naples features multiple commercial districts. The largest is the Fifth Avenue South district, located along Fifth Avenue South (of course) between Third Street to the west and Ninth Street to the east. In fact, at the eastern corner is where you will find Tamiami Trail. The Fifth Avenue South district is known for its upscale restaurants, tony boutiques, and a plethora of Mediterranean Revival architecture. Next is the Third Street South district, located roughly between Eleventh Avenue to the north and Fourteenth Avenue to the south. This part of town is frequently known as Old Naples and contains many historical buildings. Another fun area to visit is the Tin City district, where old fishing structures have been converted into a shopping and dining area on the waterfront.

Naples is located in Collier County, Florida and is about 166 miles south of Tampa and 127 miles east of Miami. Generally the heart of Naples is found at the intersection of Fifth Avenue South and Ninth Street South, where the Tamiami Trail (U.S. 41) makes its turn from Tampa on its way to Miami. To find the Third Street district, set your GPS for the intersection of Third Street South and Broad Avenue South. The Tin City district is on Twelfth Street South just south of the Tamiami Trail (U.S. 41). Other nearby Main Street communities include Fort Myers and Fort Myers Beach a few miles north.

Photo Gallery Tour

We start our tour of downtown Naples at the corner of Fifth Avenue and Ninth Street. It is here where the Tamiami Trail (U.S. 41) turns from a southernly direction to an eastern direction. The road was the first direct connection between Tampa and Miami. Before the road was built, if you had to travel from Naples to Miami, you had to drive north to Jacksonville and then back south again.
We start our tour of downtown Naples at the corner of Fifth Avenue and Ninth Street. It is here where the Tamiami Trail (U.S. 41) turns from a southernly direction to an eastern direction. The road was the first direct connection between Tampa and Miami. Before the road was built, if you had to travel from Naples to Miami, you had to drive north to Jacksonville and then back south again.
Here is another building that sits on the corner of Fifth and Ninth. The area is known as Four Corners, and it was here where Naples first began to grow. It was a centralized stopping point for folks traveling between Tampa and Miami.
Here is another building that sits on the corner of Fifth and Ninth. The area is known as Four Corners, and it was here where Naples first began to grow. It was a centralized stopping point for folks traveling between Tampa and Miami.
We now head west down Fifth Street South. Fifth Street is the Main Street for this part of downtown Naples. The area is roughly bounded by Ninth Street to the east and Third Street to the west. Along this route, we find a wide variety of shops and restaurants, many of which are high end to serve the upscale visitors coming to the area.
We now head west down Fifth Street South. Fifth Street is the Main Street for this part of downtown Naples. The area is roughly bounded by Ninth Street to the east and Third Street to the west. Along this route, we find a wide variety of shops and restaurants, many of which are high end to serve the upscale visitors coming to the area.
More shops, businesses and other attractions along Fifth Avenue. As we'll see, real estate is big business in Naples. In this shot, we can see the Real Estate History Museum. We also have an ice cream shop. Many of the shops are what you'd expect close to the beach. If you continue as far west as you can on Fifth Avenue, you'll eventually hit the beaches on the Gulf of Mexico.
More shops, businesses and other attractions along Fifth Avenue. As we'll see, real estate is big business in Naples. In this shot, we can see the Real Estate History Museum. We also have an ice cream shop. Many of the shops are what you'd expect close to the beach. If you continue as far west as you can on Fifth Avenue, you'll eventually hit the beaches on the Gulf of Mexico.
Across we see some restaurants with outdoor seating, surrounded by beautiful landscaping. The Fifth Avenue South district is just one of several districts that can be found in Naples. Later, we'll also explore the Third Street South district and the Tin City area.
Across we see some restaurants with outdoor seating, surrounded by beautiful landscaping. The Fifth Avenue South district is just one of several districts that can be found in Naples. Later, we'll also explore the Third Street South district and the Tin City area.
Here we see some modern-looking architecture along Fifth Avenue South in Naples, Florida.
Here we see some modern-looking architecture along Fifth Avenue South in Naples, Florida.
We make it to the intersection of Fifth Avenue and Eighth Street. Many of the businesses here are high-end. You'll see lush landscaping and other touches, such as the Fifth Avenue South district logo in the middle of the intersection. Also notice the electronic signs pointing visitors to various nearby parking garages.
We make it to the intersection of Fifth Avenue and Eighth Street. Many of the businesses here are high-end. You'll see lush landscaping and other touches, such as the Fifth Avenue South district logo in the middle of the intersection. Also notice the electronic signs pointing visitors to various nearby parking garages.
Along Fifth Avenue, you'll find a wide variety of retailers, many selling apparel, such as this shop with a rather unique store front.
Along Fifth Avenue, you'll find a wide variety of retailers, many selling apparel, such as this shop with a rather unique store front.
In Naples, you'll find an abundance of Mediterranean Revival architecture. Real Estate developers have knocked down a lot of the one story structures along Fifth Avenue and replaced them with highly-ornamented, three-story buildings with offices on the upper floors.
In Naples, you'll find an abundance of Mediterranean Revival architecture. Real Estate developers have knocked down a lot of the one story structures along Fifth Avenue and replaced them with highly-ornamented, three-story buildings with offices on the upper floors.
As we continue down Fifth Avenue we find more businesses. Notice the lush landscaping that separates the street from the wide sidewalks. Also, note the U.S. 41 sign in the background pointing folks towards the famed Tamiami Trail.
As we continue down Fifth Avenue we find more businesses. Notice the lush landscaping that separates the street from the wide sidewalks. Also, note the U.S. 41 sign in the background pointing folks towards the famed Tamiami Trail.
Here we see another block of high-end real estate. This building contains shops, offices, and residential, all with that coveted Fifth Avenue address.
Here we see another block of high-end real estate. This building contains shops, offices, and residential, all with that coveted Fifth Avenue address.
Here we have Kilwin's specializing in chocolate and ice cream. Next door is Best Of Everything. Selling jewelry, accessories and other gifts, this store boasts the largest retail square footage on Fifth Avenue.
Here we have Kilwin's specializing in chocolate and ice cream. Next door is Best Of Everything. Selling jewelry, accessories and other gifts, this store boasts the largest retail square footage on Fifth Avenue.
Further west along Fifth Avenue, we find art galleries and more real estate offices.
Further west along Fifth Avenue, we find art galleries and more real estate offices.
Here we see a wide variety of restaurants and shops within beautiful Mediterranean Revival architecture. As Fifth Avenue commands higher rents, the buildings on Fifth Avenue also go taller to take advantage of the address. However, there aren't many buildings on Fifth Avenue taller than three stories.
Here we see a wide variety of restaurants and shops within beautiful Mediterranean Revival architecture. As Fifth Avenue commands higher rents, the buildings on Fifth Avenue also go taller to take advantage of the address. However, there aren't many buildings on Fifth Avenue taller than three stories.
Between two large buildings is this promenade with outdoor dining. If you head south down this promenade from Fifth Avenue, you'll reach Cambier Park, a large city park and an attraction in its own right. The park contains playgrounds, a Tennis Center, a bandshell, an arts center, a Vietnam War Memorial, and public restrooms.
Between two large buildings is this promenade with outdoor dining. If you head south down this promenade from Fifth Avenue, you'll reach Cambier Park, a large city park and an attraction in its own right. The park contains playgrounds, a Tennis Center, a bandshell, an arts center, a Vietnam War Memorial, and public restrooms.
Across the street we see this restaurant, with this unusual host. Also, notice the sign pointing towards the restrooms at Cambier Park.
Across the street we see this restaurant, with this unusual host. Also, notice the sign pointing towards the restrooms at Cambier Park.
Next door is The Naples Players at the Sugden Community Theater, which shows musicals, comedies, and dramas. In front is Sugden Plaza where other community and theater events are held throughout the year.
Next door is The Naples Players at the Sugden Community Theater, which shows musicals, comedies, and dramas. In front is Sugden Plaza where other community and theater events are held throughout the year.
We get to the corner of Fifth Avenue and Park Street. The Inn On 5th is an upscale boutique hotel in the heart of downtown Naples. The property is made up of two buildings, one across the street from the other.
We get to the corner of Fifth Avenue and Park Street. The Inn On 5th is an upscale boutique hotel in the heart of downtown Naples. The property is made up of two buildings, one across the street from the other.
Here we come across more glamorous architecture along Fifth Avenue. It was a few days before St. Patrick's Day when we were here, hence the festive antique car, driving by.
Here we come across more glamorous architecture along Fifth Avenue. It was a few days before St. Patrick's Day when we were here, hence the festive antique car, driving by.
Some fun-looking gift shops in a one-story building along Fifth Avenue. These one-story buildings are becoming an endangered species in Naples as they are being torn down and replaced with more opulent three-story structures.
Some fun-looking gift shops in a one-story building along Fifth Avenue. These one-story buildings are becoming an endangered species in Naples as they are being torn down and replaced with more opulent three-story structures.
More shops and tropical landscaping along Fifth Avenue. There are a lot of locally owned stores in Naples but also some chains thrown into the mix as well.
More shops and tropical landscaping along Fifth Avenue. There are a lot of locally owned stores in Naples but also some chains thrown into the mix as well.
At the corner of Fifth Avenue and Sixth Street, we have another real estate company and a diner.
At the corner of Fifth Avenue and Sixth Street, we have another real estate company and a diner.
Here we are at the corner of Fifth Avenue and Lake Drive. Definitely some cool people watching opportunities in Naples, especially this guy dressed up and speeding by on a scooter.
Here we are at the corner of Fifth Avenue and Lake Drive. Definitely some cool people watching opportunities in Naples, especially this guy dressed up and speeding by on a scooter.
Across the street, we have more of that Mediterranean Revival architecture along with some more shops, including some chains and a jewelry store.
Across the street, we have more of that Mediterranean Revival architecture along with some more shops, including some chains and a jewelry store.
I did mention that were a lot real estate companies along Fifth Avenue, right? If you're in the market for a new house, you can do a lot of window shopping along this stretch.
I did mention that were a lot real estate companies along Fifth Avenue, right? If you're in the market for a new house, you can do a lot of window shopping along this stretch.
More businesses along Fifth Avenue, including several cafes with an abundance of outdoor seating, which can be really pleasant since you can catch those breezes from the beach only a few blocks away.
More businesses along Fifth Avenue, including several cafes with an abundance of outdoor seating, which can be really pleasant since you can catch those breezes from the beach only a few blocks away.
Here we have Merrihue Mini Park, a well-landscaped piece of land between two commercial buildings. There's plenty of benches and shade in case you need a break from shopping.
Here we have Merrihue Mini Park, a well-landscaped piece of land between two commercial buildings. There's plenty of benches and shade in case you need a break from shopping.
We we see more businesses, such as a real estate office and a financial advisor. Also, check out the lush landscaping along Fifth Avenue.
We we see more businesses, such as a real estate office and a financial advisor. Also, check out the lush landscaping along Fifth Avenue.
This building is a recent addition to downtown Naples. They were just putting the finishing touches on it when I was here. The architecture is more modern than some of the previous buildings we have seen.
This building is a recent addition to downtown Naples. They were just putting the finishing touches on it when I was here. The architecture is more modern than some of the previous buildings we have seen.
This is The Residences at Fifth and Fifth. This recent addition to the neighborhood gets its name from its location at the corner of Fifth Avenue and Fifth Street. If you look carefully, it seems like they have a rooftop deck area as well.
This is The Residences at Fifth and Fifth. This recent addition to the neighborhood gets its name from its location at the corner of Fifth Avenue and Fifth Street. If you look carefully, it seems like they have a rooftop deck area as well.
We continue down Fifth Avenue to find another restaurant with plenty of outdoor seating.
We continue down Fifth Avenue to find another restaurant with plenty of outdoor seating.
Here we have another restaurant and an art gallery, along with some more excellent landscaping.
Here we have another restaurant and an art gallery, along with some more excellent landscaping.
Across the street are more restaurants with outdoor seating in large patio areas. This is one of those one-story buildings along Fifth Avenue that could be targeted soon for redevelopment.
Across the street are more restaurants with outdoor seating in large patio areas. This is one of those one-story buildings along Fifth Avenue that could be targeted soon for redevelopment.
We get to the corner of Fifth Avenue and Fourth Street. Check out all the details from opulent commercial buildings to exquisite landscaping. Attention to detail is even paid to the light posts and street signs.
We get to the corner of Fifth Avenue and Fourth Street. Check out all the details from opulent commercial buildings to exquisite landscaping. Attention to detail is even paid to the light posts and street signs.
More shops, restaurants, and other businesses. Thick landscaping separates the roadway from the pedestrian traffic.
More shops, restaurants, and other businesses. Thick landscaping separates the roadway from the pedestrian traffic.
An interesting mix of architectural styles along Fifth Avenue.
An interesting mix of architectural styles along Fifth Avenue.
Another opulent building on Fifth Avenue. Many of the buildings in this area feature setbacks on the upper floors, which allow for balconies overlooking downtown. Also, notice the attention to detail all the way down to the columns on those upper floors.
Another opulent building on Fifth Avenue. Many of the buildings in this area feature setbacks on the upper floors, which allow for balconies overlooking downtown. Also, notice the attention to detail all the way down to the columns on those upper floors.
A bicyclist rides past on Fifth Avenue. This building seems to take up the entire block. It almost feels like a European palace.
A bicyclist rides past on Fifth Avenue. This building seems to take up the entire block. It almost feels like a European palace.
You'll find clever sculptures like this throughout the Fifth Avenue area of Naples.
You'll find clever sculptures like this throughout the Fifth Avenue area of Naples.
We get to the corner of Fifth Avenue and Third Street. Notice in the middle of the intersection is the Fifth Avenue logo.
We get to the corner of Fifth Avenue and Third Street. Notice in the middle of the intersection is the Fifth Avenue logo.
Across the street are more shops and restaurants. This is the far western edge of the Fifth Avenue commercial district. From here, the beach is about three blocks west. If we head south down Third Street, we'll hit another Naples commercial district.
Across the street are more shops and restaurants. This is the far western edge of the Fifth Avenue commercial district. From here, the beach is about three blocks west. If we head south down Third Street, we'll hit another Naples commercial district.
Here is an example of some of the massive houses, we see just outside of the Fifth Avenue commercial district.
Here is an example of some of the massive houses, we see just outside of the Fifth Avenue commercial district.
Now we head south on Third Street. On the left is Rodgers Park. On the right is the Third Street logo. We pass Eleventh Avenue and are approaching Broad Avenue. The walk down Third Street is about 6 or 7 blocks from the Fifth Avenue South district to the Third Street South district, so keep that in mind before making the trip by foot, especially on a hot day.
Now we head south on Third Street. On the left is Rodgers Park. On the right is the Third Street logo. We pass Eleventh Avenue and are approaching Broad Avenue. The walk down Third Street is about 6 or 7 blocks from the Fifth Avenue South district to the Third Street South district, so keep that in mind before making the trip by foot, especially on a hot day.
We get to the corner of Third Street and Broad Avenue. Here we see the Olde Naples Building, constructed in 1921 by the Naples Company. The building has served as town hall, City Council chambers and courthouse, pharmacy, playhouse, library, movie theater, post office, real estate office, doctor's office, and church before it was finally restored to its original glory.
We get to the corner of Third Street and Broad Avenue. Here we see the Olde Naples Building, constructed in 1921 by the Naples Company. The building has served as town hall, City Council chambers and courthouse, pharmacy, playhouse, library, movie theater, post office, real estate office, doctor's office, and church before it was finally restored to its original glory.
Built in 1919, the Mercantile Building was once home to the Seminole Market with a Wester Union Office upstairs. Eventually it was home to an antique shop and is today home to Campiello's Restaurant.
Built in 1919, the Mercantile Building was once home to the Seminole Market with a Wester Union Office upstairs. Eventually it was home to an antique shop and is today home to Campiello's Restaurant.
We continue south on Third Street to find this interesting building. Here we have space for outdoor dining, a courtyard area and plenty of beautiful landscaping, including benches and fountains.
We continue south on Third Street to find this interesting building. Here we have space for outdoor dining, a courtyard area and plenty of beautiful landscaping, including benches and fountains.
At the corner of Third Street and Twelfth Avenue, we have the Tommy Bahama store and restaurant. This is the site of the first Tommy Bahama restaurant.
At the corner of Third Street and Twelfth Avenue, we have the Tommy Bahama store and restaurant. This is the site of the first Tommy Bahama restaurant.
Definitely a mix of architecture in the Third Street South area. Here we have a Georgian style building with an interesting cupola on the roof.
Definitely a mix of architecture in the Third Street South area. Here we have a Georgian style building with an interesting cupola on the roof.
If we head east on Twelfth Avenue, we find more boutiques and restaurants.
If we head east on Twelfth Avenue, we find more boutiques and restaurants.
Across the street on Twelfth, we see this interesting complex, including shops and restaurants.
Across the street on Twelfth, we see this interesting complex, including shops and restaurants.
We head back to Third Street and continue south. Here we see a high-end restaurant along with some very lush landscaping.
We head back to Third Street and continue south. Here we see a high-end restaurant along with some very lush landscaping.
Next up, we have small plaza along with a concierge station and a clock. The building is painted in a coral color that gives the area a definite Florida feel.
Next up, we have small plaza along with a concierge station and a clock. The building is painted in a coral color that gives the area a definite Florida feel.
Across the street are more shops and restaurants, including this one with a large outdoor patio area. Check out the fountain on the left with the horse statues.
Across the street are more shops and restaurants, including this one with a large outdoor patio area. Check out the fountain on the left with the horse statues.
At the corner of Third Street and Thirteenth Avenue we have more businesses housed in some beachy looking architecture surrounded by palm trees.
At the corner of Third Street and Thirteenth Avenue we have more businesses housed in some beachy looking architecture surrounded by palm trees.
Also, at the corner of Third Street and Thirteenth Avenue we see more shops.
Also, at the corner of Third Street and Thirteenth Avenue we see more shops.
If we head east on Thirteenth Avenue, we have more businesses and cafes, including outdoor seating in a shaded location.
If we head east on Thirteenth Avenue, we have more businesses and cafes, including outdoor seating in a shaded location.
If we head west on Thirteenth Avenue, we have this more modern building with an outdoor restaurant area in the front of it.
If we head west on Thirteenth Avenue, we have this more modern building with an outdoor restaurant area in the front of it.
If we head back to Third Street and continue south, we see what appears to be the side of the building we were looking at in the previous picture.
If we head back to Third Street and continue south, we see what appears to be the side of the building we were looking at in the previous picture.
Continuing south on Third Street, we find some more shops, including a coffee shop and a surf shop. We are just a few short blocks from the beach so a surf shop would make sense. Also notice this area is sometimes referred to as Old Naples. We have reached the southern end of the commercial district, so let's head over to the beach now.
Continuing south on Third Street, we find some more shops, including a coffee shop and a surf shop. We are just a few short blocks from the beach so a surf shop would make sense. Also notice this area is sometimes referred to as Old Naples. We have reached the southern end of the commercial district, so let's head over to the beach now.
We head west towards the beach by way of Twelfth Avenue where we find a neighborhood of historic residences. This is the Palm Cottage. It was built in 1895 and is the oldest house in Naples, Florida. The Naples Historical Society is headquartered there and the house is available for tours.
We head west towards the beach by way of Twelfth Avenue where we find a neighborhood of historic residences. This is the Palm Cottage. It was built in 1895 and is the oldest house in Naples, Florida. The Naples Historical Society is headquartered there and the house is available for tours.
This is the historic Naples Pier. At the Pier, you can find restrooms, showers, a concession stand with covered eating area, and beach supplies.
This is the historic Naples Pier. At the Pier, you can find restrooms, showers, a concession stand with covered eating area, and beach supplies.
Here is a view of the beach at Naples with the Gulf of Mexico in the distance. Let's head over to one more district in Naples before concluding our tour.
Here is a view of the beach at Naples with the Gulf of Mexico in the distance. Let's head over to one more district in Naples before concluding our tour.
Now we enter the Tin City area of Naples. Tin City is a collection of shops and restaurants located on the Gordon River side of Naples. It looks like they were doing some construction when we were here.
Now we enter the Tin City area of Naples. Tin City is a collection of shops and restaurants located on the Gordon River side of Naples. It looks like they were doing some construction when we were here.
Tin City gets its name from the tin-roof buildings. Years ago, this area was the center of the Naples fishing industry, which spanned clam shelling, oyster processing, and boat construction and maintenance.
Tin City gets its name from the tin-roof buildings. Years ago, this area was the center of the Naples fishing industry, which spanned clam shelling, oyster processing, and boat construction and maintenance.
Here is a view inside one of the buildings where we can see a collection of shops.
Here is a view inside one of the buildings where we can see a collection of shops.
We conclude our tour of Naples with a view of some of the restaurants along the waterfront in the Tin City area. When we were there eating, we saw several sight-seeing boat tours travel past, so that's another way to get a good view of the city.
We conclude our tour of Naples with a view of some of the restaurants along the waterfront in the Tin City area. When we were there eating, we saw several sight-seeing boat tours travel past, so that's another way to get a good view of the city.

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