Two Streets, Two Distinct Experiences
From the lively atmosphere of Fifth Avenue South to the historic charm of Third Street South, discover two of Naples' most recognizable destinations and what makes each worth visiting.
Naples has no shortage of beautiful places to visit, from its beaches and waterfront neighborhoods to shopping centers and restaurants throughout the area. But if you really want to get to know Naples, a visit to historic downtown should be on your list.
Fifth Avenue South and Third Street South have been part of Naples for generations. They're known for their restaurants, shops, and special events, but there's much more to these two areas than shopping and dining. Both have played an important role in the city's history, and each has developed its own character along the way.
Third Street South: Where Naples Began
You might be surprised to learn that Third Street South was Naples' original main street, long before Fifth Avenue became the commercial destination it is today. Naples began developing in the late 1880s, when most visitors arrived by boat. The original Naples Hotel and Naples Pier were built in 1889, attracting visitors to what was then a small coastal settlement. Third Street became the center of activity, with a general store, early businesses, and gathering places for residents.
Photo courtesy of Third Street South
The Naples Pier, one of the city's most recognizable historic landmarks, is currently undergoing reconstruction following extensive damage from Hurricane Ian in 2022. Some of the area's early buildings remain, including the Olde Naples Building, where the town council once held meetings. After World War II, businessman and philanthropist Junkie Fleischmann and his wife, Dorette, helped establish shops, galleries, and other businesses that contributed to Third Street's distinctive character.
Today, Third Street is known for its landscaped courtyards, fountains, colorful flowers, restaurants, and boutiques. Much of its appeal comes from the setting itself, making it a lovely area to explore on foot.
One of Third Street's longstanding attractions is its Saturday morning farmers market, which began in 1994. During the winter season, vendors line Third Street South between Broad Avenue and 13th Avenue, offering fresh produce, flowers, baked goods, specialty foods, and more.
During the off-season, the market moves to the nearby Neapolitan parking lot behind Tommy Bahama. It's held year-round from 7:30 to 11:30 a.m. Saturday mornings bring a lively atmosphere to Third Street. Some visitors arrive early to enjoy coffee or breakfast at one of the nearby cafés before browsing the market. Individual street entertainers add to the experience, making it an enjoyable way to spend a morning in Old Naples.
Fifth Avenue South: Naples' Main Street
As Naples grew and automobile travel became more common during the 1920s, Fifth Avenue South gradually developed into the city's main business district. Over the following decades, shops, restaurants, banks, and other businesses opened along the avenue, helping transform the small coastal community into a growing destination for residents and winter visitors.
Today, Fifth Avenue is lined with restaurants, boutiques, galleries, and specialty shops. Sidewalk dining is especially popular, and the avenue becomes particularly lively in the evening as people arrive for dinner or entertainment. There have been changes along Fifth Avenue in recent years. Some longtime independent businesses have relocated, while larger retail brands have begun occupying prominent storefronts. It's an interesting transition for an area that has long been associated with locally owned shops and restaurants.
Cambier Park, Sugden Plaza, and several arts and entertainment venues are also nearby, offering opportunities to combine a downtown visit with other activities.
The Downtown Naples Atmosphere
Photo courtesy of Fifth Avenue South.
One of the things that makes Fifth Avenue and Third Street interesting is the atmosphere. Both are close to established neighborhoods such as Old Naples and Royal Harbor, making them convenient dining and social destinations for nearby residents. They also attract visitors from throughout the Naples area.
And then there are the cars.
It's not unusual to see a Ferrari, Bentley, or Rolls-Royce cruising along Fifth Avenue or parked outside one of the restaurants. The expensive cars are part of the scenery and offer a glimpse into the affluent lifestyle often associated with Naples.
The restaurants reflect that atmosphere as well. Rather than the usual collection of national casual-dining chains, you'll find independent restaurants, sidewalk cafés, and upscale establishments offering everything from Italian cuisine and seafood to fine dining.
There's also a noticeable difference between daytime and evening. During the day, shorts, sundresses, sandals, and casual Florida clothing are common. By evening, you'll see more stylish resort wear, dresses, and occasional sport coats as people arrive for dinner. It's a little more upscale, but certainly not overly formal. Yet the experience isn't exclusively about luxury.
There's something enjoyable about simply strolling the streets, admiring the architecture, browsing the shops, people-watching, or relaxing over coffee and taking in the activity around you.
There's Usually Something Happening Downtown
Fifth Avenue and Third Street aren't just places to shop and dine. Both host events throughout the year, and some have become longstanding Naples traditions.
Evening on Fifth is a popular year-round event held on the second Thursday of each month, from 6:30 to 9:30 p.m. Live musicians perform along Fifth Avenue as visitors enjoy the restaurants, browse the shops, or simply stroll along the street. It's an especially enjoyable outing during the winter months when the evening temperatures are comfortable. Art festivals are another popular attraction, bringing artists and visitors downtown for outdoor shows featuring paintings, photography, sculpture, and other artwork.
And then there's the holiday season.
One of the most unusual and memorable Naples traditions is Christmas on Third, when simulated snow falls over Third Street South on scheduled evenings. With palm trees, holiday lights, music, and decorated storefronts, it's quite a sight to see snow falling in Southwest Florida. The celebration also includes a Christmas tree lighting and other holiday entertainment.
Fifth Avenue has its own holiday tradition with the annual Christmas Walk and Tree Lighting, featuring entertainment, decorations, and festivities along the avenue.
Both areas host additional events throughout the year, so it's worth checking their event calendars to see what's happening during your stay.
Getting Downtown During Season
Now for something that anyone who has spent time in Naples during the winter season can probably relate to: traffic.
Getting to Fifth Avenue or Third Street around lunch or dinner can be frustrating, particularly during January, February, and March. Traffic on US-41 can back up considerably from both directions, and there aren't many convenient alternatives. Part of the challenge is simply the layout of the area. Historic downtown wasn't designed for the volume of traffic Naples experiences today, and the established street configuration limits the number of ways to reach these destinations.
That doesn't mean you should skip a visit. It just helps to plan accordingly.
Dinner reservations are another consideration during the winter season. Many of the popular restaurants on Fifth Avenue and Third Street fill up quickly, especially for prime evening dining times. Depending on the restaurant, you may need to make reservations several weeks or even months in advance. This is especially important when entertaining out-of-town guests or planning dinner for a larger group.
If you have lunch or dinner reservations, allow extra time to get there. The same applies to special events, particularly those involving street closures. There are public parking garages near Fifth Avenue, along with other parking areas throughout downtown. Once you've parked, you may find it more enjoyable to explore on foot rather than moving your car between destinations.
Another suggestion is to make an outing of your visit. Instead of heading downtown for a single restaurant reservation, consider arriving early enough to browse the shops, enjoy the surroundings, and spend some time exploring. After all, there's plenty to see.
Two Areas, Two Different Experiences
Although Fifth Avenue and Third Street are often mentioned together, they offer different experiences.
Fifth Avenue is generally the livelier of the two, with more commercial activity, restaurants, entertainment, and people strolling along the sidewalks. Third Street has a somewhat quieter, more intimate feel, with its landscaped courtyards, historic buildings, and attractive outdoor dining areas. It can certainly get busy, especially during dining hours and special events, but the overall setting is different. Both are worth visiting, and you may find you prefer one over the other.
Getting to Know Another Side of Naples
With so many restaurants, shopping destinations, and places to explore throughout Naples, it's easy to settle into a routine and return to the same familiar spots each season. But there's something special about spending time in the part of Naples where the community began.
Third Street offers a connection to the city's earliest days, while Fifth Avenue reflects how Naples has grown and changed over the years. Together, they offer a glimpse into the history, traditions, and lifestyle that have helped shape the city. They're also great places to take out-of-town guests. A walk along Fifth Avenue, lunch on Third Street, or an evening enjoying the restaurants and atmosphere gives visitors a chance to experience a different side of Naples beyond its beaches.
Traffic may require a little patience during season, but there's no need to rush once you arrive.
If you haven't spent much time exploring Fifth Avenue and Third Street, consider making a day or evening of it this winter. They're two places that help make Naples the destination it is today.
Header photo courtesy of Fifth Avenue South.
About the Author
Jane Rogers is the author of Snowbird Like a Pro and the founder of JRogers Publishing. Having spent several winters in Naples, Florida, she writes about local destinations, seasonal living, and the practical realities of spending part of the year somewhere warmer.
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