By the Dawn McKenna Group
Downtown Naples, Florida, is really two streets working in tandem. 5th Avenue South carries the energy, as a wide, tree-shaded run of storefronts and outdoor tables busy from morning coffee to the last dinner seating. A few blocks south, Third Street South slows the pace, trading the bustle for tucked-away courtyards, galleries, and a shorter walk to the sand.
Together, the two streets hold well over 100 storefronts, galleries, live stages, and a must-attend events calendar that reorders itself monthly. At the Dawn McKenna Group, we spend our days across Old Naples, the neighborhood that these districts sit inside, so here is how we would point you through it.
Key Takeaways
- 5th Avenue South is the busier of the two streets, home to the Inn on Fifth, the renovated Sugden Community Theatre, and most of downtown's sidewalk dining.
- Third Street South is the calmer district, dense with galleries and a short walk from the Gulf.
- Cambier Park is downtown's arts hub, with free bandshell concerts from the Naples Concert Band and the Naples Big Band, along with the Naples Art Institute's juried fairs.
How Is Downtown Naples Laid Out?
Downtown Naples, FL, is built around two parallel shopping streets, 5th Avenue South and Third Street South, a few blocks apart and each running toward the beach. Cambier Park sits just off both as a shared green space for concerts and art fairs.
Where to Start Your Adventure in Downtown Naples
- Start on 5th Avenue South near 9th Street and walk west toward the Gulf, ducking into the side courtyards along the way.
- Explore the galleries on Third Street South to find prints, sculptures, watercolor paintings, oil pieces, and more from centuries ago.
- Line up a Saturday visit with the Third Street South Farmers Market, open weekly from 7:30 to 11:30 a.m.
What Can You Do on 5th Avenue South?
5th Avenue South is where downtown Naples spends its evenings in a walkable stretch of boutiques, jewelers, and restaurants with tables on the sidewalk. The shopping leans to fashion and fine jewelry, with names like Marilyn's for European designer clothing, Port Royal Jewelers, and Best of Everything for accessories and gifts. The Inn on Fifth is its flagship luxury hotel, and the avenue gets dressed up for the holidays and closed to cars several times a season for street events.
The avenue's rise is a real estate story, too. In the mid-1990s, the City of Naples set out to revitalize 5th Avenue South and invited The Naples Players to anchor it with a theater, and the Sugden Community Theatre opened in 1998. The company reinvested decades later, reopening the building after a $22 million renovation in 2024.
At the entrance to downtown, Gulfshore Playhouse opened its Baker Theatre and Education Center at Goodlette-Frank Road and 1st Avenue South the same year, adding a full professional stage.
The avenue's rise is a real estate story, too. In the mid-1990s, the City of Naples set out to revitalize 5th Avenue South and invited The Naples Players to anchor it with a theater, and the Sugden Community Theatre opened in 1998. The company reinvested decades later, reopening the building after a $22 million renovation in 2024.
At the entrance to downtown, Gulfshore Playhouse opened its Baker Theatre and Education Center at Goodlette-Frank Road and 1st Avenue South the same year, adding a full professional stage.
What to Know
- The Inn on Fifth is the avenue's signature boutique hotel, with a Club-Level rooftop lounge and a view of 5th Avenue.
- The Naples Players run a full season of plays and musicals at the recently renovated Sugden Community Theatre.
- Gulfshore Playhouse, the area's professional company, now performs at the Baker Theatre at the downtown entrance.
What Is Third Street South Known For?
Third Street South is the quieter, older heart of downtown Naples, with a cluster of shops and restaurants that has kept its low-slung, garden-courtyard look since post-WWII. Its galleries are impressive, and the Gulf is close enough for lunch and a beach walk in one outing.
The shopping here skews to independent fashion and art, with boutiques like Marissa Collections and Maus & Hoffman and galleries like Quidley & Company. This is also the block where Tommy Bahama opened its very first store and restaurant in 1995 and where dining rooms like Sea Salt and Campiello keep a steady following. The Historic Palm Cottage, the 1895 home that the Naples Historical Society still keeps open, stands a block away.
The shopping here skews to independent fashion and art, with boutiques like Marissa Collections and Maus & Hoffman and galleries like Quidley & Company. This is also the block where Tommy Bahama opened its very first store and restaurant in 1995 and where dining rooms like Sea Salt and Campiello keep a steady following. The Historic Palm Cottage, the 1895 home that the Naples Historical Society still keeps open, stands a block away.
What to See
- The Third Street South Farmer’s Market, running since 1994 and open every Saturday with over 60 vendors.
- The Historic Palm Cottage, an 1895 landmark cared for by the Naples Historical Society.
- Christmas on Third, the December lights and holiday celebration that takes over the block.
Which Annual Events Fill the Downtown Calendar?
Downtown Naples keeps a busy calendar that peaks between November and April, with staples that run all year. Much of the arts programming is held in Cambier Park, where the Naples Art Institute holds its juried shows, including the Naples National Art Fair in February and the Downtown Naples Art Fair in March. The park's bandshell hosts free concerts through the winter, the Naples Big Band among them.
The two streets run fun events of their own. At Evening on Fifth, live musicians play along the 5th Avenue South sidewalks for a free night of music, dining, and browsing the shops. The holidays bring the highly anticipated tree lighting ceremony and nativity scene, visits from Santa Claus, and an ice skating rink at the Christmas Walk and Tree Lighting Ceremony, along with “Christmas on Third” held a few blocks south.
The two streets run fun events of their own. At Evening on Fifth, live musicians play along the 5th Avenue South sidewalks for a free night of music, dining, and browsing the shops. The holidays bring the highly anticipated tree lighting ceremony and nativity scene, visits from Santa Claus, and an ice skating rink at the Christmas Walk and Tree Lighting Ceremony, along with “Christmas on Third” held a few blocks south.
How to Plan Around the Calendar
- Visit Naples in February or March for the Naples Art Institute's juried fairs in Cambier Park, including the Naples National Art Fair and the Downtown Naples Art Fair.
- Catch Evening on Fifth for free live music along 5th Avenue South.
- Look up the Cambier Park bandshell lineup for free winter concerts.
- Time a December trip to see Christmas Walk and Tree Lighting Ceremony and Christmas on Third.
FAQs
What Is Downtown Naples, Florida, Known For?
Downtown Naples is best known for its two adjacent shopping and dining streets, 5th Avenue South and Third Street South, plus the galleries, theaters, and Gulf beaches within a few blocks of both.
Is 5th Avenue South Walkable?
Yes, 5th Avenue South is designed around walking, with generous sidewalks, shops, and restaurants running the length of the street. Side streets link it directly to Cambier Park and over to Third Street South.
What Neighborhoods Are Near Downtown Naples?
The neighborhoods closest to downtown Naples are Old Naples, which holds both districts, along with Aqualane Shores and Royal Harbor on the water nearby. Aqualane Shores lies just south of Old Naples, a short walk from the shops. Royal Harbor sits across Naples Bay to the east, within biking distance of both streets.
Where Can You Shop in Downtown Naples?
Downtown Naples splits its shopping between 5th Avenue South and Third Street South. 5th Avenue South leans toward boutiques and fine jewelry, with names like Marilyn's and Port Royal Jewelers. Third Street South runs denser with independent fashion and galleries, including Marissa Collections, Maus & Hoffman, and Quidley & Company.
What Events Happen on 5th Avenue South?
5th Avenue South hosts several signature events. Evening on Fifth fills the sidewalks with free live music, the Naples St. Patrick's Day Parade runs through downtown each March (one of Florida's largest), and December brings the Christmas Walk and Tree Lighting Ceremony.
What Is There to Do in Downtown Naples Besides Shopping?
Plenty. Downtown Naples has live theater at the Sugden Community Theatre and Gulfshore Playhouse, free bandshell concerts in Cambier Park, juried art fairs, a Saturday farmer’s market that runs all year, and beach access.
Experience Life in Downtown Naples for Yourself
Downtown Naples, FL, pays off for anyone willing to park the car and walk. The two districts trade off between them, with the shops, sidewalk dining, and theaters of 5th Avenue South on one side and the galleries, courtyards, and slower pace of Third Street South on the other. Add the concerts and juried art fairs at Cambier Park, the free music of Evening on Fifth, and the Gulf waiting at the end of both streets, and downtown gives you a full day on foot without ever moving your car.
When you are ready to find a home in Naples within reach of it all, connect with our team at the Dawn McKenna Group. We know these streets and the neighborhoods around them, and we would be glad to show you what life a few steps from 5th Avenue South is like.
When you are ready to find a home in Naples within reach of it all, connect with our team at the Dawn McKenna Group. We know these streets and the neighborhoods around them, and we would be glad to show you what life a few steps from 5th Avenue South is like.
