Fifth Avenue South Strong

Entrepreneurial Endurance When You Need It Most

It’s one thing to have been in business for more than 25 years on Fifth Avenue South, it’s another thing to take a beating from Hurricane Ian and be back in business in no time flat.

Three of our Fifth Avenue South entrepreneurs not only share the same address but have had each other’s backs for decades. During that time, they have become close friends and most recently suffered the wrath of Ian, which flooded their small businesses and resulted in closures and remodeling for all. And yet, Regina’s Ice Cream Pavilion, Petunias of Naples boutique, and Oliver’s Barber Shop are all back open and will celebrate their “come back” and longevity at a grand reopening on Evening on Fifth, January 12. All three businesses are located at 824 Fifth Avenue South.

The stories of these businesses and the fortitude of their owners are in part what makes Fifth Avenue South not only unique, but historic. All three began as locally owned and operated Mom and Pop businesses and over the years have developed a “generational” customer base, serving the needs of their original customers, their children and now their grandchildren.

Regina’s Ice Cream Pavilion

Newly-wed bankers and transplants from New York, Regina and Salvatore Tenaglia drove down Fifth Avenue South in 1988 with one thing in mind—is there a need for a business here that would survive? Fifth Avenue South only had a few stores at the time and was on the downslide.

Regina looked at Sal and said, “What about ice cream, everyone loves ice cream, and it’s so close to the beach?” That was it for the entrepreneurs, who, according to Regina, decided to name the shop after her because “Sal’s sounded like a pizza parlor.”

Regina’s dad came down from Wisconsin to build and run it for the first year, along with the help of Sal’s mom. “It was truly a family affair,” says Regina. Eventually, both Sal and Regina quit banking and worked at the shop full time. “We literally learned as we went along,” says Regina. Although she lost her beloved Sal five years ago, Regina is still engaged in the business, which is one of the most popular destinations on Fifth Avenue South. “I’m not scooping anymore,” she says, “but I’m still hands on.”

Decorated with 50’s memorabilia Sal and Regina collected over the years, Regina’s Ice Cream Pavilion features an antique jukebox along with art and photos of Elvis, the Honeymooners, Betty Boop, and Marilyn Monroe, among others. Regina says, “Most kids today are familiar with only one of the famous personalities: Dorothy from the Wizard of Oz.”

When they first opened, the couple advertised 40 flavors and remarkably have the same number today. Regina says, “My personal favorite is chocolate peanut butter… I eat it all the time.”

However, the most popular flavor and the secret to Regina’s success is the shop’s French vanilla. “If you have a great vanilla, everything else falls in line from cones to sundaes to shakes,” she says with a laugh.

As for being on Fifth Avenue South, Regina is quick to say, “Sal was actually president of the Fifth Avenue Association for a while. We both loved Fifth Avenue South, and today, hurricane and all, I still wouldn’t want to be anywhere else.”

Petunias of Naples

Claudette Willis has loved fashion her whole life. Named “Best Dressed” in high school, Claudette’s first job was as a cashier at Lerners Clothing. She quickly moved up the ranks and became a “road person,” as she calls it, where she helped open stores across the country. Always with the idea of owning her own store in mind, she then moved to Kids Are Us, where she was store manager for a 25,000 sq. ft. operation.

Yet, there remained one skill she needed to perfect and that was as a buyer. She saw an ad for a store manager at a Florida-based boutique. She applied, got the job, and moved to Naples. She spent four years there getting the buying experience she needed for a boutique of her own.

Claudette opened Petunias on Fifth Avenue South in 1997. She speaks lovingly of the name, “I wanted the back wall to be pink and the shop named after a flower and since petunias come in pink, Petunias of Naples was born.”

She had a lot of help early on from her husband Moony Mann, a local musician, and Claudette says, “He was a Godsend during the rebuilding after the flood.”

Since opening its doors, Petunias has truly blossomed. “We’ve gone from mostly beachwear to an eclectic mix of fashion for all ages, all body types and all price ranges,” she notes. “We literally have something for everybody. Plus, we don’t work on commission, so if it’s not right, we help you find something that is.”

Claudette loves being on Fifth Avenue South because so many other business owners are like family. “We all work together; we send customers to each other if we don’t have what they are looking for or if we’re in a different type of business. Regina refers customers to me, and Matt at Oliver’s Barber Shop sends his customers my way to help them with gifts for their wives or girlfriends,” says Claudette, “and Aqua hosts our fashion shows.”

As part of the January 12 grand reopening, Petunias will be featuring a fashion show at Aqua’s. For more information, call 813-579-8890.

Oliver's Barber Shop

One of the oldest Mom and Pop shops on Fifth Avenue South is Oliver’s Barber Shop, which has been in business there for more than 50 years. Oliver Cross and his wife Nancy bought the barber shop in 1972, but it actually was founded in 1951 by original owner Jack Kelly. Oliver’s is still in the family today, as son Matt Cross, who literally grew up with the smell of shaving cream, talc, and hot towels, became the shop’s owner and operator in 2009.

Matt, who followed in his dad’s footsteps, got his barber’s license at Sunstate Academy of Hair Design in Fort Myers. But instead of staying in Naples, Matt headed to New York City, where he worked as a server and also opened his own barber shop. Just as his business was taking off, his dad Oliver had some health issues, and Matt came back to take over the shop on Fifth Avenue South.

Matt recalls fondly how Fifth Avenue South was just a couple of stores when he was growing up. “The only way you could tell it was a city back then was that the phone company was across the street, with a row of phone booths in front of it, and we actually had a bookstore called the “Book Nook.” Haircuts were five bucks,” Matt said with a grin.

“Naples High School football was all the rage, and my dad’s barber shop was always the gathering spot afterwards where the locals would spend hours talking about the games.”

Matt says Naples has changed so much since then, but “it’s still the greatest place to be and just seems like home.”

Matt’s customers are like Regina’s and Claudette’s…multi-generational. His customers range in age from two-years-old to 101. Sometimes in season Matt sees as many as 30 customers in one day.

It looks like barbering may be in the Cross DNA. Matt is a single dad of a darling three-year-old named Ivy. “She’s my little rock star,” says Matt, “and comes to work with me every Saturday.” Who knows, maybe Ivy will one day own Oliver’s and make it a multi-generational small business!

Come to Evening on Fifth on January 12 to meet these three small business owners and see their shops, or better yet drop in anytime for a haircut at Oliver’s, buy a gift at Petunias and top it off with a chocolate peanut butter sundae at Regina’s.

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We are proud and excited to announce the launch of a groundbreaking campaign to benefit the City of Naples and local first responders, to create an iconic piece of art based on the best memories and most joyful moments of everyone in Naples. Join Us!

Mosaic of Memories: The Naples Pier Project

Restoring the community and celebrating the strength and resilience of Naples
Embracing the heart of Naples’ most iconic feature, the Naples Pier, Naples-based Emillions Art has partnered with photo mosaic artist, Robin Austin, to create an iconographic masterpiece. Using thousands of photographs from our community to form the mosaic “tiles,” Robin will create a master work, assembling these tiles into a stunning one-of-a-kind image of the Naples Pier in all its glory.

Once completed, one artwork will be presented for display in City Hall; another will be presented for display at the Naples Fire Rescue Station #1 in downtown Naples. A further 100 limited editions will be available for sale and auction to raise money to benefit both first responders and provide funds to rebuild the pier.

A 40" x 60" limited edition will look perfect in the lobby of your business, your country club, and pride of place in your home, reminding you of the good times, the life, joy, and heart of our community.

Pre-order yours now!


Arts, Culture & Entertainment

Join us here on Fifth Avenue South for these upcoming events.

The Naples Art New Year's Art Fair

January 7 & 8 | 10:00 a.m. - 5:00 p.m.

The Naples Art Institute hosts 200+ artists from all across the country who display their artwork along Fifth Avenue South and in Cambier Park.

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Marilyn's Custom Bag Event

January 13 & 14 | 1:00 p.m. - 5:00 p.m.

Meet with Marilyn and French designer, Aleksandra Gauthier, to design your own luxury leather handbag. Choose your preferred colors and style.

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Naples Artcrafters Fine Art & Crafts Show

January 14 | 10:00 a.m. - 4:00 p.m.

Naples Artcrafters is an association of artists and craft artisans that sponsors juried shows in Cambier Park.

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The Game's Afoot

January 11 to February 5

The Naples Players A murderously funny whodunnit.

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Mud Row

January 5 to 29

Gulfshore Playhouse Mud Row by Tony Award-nominee Dominique Morisseau. Regine must decide the fate of a house she never wanted, the same house where Toshi’s been squatting for three months. Elsie is willing to do anything to move up in the world, while her sister Frances is willing to risk her life to change it. Beneath the roof of one house, generations apart, these women must confront their shared legacies, and each other, in this riveting, humorous, and hopeful story about the love between sisters from one of America’s most vital voices.

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Grand Reopening Fashion Show and Luncheon

January 12 | 12:00 p.m.

Petunias of Naples Help Petunias of Naples celebrate their post-hurricane grand reopening with a fashion show and luncheon! Enjoy lunch by Aqua, a surprise sale, and jewelry by designer Sonia Bailey with Aglaea Jewels. Reservations Required: Call Lisa Jo at 813.579.8890.

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Evenings on Fifth

January 12 | 6:30 p.m. - 9:30 p.m.

An array of live musical performances up and down the sidewalks of Fifth Avenue South, plus dining, shopping, and more.

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Fifth Avenue South Business' Updates

Native Visions Galleries

737 Fifth Avenue South
New bold contemporary wildlife paintings by South African artist Derric van Rensburg.

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In The News

Vote For Your Favorite Restaurant!

The Best of the Gulfshore 2023
We appreciate your time & support in voting for us. Voting ends at midnight on January 31, 2023.

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Celebrate National Spaghetti Day At Pazzo! Cucina Italiana

Abruzzo classic Spaghetti alla Chitarra with homemade veal meatballs, hot sausage, and Sunday gravy available at legendary Italian restaurant on Fifth Avenue South. While there are many varieties of different pasta dishes based on spaghetti, it’s the...

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Transcend Capital Advisors Opens Office In Naples, Florida

Top-ranked wealth management firm expands to South Florida. Transcend Capital Advisors today announced the firm is expanding to Naples, Florida, with an office located at 821 Fifth Avenue South. Transcend is a leading independent registered investment advisor (RIA) that provides a comprehensive...

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Dine on Fifth

Join us here on Fifth Avenue South for a great meal.

See All Restaurants on 5th


Shop on Fifth

Shop a variety of stores here on Fifth Avenue South.

See All Shops on 5th


Play on Fifth

Join us here on Fifth Avenue South for some fun.

See All the Ways to Play on 5th


Concierge Services on Fifth

Many concierge services are offered right here on Fifth Avenue South.

See All Services on 5th


Fifth Avenue South | The Crown Jewel of Naples

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649 Fifth Avenue South I Naples, Florida 34102

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