Fifth Avenue South

Honoring Naples’ Past, Celebrating Its Present, and Shaping Its Future

As Naples celebrates its 100th anniversary with events citywide, the Fifth Avenue South Business Improvement District salutes our fair city and is proud to be a part of its storied and remarkable history.

Fifth Avenue South, our original main street for the last 100 years, has enjoyed the distinction of being the major artery in the heart of downtown.

The Avenue was just a spot in the road when Naples was incorporated in 1923. The main street consisted of a few businesses about three blocks east and west of 9th Street South, including Ed Frank’s Garage, the Chamber of Commerce, the telephone company, the train depot, Jack “Doc” Prince’s Naples Liquors, a gas station, Hixon’s Sundries and Club 41.

Ed Frank’s Garage near 10th Street was the first commercial building on Fifth Avenue South. The Franks lived upstairs, and Mrs. Frank, as we are told, would throw her table scraps to alligators in the swamp below. One of the first settlers in the area, the Frank family, owned Naples’ first car dealership, and Ed invented the first swamp buggy.

Above: The Pier

On January 7, 1927, the Orange Blossom Special first rolled into the Naples Seaboard Air Line Passenger Station, and service continued until 1971. The train depot ultimately became a museum.

In the 1930s, there was a small golf course located at the end of Fifth Avenue South near the beach. In 1932, Charles Lindbergh landed his plane somewhere on those links. The Lindberghs had a retreat on Sanibel Island and would often “drop in” to pick up supplies on Fifth Avenue South. During this time, Club 41 was a favorite of locals and visitors alike. Rumor has it Gary Cooper, Lawrence Tibbetts, Gertrude Lawrence and perhaps Gloria Swanson frequented the Club.

Above: Four Corners

Fifth Avenue South continued to flourish during the 1940s and 1950s. In 1949, the town’s first bank, The Bank of Naples, officially opened for business on Fifth Avenue South, catty-corner from the telephone company. Assistant cashier Mamie Tooke, often called the Mother of Naples, taught residents how to budget and save their money. Many depositors later became large landowners. In 1989, The Bank of Naples became Barnett Bank, and today is Bank of America.

In 1948, Don Wynn took a big financial risk and moved the Sunshine Market from the Naples City Dock area to Fifth Avenue South, where he opened the first modern grocery store where Yabba’s restaurant and the Sugden Plaza exist today. The store was a one-stop operation with a butcher shop, baked goods, and everything you could want in terms of groceries. Previously, Naples’ residents had to drive to Fort Myers to find the same offerings.

The store was so successful, that five years later the Wynns built an even larger one where Kilwin’s ice cream and chocolates and Best of Everything are today. The original grocery store site became Sunshine Hardware. Eleven years later, with business booming, both stores were moved to U.S. 41.

By the late 1940s, downtown Naples and Fifth Avenue South were becoming not just a place for commerce, but a cultural destination as well. In 1949, the development of nearby Cambier Park was underway. Today, the park is a destination for concerts, festivals, and movie nights along with tennis, plays, and picnics. The park borders two world-class cultural destinations—the Naples Art Institute and the Norris Center featuring The Gulfshore Playhouse, which is now constructing a stunning world-class professional theater on Goodlette Frank Road.

In 1960, Hurricane Donna struck the Gulf Coast, damaging a number of buildings and landscaping on Fifth Avenue South. By the mid-1960s, Fifth Avenue South was making a comeback, and a real estate boom was in full swing. Unfortunately, newer more modern shopping centers were popping up on the outskirts of downtown, creating new destinations for shopping, dining, and entertainment.

While Fifth Avenue South continued to flourish well into the early 1990s, it felt the impact of growth outside downtown. Naples-area business owners and civic leaders recognized the importance of a cohesive plan for the Fifth Avenue South district and engaged the assistance of renowned urban planner Andrés Duany. With his guidance, an already fashionable street was transformed into Southwest Florida’s premier shopping, dining, cultural, and performing arts destination.

The cultural renaissance fully took root in 1997 with the opening of the Sugden Community Theatre. Home to The Naples Players, the Sugden Theatre planted a seed that has helped 5th Avenue South develop into an enviable cultural scene with a focus on arts and music.

Over the decades, Fifth Avenue South has flourished and reinvented itself. Today, if these sidewalks could talk, they would invite you to stroll up and down our charming avenue under clear blue skies, stopping to shop, meet a friend, get a bite to eat, and enjoy the best of life in Naples, as locals and visitors alike have been doing for a hundred years!


The biggest Christmas showcase in Naples! Enjoy the official Christmas tree lighting on Fifth Avenue South in Sugden Plaza and amazing holiday experiences, including a living nativity by the First Church of the Nazarene, skating rink, live music, Santa Claus, and Fifth Avenue South dining. Join us for this two-day festival. Make your dining reservations today!

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Did you know by Weisberg Wealth Management

In the month of November, indications are that consumer and wholesale inflation rates have significantly eased from their mid-2022 highs. Economists have indicated as much as a 1% rate cut by the end of 2024. If you have questions, please reach out to Rich Weisberg, CRPS, Financial Advisor, RJFS and President at Weisberg Wealth Management at 239-367-7152 or Located at 400 Fifth Avenue South Suite 302.

Securities offered through Raymond James Financial Services, Inc., member FINRA/SIPC Investment advisory services are offered through Raymond James Financial Services Advisors, Inc. Weisberg Wealth Management is not a registered broker/dealer and is independent of Raymond James Financial Services. Investing in oil involves special risks, including the potential adverse effects of state and federal regulation and may not be suitable for all investors.


Arts, Culture & Entertainment

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

Winter Wonderettes

Thru December 17

Gulfshore Playhouse Rock around the Christmas tree with this festive confection of 1960s holiday hits sung in “marvelous” four-part harmony!

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Victor Vasarely: The Absolute Eye

Thru January 28

Naples Art Institute is thrilled to announce our new exhibition featuring the renowned Hungarian-French artist Victor Vasarely.

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Liquid Dreams

December 1 thru 22

East West Fine Art Venetian Artist Annalu creates stunning sculptures that are ever-changing and eternal like life-giving water itself.

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City of Naples Centennial Concert Night with the Ben Allen Band and Rock Republic

December 1 | 6:00 p.m. - 10:00 p.m.

Cambier Park For details on the Centennial Concert Night and to reserve your tickets click below.

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City of Naples Centennial Community Celebration

December 2 | 12:00 p.m. - 4:00 p.m.

Cambier Park For details on the Centennial Community Celebration and to reserve your tickets click below.

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City of Naples Centennial Fireworks Show

December 2 | 6:00 p.m. - 7:00 p.m.

Naples Beaches Fireworks at sunset.

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Christmas at Palm Cottage

December 1 thru 30

Naples Historical Society Celebrate a wonderful time of the year at the merriest place in Naples, Historic Palm Cottage™, during our annual holiday showcase. Tours Tuesday - Saturday, 12:00 p.m. to 4:00 p.m., $13 per person. Reservations recommended. EVENING VISITS FREE Thursdays, Fridays, and Saturdays 4:00 p.m. - 7:00 p.m.

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Christmas Parade

December 5 | 6:00 p.m. - 8:00 p.m.

City of Naples The spectacular march begins on Broad Street South and finishes on 8th Street South.

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Winter Conservatory

December 18 thru 22

Spend the winter break with The Conservatory at Gulfshore Playhouse. Classes for students ages 5-18.

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It’s a Wonderful Life: A Live Radio Play

December 8 & 9 | 8:00 p.m.

The Naples Players in Cambier Park It’s Christmas Eve in 1946. An energetic buzz fills the studio as a cast of actors prepare for their performance of "It’s a Wonderful Life" with a live, listening audience - you!

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The Englishman Fine Art Open House

December 9 | 1:00 p.m. - 4:00 p.m.

Join us for a holiday open house. Beverages and holiday hors d’oeuvres will be served while you enjoy our latest collection of fine art. We look forward to celebrating with you!

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Fine Art & Crafts Show

December 9 | 10:00 a.m. - 4:00 p.m.

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

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Naples Concert Band Concert

December 10 | 2:00 p.m. - 4:00 p.m.

Cambier Park "Joy to the World" A holiday concert with guest artist Craig Greusel.

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Tuba Christmas

December 15 | 6:30 p.m. - 7:30 p.m.

A remarkable evening of music in Sugden Plaza from sousaphone, euphonium, tuba, and baritone horn players.

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Christmas Concert: An Italian Christmas Night

December 16 | 4:00 p.m. and 7:00 p.m.

Naples Woman's Club Andrea Del Principe performs a tribute to the world's greatest tenors.

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New Year's Eve Fireworks

December 31 | 6:00 p.m. - 8:00 p.m.

City of Naples Celebrate the new year by viewing a fabulous display of fireworks off the City of Naples beaches.

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Fifth Avenue South Business' Updates

Journeys 360 Travel

Book your next trip with Journeys 360 Travel. We believe that travel is the only thing that you can buy that truly makes you richer and as cliché as that sounds we could not agree more. Traveling is more than just visiting places and taking pictures, it brings out new ideas and perspectives and is a true investment in yourself. Journeys 360 Travel is a luxury travel agency located on Fifth Avenue South in Naples that strives to provide the best travel services including cruises, safaris, vacation packages, and hotels. Contact us at 239-829-8299.

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Call of Africa's Native Visions Galleries

Bronze Limited Editions by Acclaimed Artist Joseph Quillan. Visit Native Visions Galleries at 737 Fifth Avenue South to experience works by Joseph Quillan.

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Marilyn’s is the best destination for unique, chic apparel and accessories for women. Join us in store or online to find the perfect holiday gift for your loved ones. Located at 375 Fifth Avenue South.

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Emily James Gallery

Emily has been hard at play every day creating amazing pieces of art. Visit her gallery at 720 Fifth Avenue South to see her current pieces.

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Bistro 821

Celebrate New Year’s Eve at Bistro 821
Enjoy our delicious 3 course dinner on New Year's Eve! We have 3 different seating times available. The final seating includes a champagne toast. DJ will start playing at 10:30 p.m.

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In The News

Melissa Martin Joins The Team At Gulf Coast International Properties®

Gulf Coast International Properties® (GCIP) is pleased to announce Melissa Martin, Realtor, has joined the firm. A Naples native, Melissa has real estate written in the fabric of her DNA. She grew up in a family with close ties to the real estate and construction...

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Gulf Coast International Properties® Adopts Stockings For PACE Center for Girls

For the third year in a row, Gulf Coast International Properties® Agents are sponsoring a PACE Center for Girls Angel Tree. The PACE Angel Tree is an opportunity for the brokerage to support the PACE Center in Immokalee to make the holiday extra special by...

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Gulf Coast International Properties Agents Kevin And Jacqui Aizenshtat Host Fundraiser To Support Naples Homeless Charity

Gulf Coast International Properties® Agents and Paradise Region Gruppe Porsche Members Kevin and Jacqui Aizenshtat recently hosted a fundraiser to benefit Maria’s Birthday Wishes for the Homeless. The Thursday, November 9th cocktail hour at Gulf Coast International Properties 5th Avenue Naples office benefitted a charity...

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Naples Historical Society’s Christmas Gala At Historic Palm Cottage™

Presented by Northern Trust. Greetings! Christmastime compels us to reflect on and count our blessings. The past year, we were pummeled by Hurricane Ian, but thanks to some very generous donors, we are back with a spirited vengeance! If you would like to be a...

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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.

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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.

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Fifth Avenue South | The Crown Jewel of Naples

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© 2023 Fifth Avenue South Business Improvement District. All rights reserved.
649 Fifth Avenue South I Naples, Florida 34102

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