In 1938, the Rouse Brothers wrote their hit tune “Orange Blossom Special”, about the famous Seaboard Air Line train that brought frozen northeasterners to the magically sunny wintertime Florida . The eastern, main route of the OBS began in New York and ended in Miami . The western route ended at the Naples Depot, which has been preserved and can still be seen on its original site at the northeast corner of 10th Street and Fifth Avenue South. In the middle of the Great Depression, that train and the winter visitors that it brought to the Haldemans’ grand Naples Hotel were very important to this little fishing village. Back then, fewer than 150 people lived year-round in Naples. Across Fifth Avenue from the Depot, the Frank brothers (Goodlette- Frank Road) owned and operated Naples’ only auto repair garage, and the town’s only school for grades 1 through 12 had just been built on Third Avenue South (now Gulfview Middle School). Collier County founder Barron Gift Collier was still living at the time, and Everglades City was the county seat and real center of business activity.

Of little note at the time, but of great importance to us, Peter Parley Wynn moved to Naples in 1938 and purchased the small Bayview Inn, located in what is now the Crayton Cove business district at the base of the Naples City Docks. Peter and his wife, Vida, also operated a grocery store and restaurant in half of the Bayview building. They had come to Naples from Lakeland, Florida, where they owned another grocery store, which had been left under the control of their 22 year old son, Don.

With the start of World War II, young Don Wynn entered the military, and the Lakeland store was sold. After the war, Don intended to return to central Florida, but he came to Naples to help his parents for a while and, as sometimes happens, “for a while” became forever as Don met and married Annie Merle Echols. The two raised five children, all still living in Naples.

1948 – What a difference 10 years can make! By this time, Naples had a permanent population of almost 600, and there were some 200 individual telephones in the town.

Thanks to John Pulling there was a Naples Board of Realtors. Henry B. Watkins, Sr. had recently arrived and would soon be adding the “Hotel” part to the already established Naples Beach Club golf course. Annie and Don Wynn now had a one year old son, Larry, and Don figured it was time to move “up town”. So, the Wynn’s built Naples ‘ first modern grocery store on the northeast corner of 7th Street and Fifth Avenue South (where the Wynn Building with Yabba’s restaurant is today). It was a rather bold move at the time. That part of Fifth Avenue had just been zoned for commercial use, and when Wynn’s Sunshine Super Market opened, the only building on the half mile of Fifth Avenue South between the market and the beach was the small, 15 room Gulf Hotel at 4th Street.

Just 5 years later, in 1953, the Wynn’s built a new store, twice as large and just to the east of their first Fifth Avenue super market. The grocery business was moved to the new building, and the original building became the birthplace of the other well known Wynn Family enterprise, Sunshine Hardware.

That original super market and then hardware building (eventually Kepp’s men’s clothing store) stood at the corner of 7th Street and Fifth Avenue South until 1999, when it was raised to make way for the new Wynn Building and the Plaza that leads to the Naples Players’ Theater. The later, 1953 building was home to Wynn’s Family Market on Fifth for nearly 50 years and, happily, has been preserved within the new Wynn Building, which runs from Yabba’s Grill, at the west end, to Best of Everything, at the east. If you look closely at the new, modern front of the building, you can see that Aadvisor Rentals, Kilwin’s Chocolates, and Best of Everything are all actually in the old Wynn’s Family Market structure.

In 1964, Don Wynn brought even more convenient shopping to Naples with the construction of a large building on the entire block between 1st Ave and 2nd Ave, fronting on the west side of US 41. From the picture below, you can see Don’s interesting concept of operating the market and hardware as one store. Today, the stores are separated by an interior wall and have different operating hours, but there’s still a Wynn’s Market and Sunshine Hardware at that single address of 141 9th Street (US 41) North.

As the years went by, the Wynn’s expanded their businesses to include grocery and hardware stores in Naples , Bonita Springs , and Golden Gate . In 1985, Don Wynn sold several of the grocery stores to the Kroger company and shifted more of his time and attention to golf and fishing. His youngest son, Tim, then 26, took over direction of the Fifth Avenue store, and the Wynn’s became landlords to the Kroger market at the US 41 location, next to Sunshine Hardware. Eventually, the Kroger lease ended on the US 41 space, and today Tim runs that store, as well as Wynn’s Catering. Tim’s brother, Jerry, ran the hardware stores in Naples, Golden Gate, Bonita Springs, and Estero.

From the beginning, Tim realized that his success as an independent grocery store operator would depend upon offering his customers greater personal service and unique items unavailable in the large chain stores. With that in mind, he added Wynn’s Market home delivery service, expanded the store’s gourmet foods line (now one of the best in the area), and created our “from scratch” fine bakery department featuring a product line that combines international delicacies, American classics, and Wynn Family favorites from his mom, Annie Wynn’s own recipes. Wine and spirits expert Ted Janowitz was brought on board to develop one of the most distinctive wine departments in southwest Florida . Then, in 1992, as a complement to the market, Tim started Wynn’s Catering, now one of the largest and most prestigious catering firms in Collier County.

In his nearly two decades at the helm of the Wynn food operations, Tim has introduced many changes and advancements, but has preserved the core attitudes and principles that his father and grandfather started with. The most important principle being good customer service, which has always been the primary key to Wynn Family success.