Food & Drink: Central Florida’s Old Diners and Drive-Ins

The interior of Kappy’s Subs remains mostly unchanged since it’s opening. Photo by Roberto Gonzalez

News about Michelin stars and Bib Gourmand nods is nearly constant, with Orlando becoming somewhat of a food mecca for foodies and those who just love variety and quality. But there are times you just want something down-to-earth, no-nonsense, and straightforward, and that, my friends is what you’ll find at these old Central Florida Diners and Drive-Ins.

Kappy’s Subs
Maitland | Established 1967 

You can’t miss the big Kappy’s sign on Orlando Avenue in Maitland. The no-frills restaurant has been a staple since 1967. “We call ourselves a Maitland tradition,” says owner Rachel Milsom. “There are many families whose kids grew up going to Kappy’s; some met their husbands and wives here or rode their bicycles when in middle school.”

This unpretentious diner has been in the same family since its opening. It operates out of an original Valentine Diner, essentially an L-shaped box with just 12 swiveling bar stools with weathered cushions, overlooking the kitchen where a calm and collected staff sweats through order after order of burgers, strawberry milkshakes, and Philly cheesesteaks. Valentine Diners were prefab trailers designed to be run by just a few people, and while they’re not being made anymore, the utilitarian charm makes you wonder why they couldn’t make a resurgence someday. The youngest generation of the Caplan family has recently added their own flair to the family business, including a trendy food truck and some innovative additions to the menu. Still, the real magic is simply being able to sit in the roadside dining room of this Maitland-based icon and watch the world drive by on 17-92. 

Under a canopy, folks order at the window and grab a seat at a picnic table out front. Inside there’s a diner-style counter with 12 faded red vinyl stools. Kappy’s is known for its cheesesteak sandwiches—brown beef with American cheese and the traditional Philly. Everything here is handmade from scratch, including favorites like chili, and roast pork, from Kappy’s special recipe, for its Cubans. But what surprises customers are the milkshakes. “We don’t use mixes. We make hand-dipped real ice cream milkshakes. That’s something you just don’t find anymore,” says Milsom. | kappyssubsfl.com

Linda’s Winter Park Diner offers booths and counter stools for hungry guests. Photo by Roberto Gonzalez.

Linda’s Winter Park Diner
Winter Park | Established 1950s 

Located in the heart of Winter Park, Linda’s Winter Park Diner has been a stalwart of the local culinary scene since the 1950s. This iconic diner is known for its friendly atmosphere, speedy service, and diverse menu options, making it a cherished breakfast and lunch spot for generations of Floridians and tourists alike.

The heart and soul of the diner, Linda D’Auria, has been its proud owner for nearly 34 years. Under her seasoned stewardship, the Winter Park Diner has maintained its classic charm and distinct identity while continually adapting to the changing tastes and preferences of its patrons.

Linda’s hands-on management style, coupled with her unwavering commitment to delivering quality food and service, has been instrumental in securing the diner’s reputation as a reliable and affordable place to dine. Her love for her customers and dedication to the diner’s legacy are palpable in the cheerful ambiance that greets each visitor.

Fast, friendly service is a hallmark of the Winter Park Diner. Linda and her team work tirelessly to ensure that every customer feels at home and every meal is served promptly – a testament to the diner’s steadfast commitment to exceptional customer experience. Sadly, Linda’s is closing at the end of this month, so hurry up and check it out before it’s gone! | winterparkdiner.com

For the road trippers, these spots are worth the drive, and won’t sting your wallet either! 

MoonLight Drive-In provides car-side service and amazing food. Photo by Catherine Walters.

MoonLight Drive-In
Titusville | Established 1964 

Established in 1964, MoonLight is an original, carhop themed restaurant named to honor the Apollo program and their many missions to the moon. Almost 60 years later, you can still get the classic burger, hot dog, sub sandwich or for the sweeter side, hand-spun milkshakes and classic sundaesthat make a fitting end to a day at Canaveral National Seashore. MoonLight not only offers the staples from their past, they have new sweet potato waffle fries, apple explosion sundae, an orange cream milkshake and more. They even take special requests. Drive-up or dine-in, they still offer carhop service as well as intirior seating restored with the classic diner décor and walls lined in nostalgia. | moonlightdrivein.com

Dino’s Drive-In
Winter Haven | Established 1968

Not too far from Orlando, just about an hour’s drive on I-4, you’ll find lovely Winter Haven, home to antique stores like Sherman’s Antiques, LEGOLAND’s Florida Resort, a wonderful theater group, and even a pontoon pub crawl. A stop in (or through) Winter Haven isn’t complete, however, without a trip to Dino’s Drive-In. Known for their large portions, reasonable prices and fantastic service, Dino’s boasts a steady flow of customers seven days a week. Dino’s offers carhop service reminiscent of the 1950s and 60s, but offers a more extensive menu. Regulars know to order the fried chicken, or the chicken livers if your so inclined. Crinkle cut fry fans will be stoked to know they’re considered some of the best in Polk County. | Too Cool For The Internet

Pappas Drive-In and Family Restaurant
New Smyrna Beach | Established 1970 

Pappas Drive-In and Family Restaurant, a beloved institution in New Smyrna Beach, has been serving hearty, delicious meals since 1970. Originating as a humble drive-in, it quickly won the hearts of locals and visitors alike, eventually evolving into a full-service family restaurant. The interior hasn’t changed much in 53 years, with its horseshoe counter of green stools offering guests a comfy seat and friendly surroundings. 

Pappas is renowned for its scrumptious American-style comfort food with Greek influences, a nod to the family’s heritage. Regulars rave about their signature chargrilled burgers, fluffy pancakes, and the famous Greek salad, bursting with flavor. The gyro platter, another favorite, features tender slices of seasoned lamb and beef, paired perfectly with tzatziki sauce. The history of Pappas is one of culinary passion and family tradition, reflecting in every dish served. 

Despite its growth and popularity, the restaurant has remained true to its roots, still offering the welcoming, nostalgic atmosphere that made it a fixture in the community. Pappas Drive-In and Family Restaurant continues to satiate the appetites and warm the hearts of all who dine there. | pappasdrivein.com

Mac’s Drive-Thru
Gainesville | Established 1987 

Glen McMillan opened Mac’s Drive-Thru in 1987 with his two sons, Jon and Ken. They brought with them a commitment to providing good-quality, fast-food prepared right. The team they have built and Jon’s dedication to a quality product is the reason Mac’s has been Gainesville’s favorite burger since its opening. No matter how you like your Burger -Mac’s Way (lettuce, tomato, onion, & mayo), All-the-Way (lettuce, tomato, onion, mayo, ketchup, mustard, pickle), or ketchup only -Mac’s makes it fresh and just the way you like it. From a hot ham & cheese to a chicken sandwich to a cheeseburger, every sandwich is made to order. The same can be said of their fries. Mac’s Drive-Thru is committed to keeping theMcMillan’s vision alive – a delicious and fresh product at a good price. Mac’s is a cash only establishment. | macs-drive-thru.com