Kappy’s Subs in Maitland is a Step Back in Time

During the Great Depression, restaurant owners began to use retired train cars as micro-cafes. These cars were only big enough for a grill top and two staff members. A long bar with stools was the only seating. This became the prototypical vision of the American diner.

Arthur Valentine started as a restaurant operator in Kansas but became the frontman behind sales of prefabricated diners in the 1930s. They were initially manufactured by the Ablah Hotel Supply Company. After World War II, this company became Valentine Manufacturing, Inc. and sold units nationwide. They became known as Valentine Diners. Few survive today, but one of them is Kappy’s Subs in Maitland!

The diner is located at the corner of US 17-92 and Sybelia Avenue. It opened as a What-a-Burger in 1963. They offered drive-up car service, where car hops would visit you at your car window, take your order, and bring out your food. It operated under this model for several years until the burger joint closed.

Then, in 1967, Isodore “Itch” P. and Anne M. Kaplan purchased it and opened it as Kappy’s Submarine Sandwiches. Isodore continued to offer burgers but added several menu items. They sold hotdogs, which they proudly proclaimed they had shipped in from New York daily. They offered toppings like in-house brined sour kraut and an old Greek recipe for the chili sauce. They became best known for their various submarine sandwiches, all made to order, including their Italian sausage and Philly cheesesteak subs.

Anne and Isodore Kaplan
1968 Ad in the Orlando Sentinel with their full menu

The Kaplan’s offered the classic diner bar service with swivel stools. They added a large outdoor patio with picnic tables to enable more people to dine in without eating in their cars. Maitland was a sleepy little town back then, but they encouraged people to call ahead and swing by to pick up lunch on their way north to the beach.

Now, obviously, “Kappy’s” is named after the “Kaplan” family. However, by 1973, they were ready to move on from running the diner. One day, a man from New Jersey strolled into the restaurant. He was lured by the sign hawking the fresh from New York foot-long hotdogs. The customer, who moved to the area a year earlier, had worked in a similar business since he was a kid. His dad owned a similar sub-shop in Atlantic City. The two started a conversation about the business, and one thing led to another… the Jersey boy bought the place!

Bob Caplan in 1985

Conveniently enough, the man’s name was Warren Robert “Bob” Caplan–yes, like Kaplan but with a “C.” Bob and Claudia Ann Caplan took over the business in 1974. They wisely chose not to rename it “Cappy’s Subs” and kept the katchy “K” in the name.

Besides a couple of new menu items and replacing the fryer and grill, not much has changed since then. It still remains in the Caplan family, and they feel a duty to the community to continue it. Bob retired in 2008, and since then, it has been run by his daughter, Rachel Milsom of Altamonte Springs. They’ve also put the third generation, Adam and Maya, to work in the shop.

When you go to Kappy’s, it really is like stepping back in time. It is one of those places that seems frozen from a Back to the Future movie or something. Generations of loyal customers continue to visit them for the food and the romance of a place like this.

Your adventure starts by battling for a place to park. The place is always hopping, and its anemic parking lot backs up to the railroad tracks not far from the Maitland SunRail. You place your order from a window, find a place at the bar or picnic table, or wait in your car for them to call your name. There are no frills, but there are great fresh-made sandwiches, burgers, hotdogs, chicken tenders, milkshakes, giant sodas, onion rings, and fries. The cheesesteak with peppers and onions is my favorite!

The restaurant’s mascot is named Sammy Sub. The cartoon boy, holding a “super sub” sandwich, is a carry-over from Bob’s dad’s restaurant in Atlantic City. You’ll want to peek at their throwback signs and maybe even pick up one of their shirts to commemorate your visit.

Kappy’s is open seven days a week. They have also expanded to offer catering services and a food truck at special events. After you stop by, if you’re during the citrus season, stop by Hollianna Groves across the highway for another throwback experience.


  • Monday – Friday:8:00 am – 9:00 pm
  • Saturday:10:30 am – 9:00 pm
  • Sunday:11:00 am – 4:00 pm

Visit Kappy’s


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