Fast forward ten years, Harry and his brother Al opened a new restaurant, Harry’s Prohibition Bistro, in 2013. Unlike the diner, the Bistro is themed after another of Harry’s favorite eras – the Prohibition era and the Roaring Twenties. The 1920s vibe is evident from the moment you walk through the door. The red velvet curtains and yellow glow of the lamp wall sconces, 
the old-fashioned street clock right in the middle of the dining room floor, the staff in their red fedoras…. you’re transported to a former time. Taking advantage of the fact that we are no longer under the restrictions of Prohibition, the Bistro has an impressive wine list and bourbon selection. On the cocktail menu you’ll find period classics like the Gin & Jam.
The food menu at Prohibition Bistro consists of a large selection of pizza and pasta, but their specialty is their authentic wood-fired, VPN Certified, Neapolitan pizza. VPN stands for pizza that has been certified by the Associazione Verace Pizza Naptoletana, an Italian organization that establishes and enforces strict, traditional rules for making authentic Neapolitan pizza. It ensures that pizzas are made with specific ingredients like type "00" flour and San Marzano tomatoes, hand-stretched dough, and cooked in a wood-fired oven at high temperatures for a short time. Prohibition Bistro sources their flour and Bufala mozzarella from Italy and most of the other products and produce are sourced locally. For two years Harry experimented with a hand-built wood-fired pizza oven in his backyard, working to get the temperature just right – 900 degrees to be exact.
Prohibition Bistro is now owned by Harry’s son Adrian. Adrian grew up in his grandparent’s restaurant, Ray’s Family Restaurant in Chicago, which they owned for almost 40 years. Adrian would visit his dad in Sheboygan every weekend and help out at the diner and eventually ended up moving to Sheboygan himself.
After finishing high school, Adrian actually aspired to join the military or become a police officer but ultimately realized that he had a good palate, with a passion for cooking and for healthy food, leading him to pursue the culinary arts. He attended culinary school in Madison for two years, working in two different VPN-certified restaurants, as well as another Italian Pizzeria while he was there, gaining valuable training and experience. After graduating in 2016 Adrian was involved in every aspect of running Prohibition Bistro from bartending, working in the kitchen, and making the food to dishwashing, hosting and even cleaning. Even today he can often be seen outside piling the wood they use for the pizza oven. In 2019, Adrian completed the Full Immersion Course at Roman Pizza Academy in Miami. He is one of only two chefs in Wisconsin (the other being his uncle Al) to be certified in Roman al taglio pizza.
Eventually Adrian dreamed of owning his own restaurant and began looking for opportunities in Sheboygan. He looked at numerous prospects that didn’t work out for one reason or another. Meanwhile, Harry and his brother Al were burning the candle at both ends trying to run their diners during the day and the Bistro in the evening. In 2023, Harry and Al decided to sell Harry’s Prohibition Bistro to Adrian, fulfilling his dream of owning a restaurant in the very place he had spent so much time and poured so much of his heart and soul into.
When asked what inspires him, Adrian said it is his love of food. Growing up in restaurants and diners, he developed a passion for food and creating something, which is evidenced by the creative variety of items on the menu at Harry’s Prohibition Bistro (I see you, Corn Pizza!). He said his biggest challenge is probably the business management details and staying on top of the administrative things. Another challenge is training kitchen staff on the art form of cooking their pizza the proper way, working with a live fire, knowing when to put wood in, at what point to put the pizza in, etc.
I asked Adrian what his favorite dish is on the menu, and this turned out to be probably the hardest question I asked him. He ended up going with one pasta and one pizza. For pasta, the Spicy Chipotle with shrimp. The pizza was really a challenge to choose just one. He said he would go with the Peppadew but substitute the ham for hot sopressata (a spicy salami).
I was anxious to try Adrian’s pizza choice, so I ended up going home with a Peppadew with hot sopressata. My honest review? It had SO much flavor but be prepared for a little heat! The peppadew pepper is very unparalleled. It offers a tangy, sweet, and spicy burst of flavor all at once. The hot sopressata is sliced remarkably thin and had the perfect amount of crispness from the oven, but it definitely brought the heat factor up a few notches – whew! If I were to get this one again, I would ask them to go light on the hot sopressata.
I have had the chance to try many of their pizzas over the years, including the Margherita, Lemon, Marsala Beef, Mezza Luna, Peppadew, Truffle, and Corn Pizza. The Lemon Pizza and Corn Pizza are probably the most unique, and I absolutely recommend stepping out of your comfort zone and giving them a try. My favorite appetizer is the Foccacia Fritter. Don’t forget dessert! The house-made tiramisu is excellent. I have also tried the Camp Fire Pizza, but this is one you’ll want to share with a group. It’s a full-size pizza topped with delectable goodness: Nutella and toasted marshmallows. Yum.
At Harry’s Prohibition Bistro, there’s not a bad seat in the house. The outdoor patio offers stunning river views, and part of the patio is enclosed and heated for those chilly evenings. I have even sat out there in the middle of winter, and it’s toasty warm. The inside offers dim, moody Prohibition-era lighting, giving off cozy, romantic vibes. You can’t go wrong either way, but I personally love sitting on the patio. In the summer, it’s so picturesque watching boats and people go by. In the winter, the lights reflecting on the water present an enchanting view.
