Chesapeake, Virginia’s pizza landscape blends coastal tradition, suburban comfort, and melting-pot creativity.
The best pizzerias offer everything from East Coast authenticity to gourmet brick-oven and hearty family-style pies. Here are Chesapeake’s top five for 2025.
1. Chesapeake Pizza
Locally owned and operated since the ‘70s, Chesapeake Pizza is a neighborhood legend—famous for its sweet red sauce, thick, chewy crust, and old-school atmosphere.
The specialty “Chesapeake Super” and classic pepperoni pies are city staples.
Their friendly service, big booths, and community spirit keep generations returning.
2. Reginella’s Italian Ristorante
A taste of Naples in Coastal Virginia, Reginella’s features wood-fired Neapolitan pies with bubbly charred crusts, imported ingredients, and creative toppings.
From a perfect Margherita to seafood-topped specials, it’s equally ideal for date nights and family gatherings.
The antipasti and pastas are crowd favorites, too.
3. Ynot Italian
A beloved regional chain, Ynot puts out hand-tossed pizzas with golden crusts and both classic and creative toppings—try the White Spinach or the loaded “Ynot Special.”
With a full menu of pastas, subs, salads, and desserts, as well as gluten-free options, Ynot is a family-friendly Chesapeake go-to.
4. Leonardo’s Pizza & Subs
This spot is a favorite for giant slices, fast delivery, and excellent value. Leonardo’s dishes out New York–style pies, garlic knots, and towering Italian subs.
Their “Meat Lovers” and “Hawaiian” are especially popular, and the speedy service makes it perfect for busy nights.
5. Brooklyn Pizza
Lauded for authentic NY-style pizza, Brooklyn Pizza’s thin, crisp-yet-foldable slices transport you straight to the Big Apple. Classic cheese, “Grandma Pie,” and white pizza are regulars’ favorites.
The humble, counter-serve spot is known for quick carryout and friendly staff.
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