Randy's Wooster St Pizza Naples

Randy's Wooster St Pizza Naples is a standout gem for pizza lovers visiting or living in Naples, Maine. Nestled conveniently on 770 Roosevelt Trail with scenic views of Brandy Pond, this vibrant pizza restaurant serves up an inviting blend of flavors and a warm, lively atmosphere that makes every visit memorable.

The menu at Randy's Wooster St Pizza is a delightful celebration of classic and inventive pizza creations, designed to satisfy a broad range of cravings. Whether you're drawn to the familiar comfort of a Large Cheese Pizza or the bold flavors of the Pepperoni Pizza or BBQ Chicken Pizza, each slice bursts with fresh, savory toppings, perfectly melted cheeses, and a crust that strikes the ideal balance between crispy and chewy. Unique offerings like the Olive This Pizza and Cheeseburger Pizza showcase Randy’s flair for creative, crave-worthy twists that invite repeat visits.

If you prefer to explore beyond pizza, their selection of hot grinders and quesadillas—such as the Chicken Parmesan Grinder and the Quesadilla Ala Nifla—delivers hearty, satisfying options. For lighter fare, the thoughtfully crafted salads, including the My Big Fat Greek Salad and the flavorful Buffalo Chicken Salad, offer fresh, crisp textures and vibrant tastes to balance your meal. Not to be missed are the Nashville Hot Chicken Wings, a fiery delight that regular guests rave about.

The dining experience at Randy's Wooster St Pizza goes beyond the food. Customers frequently highlight the friendly, welcoming vibe from the moment they arrive. The staff’s genuine warmth, from the cheerful greetings at the door to attentive service during meals, transforms a simple pizza night into a truly enjoyable outing. The inviting interior buzzes with a fun yet relaxed energy, while the option to sit outside during warmer months allows guests to savor their meal with a beautiful lakefront backdrop.

Real guest reviews underscore the authenticity and charm of Randy’s. Stephen B affectionately calls it his "favorite pizza place in Naples," appreciating not just the great pizza but also the laid-back, boat-friendly summer vibe. Newcomers and locals alike praise the consistently delicious food and quick service. Lost Aviators were thrilled with their first visit, citing excellent pizza and standout service from staff member Kate. Matthew Carter’s first experience, after years of proximity, left him impressed with both the creative menu and the friendly team that makes every visit feel special.

Whether you're craving perfectly baked, bubbling hot pizza with inventive toppings or a satisfying salad or grinder, Randy's Wooster St Pizza Naples delivers a rich culinary experience paired with hometown hospitality. It’s the kind of place that invites you to linger over your meal, share laughter, and plan your next visit.

For a pizza spot that blends authentic flavors, generous portions, and a welcoming atmosphere right on the main strip and by the water, Randy’s Wooster St Pizza Naples is a must-visit destination in the area.