Leonardo’s Pizzeria

OK, so there is a big Italian population in Gloucester. I come from a big Italian family. Granted, Leonardo’s doesn’t look like much from the outside. Get over it and walk in and I promise you won’t be disappointed. You walk in and it looks like a standard pizza/​sub place, but if you are dinning in you can get a couple of dinner menus and sit in the dinning area to the side. I kid you not, some of the best Italian food I’ve had and the prices? Forget about it! It’s so affordable to get gigantic portions of good food and feed an entire army which we had with our group of 12. The sauce is more sweet than spicy and when you ask for a sausage on the side you get three. Ridiculous! One in our group got a small calzone which was about the size of a regular pizza. Get over the exterior and walk into the best secret in Gloucester.

While I thought the food was good, this place is overpriced, no air conditioning and long waits for food. I would have been better off going to Sebastians Marias or Halibut Point for an air conditioned sit down meal with wait staff for the same or less. Even Azorean is priced better and have a great selection of dishes for all paletes. I hate overpaying for mediocre. Is there no pride in quality and taste anymore? Fine if you’re a wealthy tourist but for a middle class working family it doesn’t fly. And my pasta eggplant and my husband’s homemade pizza would rock your socks off!

Used to be my salad «go to» place. Shortly, after changing hands, things changed a bit. Last time I went, the romaine was clearly unwashed and dirt was visible in the white ribs — yuck! Also, counter staff seems to be a bit — stressed — and forgetful. Have not been back since…

I absolutely LOVE Leonardo’s. Their burgers, subs, wraps, pasta dishes. All fabulous and always a good sized portion of food.

I have no idea how these places stay in business. Disappointing and expensive pizza… why?

I love the steak tip salads here, they also have my favorite pastry baklava so I get a treat when I do go in. You won’t be disappointed when you try this place.

their takeout pizza is good. went in today for lunch and got a tuna sub with lettuce, tomatoes, and ‘hots’. they use way too much mayo in their tuna salad and a paltry amount of wilted shredded lettuce and tomatoes. i shall stick to their pizza from now on.

It feels so nice to go to a family run business. They’re so welcoming, kind, and personable. Great food and great service.

I use to go to Leonardo’s for their take out years ago while we would visit. Just picked up two dinners tonight and was very disappointed. The quality just wasn’t there.

Now under new ownership.
If you are going to keep the same name, keep the quality
and quantity.
Suggest going back to the original menu if they plan on succeeding.

Since new ownership has taken over, the food and service have gone downhill while the prices skyrocketed! I use to take my family here every Friday night for over 15 years! The quality was consistency far superior to anything around. The change in the red sauce was a big mistake! I would even pay their crazy prices for the old recipes. I’m sorry, but almost $ 20 for one ham and cheese calzone? I don’t think so! Disney world has better prices! The waitstaff was far more interested in talking with their boyfriends than helping us. Granted, the times that happened, it was close to closing time.
If you are looking for a sub or salad, they are great. Other than that, go to Maria’s. It kills me to say that, too.

Leonardo’s is a small family-​owned pizzeria/​sub/​Italian food shop on downtown Gloucester’s Main St so it’s metered street parking. Friendly, very casual, & BYOB. Their prices are reasonable. Their slices of pizza are pretty good, but only available till 1PM. The sauce on their pizza is sweet & tangy. The cheese is a little oily, but plentiful. And the crust is thick, chewy, & dusted w/​semolina.
They have a wide variety of subs & pasta dishes. Their pasta Alfredo was somewhat gummy. I’ve heard they prepare things that are not even on the menu! Eat-​in, take-​out, & delivery.

These friendly folks make the BEST grilled chicken Caesar salad that I’ve ever had. So much so that it’s the only thing I’ve ever gotten there for take-​out! When I feel like «treating myself» at lunchtime, I leave my office and head over to Leonardo’s for one of their fabulous Grilled Chicken Caesars!!!

I really feel like Leonardo’s is the forgotten pizzeria and sub shop in downtown Gloucester. You hear people rave about Valentino’s and Virgilios but not many ever say Leonardo’s as a first choice, and that’s too bad. The food is pretty good, and the service is top notch.
The food is what you’d normally find in a pizzeria and sub shop– pizza, subs, salads, small dinners (usually fried or with roast beef). The restaurant is located in the eastern end of downtown, so parking is on the street. Unless something special is happening downtown, you’re sure to find parking within walking distance (if not directly outside of the store).
If you want a quick bite to eat, this may be the place for you as it doesn’t get as crowded as other downtown locations. One thing to note– they don’t serve pasta dishes until dinner. I was really disappointed because my friend recommended the ziti dish and I walked down, but no luck since it was lunch time.
Try out this hidden pizzeria and let me know what you think!

You can tell that Leonardo’s is onto a good thing when their seated dinner crowd are mostly local Sicilians eating pasta dishes. Gloucester Sicilians eating pasta dishes at a restaurant is a rare thing to witness and telling. (This probably means either their stove at home blew-​up or their Grandma died.)
Anyway, it’s really a pizza/​sub shop by look and feel — but they put a little extra into it and have some exceptional menu items. I usually go for lunch and order one of two items.
The Chicken Kebab Salad w/​Feta is huge and amazing simply for Leonardo’s trademark juicy marinated chicken which is grilled perfectly and goes great upon the bed of fresh crisp veggies.
The other lunch fave is the Meatball Sub which is put into overdrive from the homemade tomato sauce –made daily says Lenny, the proud owner. I’m sure the sauce (fresh, tangy, and a touch of sweetness) is part of the appeal for the evening pasta crowd too. Oh, the meatballs are juicy and tasty and ask for extra provolone for true sensory overload.
Yeah, you can order a decent pizza here, but save the pizza order for Maria’s or Sebastian’s. You want to be ordering one of Leonardo’s salads, hot subs, or pasta dishes. And if you do it enough, Lenny will remember your name as he does with hundreds of his regulars.

Good solid food, no real complaints on this one other than they are closed on Sundays.
This is a standard sub shop during the day with a line out the door at lunch cranks out the best chicken kabob sub I’ve ever had. It seems like everybody else feels that way too because I’m pretty sure they have one grill devoted to just chicken during lunch hours.
At night they have dinner service with pretty much the same menu as lunch but the wait on you. Everything here is homemade and you can tell when you bite into the lasagna or meatballs that the people running the place love what they do. You can also BYOB and I’ve found that Lenny (owner) has no problem taking any unwanted beers off your hands when you leave.
About the owners, they are some of the nicest people you will every meet. They are from Gloucester and their kids go to Gloucester schools. Everybody that works for them is very friendly and you never feel like you are in a rush.

BEST ANTIPASTO SALAD THIS SIDE OF THE MASON-​DIXON LINE, AND THE OTHER SIDE OF THE MASON-​DIXON LINE.
why do i like random italian meats on my salad? i don’t know but i friggin like it, and leonardo’s is the only place in my heart of hearts that wins my love. i don’t know what they do any different than anyone else. i don’t know if the meat is a better quality, cause i don’t like these meats other than on top of a salad (to the point where i cringe a little at the thought of a mortadella sandwich). i think it’s just that it’s made with a loving hand.
leonardo’s is great for everything else, too. i’ve heard they have amazing pasta dishes. i’ve gotten a few different subs and i’ve never been disappointed. when you pick up your order you’re treated like a friend of the family.
i miss the crap out of leonardo’s, for sure. i’m on a quest for a good antipasto salad in salem and so far, no dice. i know gloucester isn’t far away, but it’s too far when you’re just picking up subs/​salads. if i’m spending any amount of time in gloucester and my family is not feeding me, i’ll absolutely be picking me up some antipasto love.