31 Best Italian Restaurants near Winter Garden

“My favorite restaurant in Winter Garden. Decided to do Italian for Thanksgiving and it was outstanding. My favorite is their Pork Osso Bucco and they did not disappoint. Service and owners are always on point. Thank you for enjoying my first Thanksgiving being waited on. Always recommend this place, never a bad meal. Thank you Dorina“

“This was our first time but it won't be our last. They were very accommodating with Gluten free options like GF pasta and GF bread. They also offered to make almost any entre GF.

The service was EXCELLENT!! Antonio and Josephine were amazing hosts. They really made you feel welcomed and were happy to answer questions about the menu.

We had the shrimp scampi and it was delicious with plenty of jumbo shrimp. This came with rainbow carrots and broccolini.
We also had the Filet Mignon with mashed potatoes and vegetable. The food was prepared exactly how we wanted and seasoned to perfection.

We had the house Tri-Mozzarella platter appetizer and it was amazing!!

We had an excellent meal and great experience!!!
We definitely recommend this restaurant!

Dietary restrictions: Gluten free options available such as pasta and GF bread. They also are very accommodating in offering to prepare almost any entre GF!!

Parking: Huge parking lot.

Kid-friendliness: High chairs available.“

“Huge RAVE for La Piccolina - Winter Garden. We went to celebrate my father’s birthday and everything was wonderful. The food was delicious, so flavorful and generous portions! On top of our delicious meals the service was excellent! They went above and beyond, surprised my daughter with a fun make her own pizza, which was so fun and a sweet surprise. This place is authentic and caters to hospitality! Thank you for making our dining experience so wonderful! We can’t wait to come back.“

“The best pasta I have ever tried! On top of that it’s the customer service you receive whenever you make an order or go to the markets. A company with true customer loyalty with the best fresh pasta at its heart.“

“Sue and I have not been to this place since they converted to sit-down and order. Finally joining the real restaurant world. We have eaten here about 20 times in the last few years and have always enjoyed the food, but felt strange with the get-your-own-drink aspect of it. Anyways, we are seated at our favorite booth, Perry Como, Elvis, Dean Martin, and Sinatra (the usual suspects) crooning at a comfortable level, with decent speakers. Oscar greeted us and took our drinks order, leaving a couple of rather impressive menus with us. We spent some time looking at the menu, as the format has changed somewhat. I ordered the shrimp marsala on linguine, Sue ordered the same on some other pasta noodle (You choose). After a reasonable interval, our food arrived. 2 huge bowls of deliciousness thick enough that it could have been called a stew. Lrt me tell you, I've been to restaurants that the orders contained little meat, little mushrooms, and a LOT of broth. Not here! These bowls were crammed with a ton of food. Shrimp, portobella mushrooms and pasta that was not overcooked. I gotta tell you, Sue and I dine out a LOT...various venues all over WG/Ocoee/Windermere/Clermont. This was probably the finest meal I ever had. The improvements the restaurant made are A+ Definitely worth dropping a hundy on.“

“My sister and I had our first visit to Cariera's in Winter Garden, FL, a family owned restaurant, for lunch about a week ago. I first heard about it a few years ago on the NextDoor App for the Dr. Phillips neighborhood in Orlando, which I believe was their original location. We grabbed the menus, sat at a booth, made our selections and then went up to very friendly Cashier/Waitress Valerie to prepay our meals and tips. I had the Fried Calamari, Shrimp & Crab Ravioli ala Vodka, fruit infused red sangria and for dessert, Limoncello cake. Sis had the Lasagna. Everything was delicious (see pics)! The calamari was seasoned crispy on the outside but light and tender on the inside. The ravioli didn't have as much crab as I would have liked but plenty of shrimp. The vodka sauce was creamy and cheesy. Even the garlic roll was fresh and warm. Everything was perfect and there was plenty leftovers to feed us a couple more days. The owner and Valerie and other servers checked on us periodically throughout our meal. The food, welcoming atmosphere and excellent customer service provided our first-time visit with a very happy, delightful experience! There are plenty of veggie and vegetarian options and a $10 'Little Bambinos' menu. Cariera's is located in a strip mall with plenty of parking except handicapped spaces are limited. We plan to return to try different things on the menu and would highly recommend for indoor and/or carry out meals with family, friends and visitors.“

“Local Gem We live a 15 minute stroll from Mangoni's Italian Market, but at "feels like" temps hovering around 105°, strolling to lunch hasn't been as attractive ? Sunday, hubby wanted a relaxing lunch with sangria! So, we drove (& charged our EV in the parking garage). We had the entire patio to ourselves, as diners likely expected unbearable heat. Mangoni's pergola and great ceiling fans made patio dining the experience we wanted---even when the afternoon storm blew up from the west, we were protected from rain. We enjoyed our favorite, GF goat cheese pizza, with our sangria. Unlike most places, Mangoni's GF crust is an excellent, thin cauliflower crust. And, it’s not an upcharge. We also enjoyed meeting Georgia, the regional manager, who chatted with us about the social hour (11-6pm weekdays). She made a GF garlicky cheesy Flatbread for us to try--now we have more reason to stroll (or drive) over! Oh, and take away is a frequent option. Really, Mangoni's is a local gem.“

“The service is always friendly. Our oldest started going as an infant and she loves all the pasta dishes and the pizza. We decided to skip the long wait times at the restaurants closer to the shopping areas. Far more relaxing!“

“We always enjoy lunch at this I-Drive location. The food is delicious and May, our server, is always amazing. May is extremely attentive and personable. Good job Carrabbas and May! Can’t wait to go back.“

“I stopped by because I could smell how good the food was walking to Publix, Jay helped me find a perfect late night meal.He is the kindest person and understands the menu and its pairing very well! Jay provided excellent recommendations and you can tell he genuinely cares for customers and its elevated the dining experience. i’d highly recommend this restaurant!“

“Great food and great service“

“Beautiful hidden gem! The service is top notch, from the hostess, to the multiple servers to the accordion player. Very attentive and genuinely seemed happy to be working at Crostini’s. We got one of the fish specials, and a Veal Parmesan, which they are known for. The martini’s are delectable, and the dessert is out of this world. A must try if you’re anywhere near the Orlando area.“

“I recently had the pleasure of dining at Maggiano's Little Italy in Orlando on International Drive and it was an experience worth sharing. From the moment we walked in, we were greeted warmly by the hostess, who promptly seated us at a cozy table that perfectly set the tone for the evening. The waitstaff was exceptional—attentive, friendly, and knowledgeable. They made sure our glasses were never empty and checked in just the right amount to ensure we had everything we needed without being intrusive. For the main course, we chose the Chicken Parmesan, which was cooked to perfection with a crispy exterior and tender, juicy chicken inside. The pasta was al dente, and the meat sauce was rich and savory. It was really enough for two people to share. To top it all off, they brought two plates of their famous lemon cookies to our table, to celebrate our third anniversary. Overall, our experience at Maggiano's was nothing short of excellent. The combination of outstanding service, a welcoming atmosphere, and delicious food made for a memorable evening. I highly recommend Maggiano's for anyone looking to enjoy a wonderful Italian meal with top-notch service.“

“Visited Orlando for the weekend golfing at Bay Hill. Fresco's was recommended by the folks at the Lodge. Glad we stopped in for dinner. The food is excellent. It will be my goto on future Orlando visits.“

“Fantastic food and friendly but professional staff. We had tiramisu and wine one night and then the meatball appetizer and lobster ravioli the following night. All was delicious but the meatballs with the polenta was a delicious new twist.“

“Delicious food, very attentive service.

Kid-friendliness: Yes, there are tablets that play games for children on the tables, which despite not being free, are a good alternative to entertain the little ones, there is also a Kids menu

Wheelchair accessibility: The two units I visited are accessible“

“Good food, fast service !“

“Amazing setting, music, and food. Everything is very presentable, and fresh.“

“Food: 5- I save this number for the cream of the crop. I do not normally get gnocchi because my best friend’s dad is from Italy and homemade is amazing. I tried theirs and it did not disappoint. My husband had the steak, another prime find. Our friend had the spaghetti and wanted a second serving.
Service: 4- Very nice and the music was great.
All in all: 5- I never give a straight 5 rating but well earned!“

“Everything was spectacular. My family shared an order of suppli and a margherita pizza. Reminded us of our vacation to Rome. Our entrees were authentic and delicious. The wine suggestions were excellent. All the servers are knowledgeable, attentive, and hilarious! It was a perfect evening.“

“Love this place… perfect combination of atmosphere and great food.“

“We had a wedding shower Bella Tuscany in Ocoee on Sunday. The room was the perfect size, the food was outstanding (we did a brunch), and the service was amazing. A big shout out to Barb and her staff who helped us make the shower so memorable.“

“This is the best true Italian food in Orlando. Reasonable priced, great selection, family atmosphere. You get a little taste of Italy right here in Apopka.“

“I have no idea what the people who rated this establishment lower are talking about. The service, food, atmosphere and general ambiance were exceptional. After dining in some of the higher end resort hotels in Disney this Universal treat beats them hands down. Even with the construction maze one has to navigate that may detract a bit one must remember it is not the fault of the restaurant and they more than make up for this slight inconvenience by their service.“

“Best eggplant parm I've ever had. Castello's is my new favorite restaurant. The young man who waited on us and the female chef were very polite and thanked us for coming in.“

“I love this Restaurant, the Alfredo pasta is Amazon, love forever Oreganatta“

“Delicious and fresh!!! A neighborhood treasure!!!“

“Their are clearly mark take out and delivery. Do you feel the same way when you go papa johns or Dominos and there is no sitting.“

“I have written a review on Calabria Ristorante in the past. Nothing has changed the food is always delicious as are the Martini's and other drinks. This post is not just about food, but a WONDERFUL WAITRESS NAMED CHRISTA G. SHE'S THE BEST! We have had her wait on us at least 3 times. She is attentive, and has a fantastic disposition. Her smile tells us she likes her job. Our friends like extra sauce and extra Parmigiano on thier chicken cutlet dinner. I try different menu items as I will try anything. I have never made a bad choice. My wife likes the Calamari, the Greek salad etc. CHRISTA ALWAYS BRINGS THE RIGHT MEAL. Try the Italian Margarita, you're gonna love it. If I could make one suggestion, people come in for special occasions. Birthdays etc. the restaurant should help in the celebration with a piece of cake and a candle or maybe a piece of Tiramisu and a candle. A happy whatever the occasion may be can be done by a server. That little touch goes a long way! Lastly the Manager needs to walk around to make sure all diners are content. I worked in the service industry for 12 years. The personal touch makes customers happy. Peace, Ralph Michael“

“Last night my boyfriend and I made a last minute decision to eat here. I joined the waitlist on my phone and within 10 minutes got the text to see the host (not bad!) we immediately went in and noticed there was no hostess at the front. It was busy so we didn’t mind waiting a little bit. 5 mins go by and a lady who looked overwhelmed came over and asked for our info and told us it would be 20 mins. We told her we already were on the wait list and got the text. She said we didn’t come fast enough so they gave away our table. Confused and a little annoyed, I quickly said we just got the text and came straight over and were waiting for someone to help us. She immediately apologized, cleaned off a table and sat us. She apologized for the way everyone was a bit all over the place and said she would be helping the server tonight. She grabbed our drinks and our waitress comes by and greets us explaining they were unexpectedly down 5 servers and trying to cover multiple sections. As a server, I apologized that she was going through that and told her to take her time that we weren’t in any sort of rush. For as busy as it was with little amount of servers, she with the help of a few others were on top of it and we didn’t wait long at all. We were in and out in about an hour and a half (since we weren’t rushing to leave anyway). Thank you so much for everyone’s professionalism and hospitality. You guys rocked during a crazy and stressful situation! I wish I remembered my servers name because I would love to have her as my server again!“

“Celebrated our 31st with dinner here. Christine was an amazing server. From her recommendations, to her absolutely effervescent personality, she was the icing on a delicious and extremely satisfying meal. Planning to return tomorrow to try something else on the menu, as tonight's meal was amazing.“