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Best Italian Restaurants in Charleswood

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19 restaurants available nearby

A photo of Alena Rustic Italian restaurant
4.8
Exceptional(628)
Price: Expensive
• Italian • Winnipeg
Booked 13 times today
Coming Soon!
A photo of Pizzeria Gusto restaurant
4.6
Exceptional(1839)
Price: Expensive
• Italian • Academy Road
Booked 31 times today
Pizzeria Gusto on Academy Road in Winnipeg is a delightful destination for dessert enthusiasts. Known for its warm ambiance and exceptional service, this beloved eatery also garners rave reviews for its dessert offerings. Diners often highlight the "perfect Affogato" as a must-try, with its exquisite balance of flavors and textures providing a sublime finish to any meal. The restaurant’s dedication to quality is evident in their use of authentic Italian ingredients, ensuring each dessert is a genuine treat. With such glowing feedback, Pizzeria Gusto promises an unforgettable dessert experience that will have you coming back for more.
A photo of Cafe Carlo restaurant
4.7
Exceptional(2593)
Price: Expensive
• Italian • Little Italy/Corydon Village
Booked 21 times today
Cafe Carlo, nestled in Winnipeg's charming Little Italy/Corydon Village, offers a vibrant Fusion/Eclectic dining experience that delights both locals and visitors. Known for its "consistently great" food and "superb service," this neighborhood gem skillfully marries world flavors with an Italian flair, creating dishes that are both "classic and modern." Standout creations like the famous Fett Chile and flavorful seafood chowder have earned rave reviews, with diners praising them as "out of this world" and "scrumptious." The restaurant's warm, cozy atmosphere and personable staff ensure that every visit is memorable, making Cafe Carlo a "perennial favorite" for its eclectic culinary adventures.
A photo of Boston Pizza - Birchwood restaurant
4.4
Awesome(6)
Price: Moderate
• Italian • Birchwood/Silver Heights
Boston Pizza is a family restaurant and sports bar with great food, like pizza, pasta, wings, and more!
A photo of Boston Pizza - Kenaston restaurant
4.3
Awesome(6)
Price: Moderate
• Italian • Southwest Winnipeg
Boston Pizza is a family restaurant and sports bar with great food, like pizza, pasta, wings, and more!
A photo of Boston Pizza - Grant Park restaurant
4.3
Awesome(6)
Price: Moderate
• Italian • Grant Park
Booked 1 time today
Boston Pizza is a family restaurant and sports bar with great food, like pizza, pasta, wings, and more!
A photo of Boston Pizza - Polo Park restaurant
4.3
Awesome(3)
Price: Moderate
• Italian • Polo Park
Boston Pizza is a family restaurant and sports bar with great food, like pizza, pasta, wings, and more!
A photo of Cibo Waterfront Cafe restaurant
4.7
Exceptional(2105)
Price: Expensive
• Italian • Exchange District
Booked 26 times today
Cibo Waterfront Cafe in Winnipeg's vibrant Exchange District offers an exceptional Mediterranean dining experience, celebrated for its authenticity and quality. Nestled along the iconic Red River, diners are treated to stunning views while enjoying a diverse menu crafted from scratch, featuring hand-stretched pizzas and "innovative takes on bruschetta" that leave tastebuds delighted. The "drunken mushroom pizza" and "pear and prosciutto" options receive rave reviews, described as "fantastic" and "phenomenal." The chic ambiance, coupled with "gracious service," creates a welcoming atmosphere for any occasion. Whether for a cozy night out or a pre-theatre dinner, Cibo's Mediterranean cuisine promises a memorable experience.
A photo of Gusto North restaurant
4.3
Awesome(452)
Price: Moderate
• Italian • South Portage
Booked 21 times today
Gusto North in South Portage, Winnipeg, is a haven for Pizza Bar enthusiasts seeking authentic Italian flavors. This charming spot, inspired by its original location on Academy Road, delivers a genuine experience akin to dining at an Italian family table. Diners rave about the "great pizza" and the "fantastic food," consistently praising the "delicious food" and "wonderful service" that makes every visit memorable. The vibrant atmosphere, combined with a meticulously curated menu, ensures that every pizza served is a slice of perfection. Whether it's a casual lunch or a romantic dinner, Gusto North promises an unforgettable culinary journey.
A photo of Vida Cucina Italia at The Fort Garry Hotel restaurant
4.7
Exceptional(197)
Price: Very Expensive
• Italian • Winnipeg
Booked 8 times today
Vida Cucina Italia at The Fort Garry Hotel, nestled in the heart of Winnipeg, offers an unparalleled Contemporary Italian dining experience. Helmed by Italy's culinary virtuoso, Chef Rosanna Marziale, and Resident Chef Fabrizio Rossi, the restaurant masterfully fuses traditional Italian recipes with a modern twist. Diners rave about the "authentic Italian homemade pasta and bread," and the exquisite "sea bass carpaccio is not to be missed." The ambiance is both "quiet and intimate," perfect for special occasions. Praised for its "fantastic service" and "exceptional wine pairings," Vida Cucina Italia is a must-visit for those seeking the finest Italian cuisine.
‘About the restaurant’ descriptions have been generated using an artificial intelligence model comprised of OpenTable proprietary data that has not been independently verified by OpenTable. The content is presented as-is, for informational purposes only.

See what locals rave about

From verified diners like you
From verified diners like you
  • Shannon
    Winnipeg / Manitoba •6 reviews
    5.0
    Dined 1 day ago
    Consistently amazing food-no complaints and satisfaction above and beyond expectations!
    More info
    Cafe CarloPrice: Expensive• Italian• Little Italy/Corydon Village
    4.7
  • Katherine
    Winnipeg / Manitoba •6 reviews
    4.0
    Dined on Jan 3, 2025
    Tvs are a bit too large and loud for my taste, but the food was great and pretty reasonable, and our server was fabulous.
    More info
    Boston Pizza - BirchwoodPrice: Moderate• Pizzeria• Birchwood/Silver Heights
    4.4
  • Sue
    Winnipeg / Manitoba •1 review
    5.0
    Dined on Jan 2, 2025
    The dinner and service were excellent. I have been to the restaurant several times and every meal has been very good. The prices are as well-they are not exorbitant. The only change I would like to see is Spanish wine on the wine list.
    More info
    Alena Rustic ItalianPrice: Expensive• Italian• Winnipeg
    4.8
  • KarenVIP
    Phoenix / Arizona •13 reviews
    5.0
    Dined on Dec 21, 2024
    Incredible teamwork shown by all to ensure smooth, timely, and friendly service during a full capacity setting. Super impressive! The changing cocktail options are always innovative and delicious, and they capture the season in a glass. The food consistently offers interesting combinations whose profiles work beautifully through each bite. Ending it all with the most perfect Affogato, you have yourself a most enjoyable meal in a lively and most welcoming atmosphere. Thank you all at PG!
    More info
    Pizzeria GustoPrice: Expensive• Pizzeria• Academy Road
    4.6
  • Tammy
    Winnipeg / Manitoba •5 reviews
    4.0
    Dined on Oct 19, 2024
    We enjoyed the visit seemed they were short staffed on waitresses . Ours came by as much as she could but there was a time we sat waited for anyone to walk by to get water we found a different waitress and she got a younger girl to get us water which was warm I think they should just leave a jug of ice water in the table like they do at pancake house then u don’t have to chase anyone down as well the appt cajun shrimp should be like jumbos not little pieces for the price snd it’s an spot use bigger shrimp as well we were there for a bday and the free dessert took forever to come out overall was good just alittle slow at times maybe hire a few more people to come around with water or coffee or extra people to help
    More info
    Boston Pizza - KenastonPrice: Moderate• Pizzeria• Southwest Winnipeg
    4.3
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