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Published Apr 05, 2025 • Last updated Apr 05, 2025 • 5 minute read
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Alena Rustic Italian, tucked along Roblin Boulevard in Charleswood, brings authentic Italian cuisine to Winnipeg. Photo by Handout /Winnipeg SunArticle content
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When you walk into Alena Rustic Italian, the smell alone is enough to stop you in your tracks. That unmistakable scent of wood-fired cooking, warm bread, and bubbling cheese — if comfort had a smell, this would be it. It’s the kind of place where pizzas arrive with perfectly blistered crusts, pastas come out steaming in rich sauces, and every dish is thoughtfully made. On the wall, the words Mangia bene, “eat well,” set the tone for what’s to come.
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Tucked into a strip along Roblin Boulevard in Charleswood, Alena isn’t trying to be flashy. It doesn’t need to be. It’s the kind of restaurant you come back to again and again — not just for the food, but for how it makes you feel while you’re there. With the inviting smiles of the staff and the cozy yet vibrant atmosphere, it’s no wonder Alena Rustic Italian has become a cornerstone of the community.
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I had the pleasure of chatting with Doug Stephen, President of WOW! Hospitality, and Alena’s Executive Chef and Partner, Michael Dacquisto — two familiar faces who’ve helped shape Winnipeg’s dining scene.
Alena is part of the WOW! Hospitality family of restaurants, known for creating some of the city’s most memorable dining experiences. Michael has been with WOW! Hospitality for 30 years, playing a key role in researching and opening many of its restaurants, including 529 Wellington and Prairie’s Edge. Together, they’ve created something truly special at Alena.
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“We wanted it to feel like a neighbourhood spot,” Doug explained. “The kind of place you could go to every week — whether it’s a quiet dinner with your partner or a big family get-together. And just as importantly, the food had to be exceptional.”
Chef Dacquisto brings a deep love for Italian cooking, and it shows. “Italian food is honest,” he shared with me. “You’re not hiding behind anything. It’s simple ingredients, done right. That’s what I love about it.”
Let’s talk about the food, because that’s really what Alena is all about. The garlic butter knots are a must to start. Soft, golden, garlicky little clouds served with a San Marzano tomato sauce so good, you’ll want to drink it.
The calamari? Easily the best in the city. Perfectly crisp and light — not overly battered or greasy — just the way it should be. Served with roasted lemon and the most delicious aioli for dipping.
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Alena’s wood-fired pizzas will have you wanting more. Photo by Handout /Winnipeg Sun
The wood-fired pizzas? Perfection. My go-to is the chicken pizza with garlic cream sauce, caramelized onions, wood-fired chicken, and arugula — all on a crisp, golden crust with just the right amount of char. Trust me, it’s one you need to try. If you love a pasta that’s rich without feeling heavy, go for the carbonara — creamy with a generous shaving of pecorino cheese.
Alena serves some of the best, mouthwatering wood-fired pizza and pasta in the city, alongside an impressive selection of meats, from rotisserie chicken to wild boar chops and grilled steaks. And their wine list? Just as thoughtfully curated — approachable, well-balanced, with a selection that pairs beautifully with the menu. Whether you’re in the mood for a bold Italian red or something crisp and refreshing, there’s something for every palate.
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If you’re looking to try something a little more special, ask about Michael’s Cellar — a selection of premium bottles handpicked by Chef Dacquisto himself. It’s one of those behind-the-scenes touches that shows just how much care goes into every part of the experience.
The food is incredible across the entire menu, but you’ll want to save room for dessert. The zeppole are a must — warm, fluffy doughnuts dusted in cinnamon sugar, served with a rich chocolate dipping sauce. My husband and I shared them, but in my dreams I would have finished the plate myself.
We also tried the classic tiramisu — light, creamy, and everything you want it to be. And the affogato, with vanilla gelato and a shot of hot espresso poured over top, was simple, bold, and the perfect way to end the night.
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Alena’s open kitchen adds to the inviting ambience and charm. Photo by Handout /Winnipeg Sun
The atmosphere at Alena is cozy, relaxed, and full of charm. It’s the kind of space where you can settle in and stay awhile — whether you’re on a date night, out with friends, or gathering the family for a special dinner. The open kitchen adds to the experience. Throughout your meal, you can watch the chefs at work, sending beautifully plated dishes in and out of the wood-fired oven. It brings a sense of connection to the food, and a little theatre to the table.
“We wanted Alena to be the kind of restaurant where you can enjoy incredible food in a warm, approachable space,” Doug shared. “You don’t have to dress up, but you’ll still feel like you’re out somewhere special.”
It’s not just the food and space that make Alena feel special — it’s the people. The team makes you feel like family. They know regulars by name, they remember your favourites, and they go out of their way to make every guest feel welcome. As I watched the team interact with other tables throughout the night, it was clear this is more than just a restaurant — it’s a place where genuine connection is part of the experience.
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While it’s only been open since 2020, Alena has already carved out a loyal following. Named one of Ciao! Magazine’s Best New Restaurants in its debut year, it’s clear that this isn’t just another Italian spot — it’s one that’s here to stay.
Chef Dacquisto summed it up best: “At the end of the day, it’s about bringing people together. That’s what food is supposed to do.”
Alena Rustic Italian has become a cornerstone of the community with its rustic charm and mouthwatering dishes. Photo by Handout /Winnipeg Sun
Whether you’re popping in for a pizza and a glass of wine or planning a full night out, Alena Rustic Italian is the kind of place that keeps you coming back. It’s the kind of neighbourhood spot that makes you feel like a regular, even on your first visit.
Visit alenakitchen.com to explore the menu and book your table, or call 204-944-8748. Just don’t be surprised if you find yourself planning your next visit before dessert even hits the table.
Alena Rustic Italian is located at 3670 Roblin Boulevard.
— Cassandra Morris, food blogger and recipe developer at cookingwithcassandra.com, and a guest writer for the Winnipeg Sun. She shares the best recipes, essential kitchen tips, and spotlights locally owned restaurants and specialty food must-tries.
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