1
Greek•Downtown•value
Olympia Diner
Olympia Diner has been anchoring Greek home cooking on Portage Avenue in Winnipeg's Westwood/St.
Greek dinnerdinnergroup dinner
Read restaurant page
9.9/10
TastyPals Score
9.0 Google
9.0
1,089 Google reviews
GuideUpdated July 15, 2026
3 Best Places for Calamari in Winnipeg
Where to find the best calamari in Winnipeg — each restaurant rated 4.0★ or higher. Top-rated at 9.0★. Spanning greek and italian kitchens. Curated by TastyPals.
The best places for calamari in Winnipeg are Olympia Diner, Nicolino's, Cibo Waterfront Cafe. Start with Olympia Diner if you want the strongest overall first pick.
Google
Top picks at a glance
Who this guide is for
This guide covers the highest-rated spots for calamari in Winnipeg. Whether you're a local hunting your next regular or visiting and want to eat well, these picks are sorted by quality and review depth.
Quick picks
Olympia Diner
Greek • Downtown
Olympia Diner has been anchoring Greek home cooking on Portage Avenue in Winnipeg's Westwood/St.
Nicolino's
Italian • South Winnipeg
Thirty-three years on Pembina Highway is the kind of tenure that doesn't happen by accident.
Cibo Waterfront Cafe
Contemporary • Winnipeg
Cibo Waterfront Cafe occupies a genuinely unusual building — a repurposed Pump and Screen House on the bank of the Red River that once cooled Downtown Winnipeg's steam heating plant.
Editorial details
On this page
How the restaurants compare
Olympia Diner
Downtown • Greek
9.9/10
TastyPals Score
Price
value
Best for
Greek dinner
Mood
Downtown
Google
Nicolino's
South Winnipeg • Italian
9.9/10
TastyPals Score
Price
value
Best for
Family dinner
Mood
South Winnipeg
Google
Cibo Waterfront Cafe
Winnipeg • Contemporary
9.9/10
TastyPals Score
Price
$$
Best for
patio
Mood
Easygoing
How we chose
We looked for restaurants that feel like a strong fit for the guide topic, not just the most obvious names in the city. The shortlist favors rooms with clear mood, dependable pacing, and enough distinction to help someone decide faster. Read our full methodology →
Room tone
Lighting, pace, and general energy all need to support the reason someone clicked this guide.
Food fit
We favored restaurants that feel best suited for the moment, not just restaurants with broad reputation.
Useful range
The final list tries to give readers enough variation in neighborhood, price, and style to compare real options.
3 ranked picks
Olympia Diner — Olympia Diner has been anchoring Greek home cooking on Portage Avenue in Winnipeg's Westwood/St. James neighbourhood since the Spiridakos family took over in summer 2000 — a lineage worth noting because this is not a concept restaurant or a reinvention of souvlaki for Instagram. The Grecian blue décor (recently refreshed into something more open and airy, though still unmistakably Greek) and the Tuesday-through-Sunday hours signal what this place is actually about: a family-run room where the regulars know what they're getting and come back for exactly that. The price point is as accessible as it gets, which matters in a city where Greek food this earnest can feel underrepresented downtown.
Three dishes have broken through the noise of diner-consensus the way only sustained repetition can explain. The calamari draws the most superlatives — reviewers across multiple platforms describe it as the best they've encountered in Winnipeg, full stop. The lamb souvlaki is the kind of thing that defines a menu: skewered, grilled, and rooted in a preparation that Greek households would recognize rather than question. But the dish that seems to generate the most genuine loyalty is the lemon roasted potatoes — a side that in lesser kitchens gets treated as an afterthought, but here diners specifically single out as exceptional and consistent. That specificity of praise for a supporting dish tells you something real about where the kitchen's priorities are.
Olympia runs Tuesday to Sunday, 11:30am to 9pm, and it's closed Mondays — worth confirming before you make the trip out to 3253 Portage Ave. For groups, the renovated room should accommodate without drama, but for a weekend dinner, calling ahead is the practical move. Order the calamari first, get the lamb souvlaki, and do not skip the lemon potatoes. View restaurant →
Nicolino's — Thirty-three years on Pembina Highway is the kind of tenure that doesn't happen by accident. Nicolino's is the south Winnipeg anchor that a certain kind of diner — the one who wants house-made pasta and a proper room without crossing the Assiniboine — has been quietly counting on since Nick Zifarelli brought his Muro Lucano, Italy-rooted recipes to the 'burbs. The concept sits squarely in the contemporary Italian lane: a kitchen that leans on in-house technique, a dining room with statement lighting that reads more polished than its strip-mall address suggests, and a lounge-plus-patio setup that actually earns the word "neighbourhood" rather than just wearing it. This is not a downtown-tourism play; it's a regular's restaurant that has survived long enough to become a local institution on its own terms.
The kitchen makes its pasta in-house — that's the foundational commitment here, and it shapes what's worth ordering. The chili cream and prawns pasta is described across multiple sources as the restaurant's most popular pasta dish, which tells you something about the house style: flavour-forward, not austere, Italian technique inflected with a willingness to push richness. The famous house breadsticks — made fresh, served six to an order — are the kind of detail that signals a kitchen that cares about the whole table, not just the entrée. The Chèvre Salad has surfaced in recent social posts as a current menu point of pride, and the calamari draws consistent praise in diner reviews as a standout appetizer. The through-line is a kitchen working from tradition while staying loose enough to keep a multi-decade menu feeling current.
The move here is straightforward: start with the breadsticks and calamari, commit to the chili cream and prawns pasta as your main, and if you're coming on a night with live music, book ahead — the combination of patio, lounge, and a room that fills up reliably means you don't want to show up and wing it. Reservations via OpenTable are available; use them. View restaurant →
2
Google
Italian•South Winnipeg•value
Nicolino's
Thirty-three years on Pembina Highway is the kind of tenure that doesn't happen by accident.
Family dinnerfamily dinnertakeout
Read restaurant page
9.9/10
TastyPals Score
8.8 Google
8.8
1,153 Google reviews
Cibo Waterfront Cafe — Cibo Waterfront Cafe occupies a genuinely unusual building — a repurposed Pump and Screen House on the bank of the Red River that once cooled Downtown Winnipeg's steam heating plant. The upper level cantilevers directly over the water, and that industrial provenance combined with river light gives the room an atmosphere most purpose-built restaurants in this city can't approximate. If you're going, the received wisdom is consistent: request the upper level, and time your arrival before peak service to catch the evening light off the Red. These are the kinds of practical details that tend to get passed around a local following, and Cibo has clearly built one.
The menu positions itself somewhere between Mediterranean and eclectic contemporary, anchored by a scratch kitchen that reportedly hand-stretches its own pizza dough. The shareable starters are where the room's reputation concentrates. The Pickerel Fritto and Calamari represent the crowd-facing, audience-aware side of the menu — familiar formats that regulars apparently return to reliably. The Grilled Octopus and Vegetarian Nduja Mussels are the dishes that signal the kitchen's range beyond crowd-pleasers; the nduja preparation in particular is worth noting given that vegetarian versions of that intensely flavored Calabrian staple require genuine technique to carry conviction. Diners who engage with the full menu tend to cite these dishes as representative of what distinguishes Cibo from comparable mid-range rooms.
At a mid-range price point, the value case here is largely built on setting and kitchen sincerity rather than novelty. The Pickerel Fritto and Grilled Octopus are the two dishes that surface most consistently in what regulars recommend to first-timers — a reasonable place to anchor an order while the river does its atmospheric work. View restaurant →
3
Google
Contemporary•Winnipeg•$$
Cibo Waterfront Cafe
Cibo Waterfront Cafe occupies a genuinely unusual building — a repurposed Pump and Screen House on the bank of the Red River that once cooled Downtown Winnipeg's steam heating plant.
patiooutdoorsummer
Read restaurant page
9.9/10
TastyPals Score
8.6 Google
8.6
1,704 Google reviews
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Save these spots to your Winnipeg list in the TastyPals app, then explore similar restaurants when you want a tighter shortlist for the night.
Personalized city picksCleaner shortlistsBuilt for iPhone and Android
TastyPalsTonight
Your taste. Our picks.
Smarter follow-through after the guide: better restaurant context, quicker narrowing, less second-guessing.
For tonight
Date night spots with warm rooms and polished service
Next step
Keep exploring in the app when you want a tighter shortlist