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All Winnipeg plans

Date Night in Winnipeg — Curated for Two

Rooftop cocktails, low-lit dinners, jazz at 10 — paced like a real night out.

Friday

  1. 8:00 PM

    Deer + Almond

    Global small plates · $$$ · Exchange

    Low-lit dinner — Inventive, dim, the city's tasting-menu darling.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Exchange — short walk from your other stops
    • ·A shoulder-season favorite

Saturday

  1. 11:00 AM

    Clementine

    Brunch · $$ · Exchange

    Slow brunch — Best brunch on the prairies, line by 9.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Exchange — short walk from your other stops
    • ·A shoulder-season favorite
  2. 4:00 PM
    Assiniboine Park
    Outdoors · Tuxedo

    Gardens, the Leaf conservatory, free outdoor theatre.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Tuxedo — short walk from your other stops
    • ·A shoulder-season favorite
  3. 8:00 PM

    Segovia

    Spanish tapas · $$ · Osborne

    Tiny room, sherry, jamón.

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    Why this pick
    • ·Date-night ready — low-lit, cocktail-paced
    • ·Keeps you in Osborne — short walk from your other stops
    • ·A shoulder-season favorite

Want a different vibe?

Try one of the other ready-made Winnipeg plans.

✨ Classic 48 Hours🍽️ Foodie Edition💞 Romantic Weekend🥃 Boys' Night Out💃 Girls' Night Out📸 First-Timer👨‍👩‍👧 With Kids🧭 Solo Edition💸 On a Budget