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Valentine’s Day tends to put a lot of pressure on plans – where to go, who to bring, and whether the night needs a touch of romance, feels more social or somewhere in between. Some people spend the day chasing candlelight and dinner menus, while others would rather be laughing with friends or dancing way past midnight. The Drake Hotel has long been a place where those worlds overlap.
This February, the popular Toronto destination is leaning into what it knows best with a lineup of experiences that offers a little bit of everything for everyone.
Valentine’s Day experiences at The Drake
Galentine’s specials
Receive a personalized poem typed on the spot at The Drake! Head to the Classic Wing Lobby for your very own customized poem from Everyday People Typewriter Poems. It’s typed on a vintage typewriter and then tucked into an envelope to keep forever.
When: Feb. 13, 2026
Time: 6 to 9 p.m.
The Dinner with a Side of Sounds series brings live music and elevated dining together in the Drake Lounge. This is your chance to enjoy a romantic prix fixe menu paired with seasonal cocktails. Experience the excitement where live piano blends classic and contemporary hits.
When: Feb. 13, 2026
Time: 7 to 10 p.m.
Later in the evening, head to The Drake Underground for Red Flags Only. This classic Drake-led DJ Dance Party encourages you to “celebrate the bold, messy, unapologetic energy of love. The only rule? Embrace the red flags.”
At least for one night.
When: Feb. 13, 2026
Time: 11 p.m. to late
Valentine’s specials
Put your love story into words with a personalized poem typed on the spot at The Drake. In the Classic Wing Lobby, guests can enjoy a customized poem from Everyday People Typewriter Poems, typed on a vintage typewriter and then tucked into an envelope to keep forever.
When: Feb. 14, 2026
Time: 6 to 9 p.m.
Take Dinner with a Side of Sounds and turn it up a notch. Romance will fill the air as live music and elevated dining blend together for one harmonious evening. Indulge in a romantic prix fixe menu paired with seasonal cocktails.
When: Feb. 14, 2026
Time: 7 to 10 p.m.
Ditch the romance for some laughs! Yalla Comedy presents “Yalla At Me!” right at the Drake Underground. It’s a hilarious live dating experience that’s part comedy show and part interactive dating game, according to organizers.
When: Feb. 14, 2026
Time: 8 to 10 p.m.
Experience a journey through soulful blends, neo-soul, and jazz-funk inspired by album art courtesy of Bia’s Thank You for Listening. Then get your groove on at Love U 4 Ever in the Drake Underground, a Valentine’s dance party spinning disco and house beats late into the early hours.
When: Feb. 14, 2026
Time: 10:30 p.m. to late
Happy Valentine’s Day, Toronto.
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