Isabella Monroe’s Guide to the Perfect Rooftop Experience

If you’re seeking a quiet, yet refined evening to connect with someone special, the rooftop bars in Toronto are the places where intimacy meets luxury. For me, the ideal rooftop experience isn’t just about the view—it’s about the feeling the space gives you. It’s about the way the lights shimmer in your wine glass, or the soft breeze that carries your conversation long after the city’s hustle fades into the background.

Here’s a look at the most intimate rooftop spots where you can have a conversation that feels like it’s meant for two—and nothing else matters.

Lavelle – Where Elegance Meets Sky

16 Stories of Bliss Above King West

Lavelle always has a magnetic pull—it’s not just the unobstructed view of the CN Tower or the infinity pool that tempts you, it’s the exclusivity and effortless elegance. A space where time slows down, and every moment feels like it belongs to just you and your guest.

For a first date or a special occasion, Lavelle sets the stage perfectly. The sound of soft jazz plays in the background as you settle into plush lounge chairs, gazing out at the twinkling skyline. It’s sophisticated but never too stiff, a place where natural conversation flows, helped along by expertly crafted cocktails.

Isabella’s Experience:

“I find Lavelle to be the perfect place for someone who appreciates both luxury and discretion. A place where no one bothers you, and the evening feels drawn out, without being rushed. The cocktail menus here change seasonally, and I can’t resist their signature smoked old-fashioned. A quiet touch of smoke and citrus. Every sip lingers, just like the moment.”

Harriet’s Rooftop at 1 Hotel – Eco-Chic Romance

A Touch of Green Above the City

When I’m in the mood for something more laid-back yet still indulgent, Harriet’s Rooftop is my choice. With its eco-conscious design, natural elements, and breathtaking views of Toronto’s skyline and the CN Tower, it feels like a retreat. The plants and reclaimed wood accents create a soft, calming atmosphere that’s perfect for a conversation that flows effortlessly.

Whether you’re catching the sunset or enjoying an evening drink, Harriet’s always feels like an escape—right in the heart of the city.

Isabella’s Experience:

“Harriet’s has an intimacy that’s hard to find in a bustling city like Toronto. The soft greenery, coupled with the dim lighting and the sound of the wind rustling through the leaves, makes it the perfect place to connect without distractions. One of my most cherished evenings here was with someone who understood the quiet moments. We didn’t need much. Just good conversation and a glass of sauvignon blanc.”

The Roof at SOCO – Where the Skyline Becomes Yours

An Evening Above the Rest

If you’re looking for a place that offers both sophistication and an incredible view, The Roof at SOCO should be on your list. With its panoramic views of the lake and downtown, it’s ideal for watching the sunset while sipping cocktails. I find that SOCO’s ambiance perfectly balances class and comfort, making it ideal for a romantic nightcap or a more casual meet-up.

Whether you’re enjoying an early evening sundowner or a late-night drink, the views will always leave you speechless, and the setting will leave you wanting to linger.

Isabella’s Experience:

“The best thing about SOCO is how unobtrusive it is. The views speak for themselves, and the vibe is quietly luxurious—the perfect backdrop for a private conversation. I’ve often gone there after a dinner at one of Toronto’s chic restaurants to share an intimate drink while the CN Tower lights up behind us. It’s the kind of place where time doesn’t matter.”

Olivia Hart’s Take on Isabella’s Favorite Rooftops:

“Isabella’s taste in rooftops always surprises me—she has an eye for places that blend sophistication with warmth. She finds spots that feel like they belong to the two of you, no one else. It’s not about the crowds, it’s about the intimacy of the space. Whether it’s Lavelle’s heights or Harriet’s serene retreat, she knows exactly where to go for a memorable evening.”