How to Propose: Romantic Ideas You’ll Both Love (Plus Local Kelowna Venues + FAQs)

Pickadilly's
Aug 23, 2025
4 min read

Updated: Aug 31, 2025

At Pickadilly’s, we know that planning a proposal is one of the most exciting — and nerve-wracking — moments of your life. You want it to feel magical, effortless, and deeply personal. That’s where we come in.

As Kelowna’s proposal and event styling specialists, we create everything from intimate at-home setups to show-stopping winery experiences. This guide shares our top tips, romantic ideas, and answers to the most common proposal questions we hear — so you can start planning your perfect “yes.”

Romantic candlelit proposal setup in Kelowna with Real Touch flowers, candles, and luxury décor by Pickadilly’s. — Candlelit Proposal

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Romantic Proposal Ideas (At Home, Airbnb & Private Settings)

Some of the most unforgettable proposals happen in private, cozy spaces. Pickadilly’s designs can transform even the simplest setting into something extraordinary.

✨ At-Home Proposals (Styled by Pickadilly’s)

First Date Re-Creation: We’ll style your space to mirror that special first memory — flowers, candles, and custom details included.
Memory Wall: Let us build a floral or photo backdrop highlighting your journey together.
Backyard Glow: Our Real Touch flowers and candles can turn your yard into a dreamy proposal scene.
Movie Night Magic: Imagine watching your favorite film when the screen fades into a personalized “Will You Marry Me?” sign.

🏡 Airbnb Proposals in Kelowna

Kelowna has stunning Airbnb properties with lake views, modern interiors, and cozy fireplaces. We regularly style Airbnbs for couples who want privacy with a luxury feel. With Pickadilly’s, you don’t lift a finger — we arrive before you, set up the candles, florals, and signage, and leave everything ready for the moment you walk in.

Romantic Airbnb proposal in Kelowna styled with candles, Real Touch flowers, and lake views. — Air BnB Proposal

Best Places to Propose in Kelowna & the Okanagan (Styled by Pickadilly’s)

We’ve styled proposals across the Okanagan, from lakefront parks to iconic wineries. These are our most requested venues — and the ones we recommend to couples who want something unforgettable.

Intimate vineyard proposal overlooking Okanagan Lake, styled with candles and roses. — Winery Proposal

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🍷 Wineries & Vineyards

Mission Hill Family Estate – Elegant architecture and sweeping lake views, often paired with a private dinner we can help arrange.
Summerhill Pyramid Winery – Organic, biodynamic, and magical — especially with our signature floral heart as the centerpiece.
Winery – A rooftop reveal styled with candles and florals makes for a jaw-dropping surprise.
Quails’ Gate Winery –

🌿 Outdoor & Scenic Spots

Knox Mountain Lookout – A panoramic view styled with one of Pickadilly’s floral meadow arcs.
Bertram Creek Park – Natural and serene, enhanced with our ground floral designs and candlelit walkways.
Waterfront Boardwalk & Stuart Park – Perfect for a romantic sunset stroll that ends in a styled setup.
Myra Canyon Trestles – A dramatic and adventurous proposal spot we can prepare with portable florals and signage.

Winter Kelowna beach proposal with a candlelit rose garden setup, styled with Real Touch flowers and décor by Pickadilly’s. — Kelowna beach proposal

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✨ See this proposal come to life on TikTok: @pickadillys

❄️ Winter Proposals in Kelowna

Yes, people travel here in winter! Kelowna’s snow-dusted vineyards and cozy wineries create a uniquely intimate atmosphere. Pickadilly’s provides winter-ready setups — think oversized floral hearts glowing against the snow, or a candlelit Airbnb after a day at Big White.

Proposal Timing & Etiquette: FAQs (Answered by Pickadilly’s)

We get these questions all the time when helping couples plan:

💍 What knee do you propose on?

Traditionally, it’s the left knee. But at Pickadilly’s, we always remind clients that comfort (and the photographer’s angle!) matter most — so choose what works for you.

🍽️ Should you propose before or after dinner?

We recommend before dinner so you can relax and enjoy your meal after. Many of our clients propose at sunset, then celebrate with a private dinner we help arrange.

Rooftop proposal followed by dinner at the same venue

⏳ How soon is too soon to propose?

There’s no magic timeline — but we encourage couples to wait until they’ve had the important conversations. When you’re ready, Pickadilly’s will make sure the proposal feels flawless.

🌅 When is the best time of day to propose?

Golden hour (just before sunset) is always our go-to. It’s romantic, cinematic, and gives your photographer perfect light.

Why Choose Pickadilly’s for Your Proposal

Planning a proposal in Kelowna doesn’t have to be stressful. With Pickadilly’s, you get:

Luxury faux florals that look and feel real, styled into custom designs.
Turn-key packages with candles, signage, and décor delivered and set up for you.
Local expertise — we know which wineries, Airbnbs, and parks allow private setups, and we handle the logistics.
Year-round styling — from sunny vineyard proposals to cozy winter getaways.

We create the magic so you can focus on the moment.

Final Thought: Make It Yours

The most romantic proposals are the ones that feel like you. Whether it’s a candlelit Airbnb styled by Pickadilly’s, a snowy winery terrace, or a lakeside sunset with a floral meadow arc — if it reflects your love story, it will be unforgettable.