Winery Proposal in Kelowna: Romantic Engagements at The Gallery Winery

Pickadilly's
Aug 4
3 min read

If you’ve been dreaming of a proposal surrounded by breathtaking lake views, rolling vineyards, and world-class wine, a winery proposal in Kelowna might just be your perfect setting. Nestled along the scenic Westside Wine Trail, The Gallery Winery offers an unforgettable blend of romance, elegance, and charm—making it one of the most sought-after places to pop the question in the Okanagan Valley.

Proposal at the Gallery Winery

Why The Gallery Winery is Perfect for Your Proposal

The Gallery Winery is more than just a stunning backdrop—it’s an experience. Overlooking shimmering Okanagan Lake, this hidden gem boasts panoramic views that turn golden at sunset, providing a natural glow that’s ideal for photos.

Known for its award-winning white wines and sparkling vintages, it’s also the perfect spot to toast your new engagement. Imagine clinking glasses of crisp, celebratory bubbles as you soak in the moment and the scenery.

Oversized red floral heart proposal setup at The Gallery Winery in West Kelowna, overlooking Okanagan Lake, with a red rose-lined runway and “Will You Marry Me?” sign. — Luxe Kelowna Winery Proposal

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Optional Add On, Professionally Wrapped Engagement Bouquet

Elevate your proposal with a professionally wrapped red rose bouquet, the ultimate romantic gesture after the “yes.” Each bouquet is styled with care and can be wrapped in luxurious Dior-inspired paper with optional embellishments such as satin ribbons, custom tags, or decorative accents. It’s a beautiful way to surprise your partner and create stunning engagement photos—while giving them a keepsake they’ll cherish forever.

Romantic Proposal set up in Kelowna with red rose bouquet — Romantic Proposal in Kelowna

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Multiple Setup Options to Match Your Style

While the Luxe Heart is a showstopper, it’s not the only way to create magic at The Gallery Winery. We also offer:

Elegant Garden Setups – Perfect for couples who prefer a softer, more romantic vibe. Think pastel florals, greenery accents, and vineyard views in the background.
Signature Pillars – Tall floral pillars framing you both as you say “yes,” designed to match your color palette.
Seasonal Styling – From lush spring blooms to cozy autumn tones, we can design a setup that feels personal and in tune with the season of your proposal.

Whether you envision a grand gesture or an intimate moment, Shannon and her team will create a design that reflects your love story.

Air BnB Proposal set up in Kelowna — Air BnB Proposal in Kelowna

Why Couples Love Winery Proposals in the Okanagan

Romantic Setting – The combination of lake views, vineyards, and golden sunsets is unmatched.
Celebratory Vibes – Pop a bottle of the winery’s own sparkling wine right after the big moment.
Picture-Perfect Backdrops – Ideal for engagement photos you’ll cherish forever.

Pickadilly’s Proposals: Crafted by an Award-Winning Stylist

When it comes to proposals, every detail matters. That’s why so many couples turn to Shannon with Pickadilly’s Proposals. As a recipient of Kelowna’s Top 40 Over 40, Shannon brings proven expertise, a designer’s eye, and a personal touch to every event. Her goal? To make your proposal seamless, stress-free, and absolutely unforgettable.

One of our most loved designs for The Gallery Winery is our Signature Luxe Heart—an oversized floral heart overflowing with red roses, paired with a red runway lined with hundreds of roses rose petals and roses swaying in the breeze. Add a “Will You Marry Me?” sign and you have a breathtaking, cinematic moment worthy of the “yes” you’ve been waiting for.

Shannon Johnston top 40 over 40 Kelowna - proposal planner

Ready to Start Planning Your Winery Proposal?

If you’re ready to plan your Kelowna winery proposal, contact Shannon with Pickadilly’s Proposals. With award-winning styling expertise and years of experience making proposals flawless, Shannon will bring your dream moment to life.

📍 Located on the Westside Wine Trail in West Kelowna, The Gallery Winery is a true Okanagan treasure. Let’s make your proposal here the beginning of a lifetime of beautiful memories.