Eric’s Charleston Proposal to Sydney at the Charming Stolls Alley, South of Broad

As a Charleston Proposal Photographer, I have to say—Stolls Alley is one of the most romantic spots in the city. Tucked away South of Broad, this quiet, hidden street is lined with ivy-covered walls and historic brick columns. It’s a total hidden gem and the perfect place for an intimate Charleston proposal.

Eric flew in from Tennessee just hours before the big moment. He teamed up with Jena from Propose Charleston to plan every detail behind the scenes. The goal? To create a magical surprise for Sydney—and wow, did they deliver!

The Proposal Plan: Eric told Sydney they had dinner plans in one of the darling historic neighborhoods. Since it was her first time in Charleston, she was completely along for the ride. Jena and Eric picked Stolls Alley as the proposal location. It’s quiet, private, and just oh-so-Charleston.

Jena styled the sweetest setup in the middle of the alley. Candles, florals, and of course—a bottle of champagne on a beautiful table, waiting for the perfect moment. Meanwhile, Jena and I tucked behind an ivy-covered wall, camera ready.

When Eric and Sydney arrived, her reaction was priceless. She was completely surprised! The moment he dropped to one knee, she lit up. And yes—she said YES!

Afterward, they toasted with champagne and took it all in. Sydney’s marquise engagement ring was absolutely stunning. (Well done, Eric!) We spent some time wandering through downtown Charleston, taking more photos in the golden light. The window boxes were blooming, the streets were glowing—it was a perfect spring evening.

Cheers to Sydney and Eric’s Charleston Proposal at Stolls Alley!

Charleston will always be a part of their love story. And who knows—maybe they’ll choose to get married here too! I’m so excited to share photos from their Charleston proposal at Stolls Alley on the blog today. These moments are always such a joy to capture.

If you’re planning a proposal and looking for a Charleston Proposal Photographer, I’d love to hear your vision and help bring it to life!

Creative Team:
Planning: Propose Charleston
Florals: Propose Charleston
Photography: Jen Keys Photography