
Will put his whole heart into planning this 20 South Battery proposal for Olivia. He chose the place where they spent their very first Valentine’s weekend together and reserved the courtyard just for the occasion. Getting to come back to that same place to ask her to marry him? Pretty damn sweet.
There were flowers, rose petals, candles, and so much love behind it all. It was also very, very hot. But we’ll get to that.
One thing I love about 20 South Battery is how much you can do without going far. You have this beautiful courtyard for the proposal, and White Point Garden is right across the street. We can wander under the oak trees, walk along the water, and find little spots for photos along the way.
Charleston already has such a romantic feel to it. The old houses, the gardens, the light coming through the trees. And afterward, you can head downtown for dinner and make a whole date out of it. You’re already dressed up and newly engaged. Might as well soak it all in.



When I arrived, Ashley with Stunning & Brilliant Events was there with some helping hands getting everything ready. Ashley, Olivia, and I all used to work together at The Vendue, so getting to come together again for this felt like such a sweet full-circle moment.
There were flowers, flameless candles, and rose petals throughout the courtyard and ice cold celebratory champagne waiting on them. It all looked so beautiful. Will had put so much heart into planning this for Olivia, and Ashley helped bring it to life.
Then they arrived, Olivia in a beautiful white dress, and Will got down on one knee. Back at the place where they spent their first Valentine’s weekend together, now with a whole new memory to take home.
It was emotional and truly one of those moments I feel lucky to be there for. Getting to photograph something that means this much to someone will never get old.






Afterward, we took photos around the property and enjoyed some celebratory champagne. And when I say it was hot, I mean we absolutely needed a minute to cool off.
We stepped into the lobby for a little air conditioning and took a few photos there, too. The lobby was the only indoor space we used. If you’re dreaming of portraits in the hotel’s other indoor spaces, there’s an additional charge, so make sure to arrange that with the hotel beforehand.
I love having time for portraits after a proposal. You’ve just had this huge moment together, and now you get to let it sink in a little. Take a breath, have some champagne, and enjoy the fact that you’re actually engaged.
Will and Olivia, thank you for letting me capture this piece of your story. What a magical day.











If you’re thinking about proposing here, start by reaching out to the hotel about the space and what you have in mind. Will reserved the courtyard for their proposal, so it’s worth talking through those details before making your plans.
And give yourselves a little time afterward. Take the photos, wander around, go celebrate. You don’t have to fit everything into the few minutes it takes to ask the question.
If you’re looking for a Charleston proposal photographer, tell me what you’re dreaming up. Whether you have every detail figured out or just know you’re ready to ask your person, I’d love to help you capture it.
© tara leigh photography 2025
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