Dreamy Rosemary Beach Surprise Proposal at Sunset

This session in Rosemary Beach was the absolute sweetest. You can feel the love and excitement between Josh and Grayson in every single photo. The colors, the ocean breeze, the happy tears — literal magic. Their surprise proposal followed up with engagement photos was the dreamiest way to celebrate such a big moment in their story. Keep reading for all the behind-the-scenes goodness and details!

Josh + Grayson’s Rosemary Beach Surprise Proposal

A dreamy spring evening with a lil’ secret

Two of my favorite seasons here in 30A? Spring and fall — and for good reason. Josh and Grayson got engaged in March, right in the middle of our busy spring break season, but honestly? It’s such a perfect time to be here. The weather is warm enough for beach days, still breezy enough to not melt, and we’re not in the thick of hurricane season. Plus, right before sunset, the beach crowds usually head out to get ready for dinner…aka prime proposal time.

Josh reached out in January with plans to propose when both of their families would be visiting for Grayson’s birthday. Rosemary Beach was already such a meaningful place to them — and since Grayson lives here, he knew it would be the perfect spot. His plan? Keep it a total surprise and have me there to capture all the raw emotion when he popped the question. They had dinner reservations at Ambrosia under the cover of birthday celebrations, so starting the night with a “casual” sunset beach walk? Chef’s kiss.

We kept it simple and true to them. Josh and I mapped everything out in advance — exactly where I’d be on the beach, what to look for, and which direction to walk from the access point. I got there a couple hours early (because yes, that’s the kind of Type A energy I bring to surprise proposals 😅), found a clear spot, and texted him the go-ahead. Once I saw him reaching into his pocket, I grabbed my camera and captured the moment.

A Note About Photos at Rosemary Beach: Photography is not allowed within the town or private beaches of Rosemary Beach without a permit. To stay fully legit, we reached out to the Rosemary Beach team ahead of time to secure both a beach pass and photography permit. You can request one here if you’re planning a session!

A proposal straight out of a romance novel

This proposal was the sweetest thing. Everything about how Josh and Grayson love each other — the way they laugh, the way they look at each other, interact — it all came through so beautifully. I'm a total romantic and grew up in the wedding industry, so getting to witness and document moments like this? Never gets old. These moments always make me emotional obviously, lol. 

After they had their moment to soak it all in, we stayed on the beach for a few more photos. Honestly, this is one of the best parts of having a photographer there for your surprise proposal — you're already in the moment, the emotions are fresh, and you get the most natural, effortless, and joy-filled engagement photos right after. 💍

Soft blues, sweet nothings, & a stunning golden hour

Okay, can we talk about their outfits for a sec?! Grayson wore this dreamy floral dress and Josh had a subtle plaid button-up — and they looked SO good against the white sand and ocean blues. I’m always biased toward neutrals, blues, greens, and pastels for beach sessions, especially during golden hour. The mix of soft sky tones with the warm sunset glow? My favorite combo.

When picking outfits, my top tip: choose what makes you feel good. Wear something that feels like you and makes you feel confident. Love neutral tones? Go for it. Obsessed with color? Bring it in. Patterns? Totally allowed — just make sure they complement each other. (Like Grayson’s florals with Josh’s plaid — such a cute combo.)

A post-engagement party with loved ones

If you’re wondering how to include your family after a private proposal moment, take a note from Josh and Grayson. Their families didn’t join us on the beach, but we ended the night with a little celebration at their house. There were champagne toasts, personalized cookies, tons of hugs, and so many happy tears. It was the perfect way to wrap up such a meaningful day — and we got a few sweet family photos in, too.

Rosemary Beach Proposal + Engagement Photographer

Okay but seriously… hiring a photographer for your engagement? Total game changer. Whether you’re planning the ultimate surprise or just want to bottle up all those “we just got engaged!!!” vibes on the beach, this is your sign to do it.

Photos that actually feel like you >>> anything else. Take a cue from Josh and Grayson — their day was fun, intentional, and full of love.

Need help planning the perfect moment? I got you. Fill out this contact form and I’ll send all the info your way!

Check out some other tips here:
📸 Engagement Photo Tips & Inspiration
💍 Caitlin + Royce’s Beach Engagement Photo + Video
🌊 30A Engagement Photos

Already diving into wedding planning? Check out my roundup of favorite 30A wedding venues for inspo!