How to Plan the Perfect Surprise Proposal in St. Augustine

Your guide to popping the question in the most romantic city in Florida (with gorgeous photos to match!)

If you’re dreaming about asking the biggest question of your life in the charming streets of St. Augustine, you’re in the right place!! As a photographer who’s captured countless proposals here, I’ve seen it all: the nerves, the excitement, the happy tears... and yes, the unexpected passerby with a pirate hat (hey, it’s St. Augustine!).

So let’s talk about how to plan the perfect surprise proposal in this magical city and get photos you’ll treasure forever!

1. Pick the Perfect Spot (I’ve Got Ideas!)

St. Augustine is packed with stunning backdrops—from cobblestone streets and historic forts to secret garden nooks and golden beaches.

Here are some tried-and-true locations that are proposal perfection:

• Castillo de San Marcos at golden hour

• The Lightner Museum courtyard (so romantic and tucked away)

• Aviles Street – charming and full of old-world flair

• Vilano Beach – peaceful and perfect for sunset proposals

• A private sailboat in the bay (yes, people do this—and it’s incredible)

Not sure where to go? I help all my proposal clients choose a spot that fits their vibe, whether that’s historic, beachy, private, or adventurous!

2. Timing is Everything

Want dreamy lighting and fewer crowds? Go for sunrise or golden hour.

Want your partner dressed up and photo-ready without giving away the surprise? I’ve got sneaky strategies for that (more on that below!)

I always recommend choosing a time that feels natural—maybe before dinner, during a walk, going to watch the sunrise, or as part of a “photoshoot” your partner thinks is for something else!

3. Make a Plan

Here’s where I come in as your St. Augustine proposal photographer and behind-the-scenes co-conspirator. We’ll go over:

• The exact spot & direction you’ll face

• Cues for when to drop to one knee

• Where I’ll be hiding (or how we’ll play it cool if it’s a “posed” session first)

• What to do after the proposal—photos, champagne, calls to family, etc.

You don’t have to figure it all out on your own. I’ve done this many times and can help walk you through every step, right down to where to hide the ring!

4. Make it Personal

This is your moment, and adding personal touches makes it extra special. Some ideas:

• Bring along a love letter to read before or after the big question

• Include your pet or family members if it feels right

• Plan a romantic dinner or surprise celebration after

5. Don’t Forget the Photos!

You’ll never relive this moment in quite the same way again—but the photos? They’ll bring you right back to it! I focus on capturing:

• The nerves (those deep breaths!)

• The exact second of the question

• The reactions—laughs, tears, hugs, ALL of it

• Sweet portraits afterward with the St. Augustine magic around you

And don’t worry—I know how to stay hidden or play it cool until just the right moment!

Bonus: How to Keep the Proposal a Surprise

Let’s be real: some people are hard to surprise! Here are a few tricks that work:

• Say you booked a “couple’s photo session” while visiting St. Augustine (I’ll play along!)

• Enlist a friend or family member to help set the scene

• Schedule it during a walk, while you're exploring, a tour, or right before dinner

• Keep your cool and try not to act too suspicious

Ready to Plan Your Proposal in St. Augustine?

I’m here to help make it easy, stress-free, and magical—with photos that feel like you. Whether you’re from out of town or live locally, I’ll help you plan every detail and capture every second of your big “YES!” moment!

Let’s talk about your surprise proposal! 

Contact Me Here

(I’ll bring the camera—you bring the ring!)