How to Plan a Surprise Proposal in St Augustine With Lee Photo + Video

Start With the Two of You

Before anything else, picture your partner in the moment. The "perfect" proposal isn't about grand or small — it's about what feels like them.

• Private or public? Would they melt at a quiet, just-the-two-of-you moment, or light up with a crowd cheering?
• A meaningful place? Somewhere you had a first date, a favorite trip, an inside joke — that always beats "impressive but random."
• Anyone else there? Some people want family hiding nearby; others want it to be only theirs (more on that below).

The Ring

If you're proposing with a ring, the trickiest part is usually the size. A few discreet ways to figure it out:

• Borrow one they already wear and measure it against a sizing guide.
• Enlist a trusted friend or family member who can ask casually.
• When in doubt, pick a setting that's easy to resize and adjust it later, together.

Don't let ring stress steal the joy — a slightly-off size is a five-minute fix at any jeweler.

Choose Your Spot

Proposing is a little like real estate: location, location, location. You'll both remember exactly where you were standing for the rest of your lives, so it's worth a little thought.

If you don't know St. Augustine, don't sweat it — we've pulled together our favorite spots further down this page, from hushed waterfront chapels to grand courtyards. Tell us your vibe and we'll help you match it to the right corner of the city.

Choose Your Time

This is where a little local know-how really pays off. In St. Augustine, morning is almost always the answer — and here's why.

Waterfront spots — the Mission grounds, the Fort, Vilano Beach — are especially magic at sunrise, when the light comes up over the water right behind you for that warm, glowy look.

Decide What to Say

You don't need a perfect speech. They'll remember the feeling, not the exact words. Still, it helps not to be fumbling in the moment, so jot down a few notes.

• Speak from the heart — start with a memory, then let it lead where it's going.
• Nervous? A short written note or letter can carry the moment beautifully.
• Don't over-script it. Leave room to just be present.

Have It Photographed (Here's How I Fit In)

You're putting all this thought in — it's worth capturing. As your photographer, I do far more than show up with a camera: I help plan the logistics, position myself to catch the real reaction, and stay invisible until the big moment. When couples reach out to me, the first thing I ask is how they want me to fit into the day. There are two ways to play it:

• The "couples session" cover story. I'm introduced ahead of time as a photographer you booked for fun couple photos. It's the low-stress option, great for wide-open spots, and easy to disguise — I can prompt your partner to turn one way while you drop to one knee. The catch: if they're already a little suspicious, a surprise photo session can tip them off.
• Fully hidden. I stay completely out of sight until after you've asked. The surprise stays airtight and the reaction is 100% genuine. This one takes a bit more coordination — we'll map out exactly where you'll each be standing so I can catch their face from the right angle while staying tucked away.

Either way, we plan the details together first: where exactly you want to pop the question, and how you'd like the moment cued. I usually give a subtle signal and wait for your thumbs-up before it all unfolds, and for trickier spots we can even scout the location together beforehand so nothing's left to chance.

Then they say yes — and the celebrating begins. We can roll right into a mini engagement session while you're both still glowing. A few fun things to bring along: champagne to pop (grab two, in case the first one's a flop), sparklers, or a little picnic to land the whole thing.

Want it filmed too? Video can be added as a second storyteller for the moment.

Logistics & Backup Plan

Don't let little details derail the big moment. A few things to lock down:

• Anchor it to an activity. "We have a photo session at 9" works far better than "let's go stand in that park right now."
• Check access. A few spots (private campuses, working churches, sacred grounds) have hours or rules — we'll help you confirm before you plan around them.
• Have a weather Plan B you're equally excited about, or keep the next morning open to reschedule.
• Coordinate outfits without tipping them off — instead of "dress nice," just tell them what you're wearing.
• Hydrate and breathe. Passing out is not part of the plan. You've got this.