Proposal Photography · St. Augustine
St. Augustine Proposal Photographer
Rob & Jill | Hidden proposal photographers in St. Augustine since 2014.
Hi, we're Rob & Jill
We're Rob and Jill — a husband-and-wife team who've been photographing proposals around St. Augustine since 2014. We're parents and St. Augustine locals, and after more than a decade we still chase this city's light: the way it pours through the oak canopies and glows off the old coquina walls.
Our approach is easygoing and documentary. Rob sees light and angles like the engineer he used to be; Jill reads the room and knows just when you need a quiet minute. We're there to capture your day the way it actually feels — the belly laughs, the happy tears, the small in-between moments — not to stage it.
More about us →Proposal Photography Portfolio
Museum courtyards, beach sunsets, sandbar picnics — every proposal is different. Tap any couple to see some more images from their gallery.
St. Augustine Proposal Photographer Pricing
Everything included, no surprises
Both of us come to every proposal — hidden, and ready the second you drop to one knee — so you get the surprise reaction in a photo, not just in your memory.
Surprise Proposal
- 80–120 edited images
- Planning consultation with a hand-drawn map of the spot
- Two photographers, two angles — one wide, one tight
- Celebration portraits (15-20 min) right after
- Sneak peek within 24 hours, full gallery within a week
- Online gallery with download rights
Proposal + Engagement
- 80–120 edited images
- Everything in Surprise Proposal
- Full engagement session at a later date
- Different location for variety
- Save-the-date ready images
- Bundle savings vs. booking separately
The courtyard is City property and needs a permit for a proposal. We pull the City permit for a small fee, and the insurance the City requires is covered under our liability policy, so there's nothing for you to arrange.
Nights of Lights Proposal Photography
November through January, downtown St. Augustine is draped in millions of white lights — every building, tree, and lamppost. The lights turn into soft bokeh behind you, and an ordinary street corner becomes the backdrop. We've photographed proposals at Flagler College with the tower glowing behind, at the Plaza surrounded by illuminated palms, and along St. George Street where every storefront sparkles.
Crowds are bigger and positioning is trickier in season, so we plan it tighter — and it's worth it. Pro tip: weeknight evenings (Tuesday-Thursday) mean smaller crowds and easier parking. Year-round, a styled picnic setup or a Valentine's sunset works just as well; we can help with petals, styling, and choosing the spot.
Best Places to Propose in St. Augustine
Spots we know and loveWe scout the spot ahead of time. Ask us which of these fits your plan — we know the sightlines and the hiding spots downtown: the museum courtyard for privacy with grandeur, the Plaza for sunset and the Cathedral, the beach for a long-lens sunset, the Castillo for bay views, Washington Oaks when you want seclusion, and Magnolia Avenue for the live-oak canopy.See all 12 proposal spots in our full guide →
Other Couples Photography Services
Engagement Sessions
Wedding Photography
Elopement Photography
How Surprise Proposal Photography Works
1.Reach Out
Contact us 2-3 weeks before (or sooner if needed). Share your plan, location ideas, and timing.
2.Planning Call
We finalize the location, backup plans, and timing, then hand-draw a map showing exactly where we'll be hiding and where you need to walk.
3.Day-Of Setup
We arrive early, set up flower petals if you want them, and get into position. You won't see us until after the question.
4.The Moment
Both of us shoot it — you get the proposal and the reaction in the same instant.
5.Celebrate
Couples photos right after. You're engaged — let's capture that glow.
6.Delivery
Photos to share before the excitement wears off, and the full edited gallery close behind.
Proposal Photography FAQ
Everything you need to know about planning your surprise
Ask us anything2-3 weeks is ideal for proposal photography. This gives us time to scout the location and plan positioning. That said, we've pulled off proposals with less than a week's notice—reach out even if your timeline is tight.
Not if we do our job right! Both of us arrive early and position ourselves in separate spots so the moment is covered from more than one side. We blend into the scenery, often pretending to photograph something else. We've never blown anyone's cover yet.
Yes! Right after the question we shoot a short bonus session on the spot. Many couples also book a full engagement session a few months later at a different location.
Hidden coverage of the moment, portraits right after, flower petals if you want them, and all of your edited images in an online gallery. Both packages are itemized in the pricing section above.
Absolutely. We know which spots work best for different times of day, seasons, and styles. Check out our guide to the 12 best proposal spots in St. Augustine, or we'll help you pick the perfect spot during our planning call.
Yes. The exterior courtyard is managed by the City of St. Augustine, which charges $250 for a one-hour permit and requires a $1,000,000 liability certificate. We pull the permit for a small fee, and our policy covers the insurance, so you don't deal with either. One timing note: on Fridays and Saturdays the City doesn't issue photography permits after 3:30 p.m., so a weekend courtyard proposal is a morning or early-afternoon plan. Details are in our Lightner courtyard guide.
Surprise proposal photography starts at $650. Pricing varies based on location complexity and timing—Nights of Lights proposals and remote locations may have additional fees. Contact us for a custom quote.