St. Augustine Proposal Photographer
We hide. You propose. We capture their reaction.
Surprise Proposal Photography in St. Augustine
As your St. Augustine proposal photographer, we know you only get one shot at capturing their face when they realize what's happening—no do-overs, no "let's try that again." We take that responsibility seriously.
We've photographed over 100 surprise proposals in St. Augustine—from nervous partners pacing the Lightner Museum courtyard to beachside sunsets with hidden photographers. We know how to be invisible when it matters and present when the celebrating starts.
After the "yes" (because it's always yes), we step out for a quick celebration session. 15-20 minutes of portraits while you're both glowing, ring on finger, still processing what just happened. These are often our favorite photos.
Recent Sessions
Proposals and engagements we've captured recently
How Surprise Proposal Photography Works
Here's exactly what happens so you can focus on the ring (and the question).
Reach Out
Contact us 2-3 weeks before (or sooner if needed). Share your plan, location ideas, and timing.
Planning Call
We finalize the location, positioning, backup plans, and exactly how the moment will unfold.
Day-Of Setup
We arrive early, get into position, and blend in. You won't see us until after the question.
The Moment
We capture the question, the reaction, the tears, the celebration. Every emotion, documented.
Celebration Portraits
15-20 minutes of couples photos right after. You're engaged—let's capture that glow.
Gallery Delivery
Your images delivered within ~1 week. Faster than our standard turnaround because we know you're excited.
Nights of Lights Proposal Photography
November through January, downtown St. Augustine transforms into a winter wonderland with millions of white lights draped across every building, tree, and lamppost. It's one of the most romantic settings in Florida—and one of our favorite times for proposal photography.
The lights create stunning bokeh in photos, turning ordinary street corners into magical backdrops. We've captured 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.
Nights of Lights proposals require extra planning—crowds are larger and positioning is trickier—but the results are worth it. The colorful light reflections, the festive atmosphere, the cozy winter vibe. Your proposal photos will look like something from a holiday movie.
Pro tip: Weeknight evenings (Tuesday-Thursday) have smaller crowds and easier parking. We'll help you pick the perfect timing.
Best Places to Propose in St. Augustine
Not sure where to pop the question? Here are spots we've used successfully—each offers something different, and we can help you choose based on your partner's style.
Lightner Museum Courtyard
Intimate, elegant, and easy to position a hidden photographer. The Spanish Renaissance architecture provides natural framing with beautiful arches and a central reflecting pool. Our most popular proposal spot—the enclosed courtyard means privacy without sacrificing grandeur.
Plaza de la Constitución
Historic downtown with sunset views of the Cathedral Basilica. Romantic and quintessentially St. Augustine with its gazebo and oak trees. Absolutely stunning during Nights of Lights season when millions of white lights transform the plaza into pure magic.
St. Augustine Beach
Classic sunset proposal on the Atlantic Ocean. We position down the beach with a long lens and capture the moment as you walk toward the water. The sound of waves, golden light, and endless horizon create an unforgettable backdrop.
Castillo de San Marcos
America's oldest masonry fort with panoramic views of the Matanzas Bay and Bridge of Lions. The 17th-century coquina walls create a backdrop that feels significant and timeless—perfect for history lovers and couples who want something truly unique.
Washington Oaks Gardens
Secluded state park with formal gardens and a dramatic coquina rock beach. Perfect for partners who love nature and want privacy away from downtown crowds. The contrast of manicured gardens and rugged Atlantic coastline offers incredible variety.
Magnolia Avenue
St. Augustine's most iconic street—a canopy of ancient live oaks draped in Spanish moss stretching as far as you can see. Timeless Southern charm with dappled light filtering through the trees. Quiet, romantic, and perfect for couples who want that classic Florida magic.
The Bayfront
The seawall walkway along Matanzas Bay with the iconic Bridge of Lions as your backdrop. Sailboats, water views, and that perfect St. Augustine skyline. Golden hour here is spectacular—warm light on the water with the historic bridge framing the moment.
Castillo Green
The grassy lawn facing the Castillo de San Marcos with the fort, towering palm trees, and sparkling bay all in frame behind you. A uniquely St. Augustine scene that captures the city's Spanish colonial heritage in one stunning view.
Private Locations
Vacation rentals, boat charters, helicopter rides, restaurant private rooms—we've done them all. If you have a meaningful spot in mind, we'll make it work. Your spot, your story, your way.
Not sure which location fits? We'll help you pick the perfect spot during our planning call.
What to Expect
Before Your Proposal
Consultation to finalize location and timing. We'll discuss positioning, backup plans, and exactly how the moment will unfold. You'll feel prepared and confident.
Day Of
We arrive early and get into position. You won't see us until after the question. We capture the proposal, the reaction, the tears, and the celebration.
After
We send a selection of highlight images ASAP—usually same day or next morning. Your full gallery with download rights arrives within 1-2 weeks. Optional: book a full engagement session later.
Proposal Photography Pricing
Surprise Proposal Photography: Starting at $650
Includes planning consultation, hidden photographer coverage, and bonus celebration portraits.
Proposal + Engagement Package: Starting at $950
Proposal coverage plus an engagement session at a later date.
Looking for engagement session pricing? See engagement sessions →
What Couples Say
After they said yes
M
"Rob and Jill were absolutely phenomenal. They worked with very short notice and were able to capture my surprise proposal so well. The photos came back very quickly and they looked absolutely amazing. Thank you."
J
"I've worked with Rob on a few projects by this point and wanted to take a minute to write a review for anyone searching for a great photographer. First, let me say that Rob's passion for photography is infectious and gets everyone excited who works with him. Then, when you see the quality of his work, you know you've picked the right photographer. His professionalism and dedication to his craft is awestrucking. Rob's vision and the way that he captures a picture and makes you feel like you are part of the moment is simply beautiful. From professional headshots, to parties, proposals, weddings, maternity photos and all of the things in between, Rob would be the perfect photographer to follow you and capture all of your beautiful moments in life."
Awards & Recognition
After the Proposal: Engagement Sessions
Many couples book a full engagement session a few months after their proposal—different location, more time, a chance to use the photos for save-the-dates and your wedding website.
Since we already know you from your proposal, we'll feel like old friends by then. No awkward "getting to know you" phase.
Learn About Engagement SessionsProposal Photography FAQ
Everything you need to know about planning your surprise
2-3 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! We arrive early, position ourselves discreetly (often pretending to photograph something else), and blend into the scenery. Over 100 successful proposals—we haven't blown anyone's cover yet.
We always discuss backup plans during our planning call. Many indoor locations work beautifully for proposals—Lightner Museum courtyard, restaurant private rooms, even the covered areas of downtown. We'll have options ready.
Yes! After capturing your proposal, we do a bonus 15-20 minute celebration session on the spot. Many couples also book a full engagement session a few months later at a different location.
Planning consultation, hidden photographer coverage of the proposal moment, celebration portraits immediately after. We send highlight images ASAP (usually same day), with your full gallery delivered within 1-2 weeks. Starting at $650.
Absolutely. We've photographed proposals at dozens of locations around St. Augustine and know which spots work best for different times of day, seasons, and styles. We'll help you pick the perfect spot.
Surprise proposal photography starts at $650, which includes planning consultation, hidden coverage of the moment, celebration portraits after, and all edited images. 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.
You'll want to look nice but not suspiciously dressed up—your partner might catch on! We recommend smart casual that fits the location. Solid colors photograph better than busy patterns. Your partner will be wearing whatever they normally would, so the focus is really on the moment, not the outfits.
The hidden portion is typically 15-30 minutes (we arrive early to get positioned). The proposal itself is just a few magical minutes. Afterward, we do a 15-20 minute celebration session for portraits together. Total time from our arrival to wrapping up is usually about an hour.