This page is still being worked on. Some content may be missing or incomplete. Questions? Reach out to rob@robfutrell.com

Proposal & Engagement Photography in St. Augustine

From the surprise question to relaxed couples portraits—we capture it all.

From "Will You?" to "We Do"

As your St. Augustine proposal photographer and engagement session specialists, we're here to document this chapter of your journey—whether you're planning a surprise proposal or celebrating your engagement with a relaxed couples session.

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.

Many couples book both: we capture the proposal, do a quick celebration session right after, then return months later for a full engagement shoot. Same photographers who know your story, your dynamic, your comfort level. By your wedding day, we'll feel like old friends.

100+ Proposals
15 Years
5★ Rating
275+ Reviews

St. Augustine Proposal Photographer

A surprise proposal only happens once. No do-overs, no "let's try that again." You get one shot at capturing their face when they realize what's happening—and we take that responsibility seriously.

We position ourselves before you arrive, camera ready, blending into the scenery. Sometimes we're tourists taking photos of architecture. Sometimes we're casually sitting on a bench. Your partner won't suspect a thing until you're down on one knee.

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.

Locations we love for proposals: Lightner Museum courtyard, Plaza de la Constitución at sunset, St. Augustine Beach, the Castillo, private restaurant rooms, rooftop terraces, boat charters.

Surprise proposal moment in St Augustine

How a Surprise Proposal Works

Here's exactly how this works so you can focus on the ring (and the question).

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, positioning, backup plans, and exactly how the moment will unfold.

3

Day-Of Setup

We arrive early, get into position, and blend in. You won't see us until after the question.

4

The Moment

We capture the question, the reaction, the tears, the celebration. Every emotion, documented.

5

Celebration Portraits

15-20 minutes of couples photos right after. You're engaged—let's capture that glow.

6

Gallery Delivery

Your images delivered within ~1 week. Faster than our standard turnaround because we know you're excited.

Popular Proposal Locations

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 architecture provides natural framing.

Plaza de la Constitución

Historic downtown with sunset views of the Cathedral. Romantic and quintessentially St. Augustine.

St. Augustine Beach

Classic sunset proposal. We position down the beach and capture the moment as you walk toward the water.

Castillo de San Marcos

Historic fort with stunning views of the bay. Unique backdrop that feels significant.

Washington Oaks Gardens

Secluded garden setting with coquina rock beach. Perfect for partners who love nature.

Private Locations

Vacation rentals, boat charters, restaurant private rooms—we've done them all. Your spot, your way.

Not sure which location fits? We'll help you pick the perfect spot during our planning call.

Engagement Sessions

Engagement sessions are different from proposals—no hiding, no surprises, just you two being yourselves while we capture it. Think of it as a practice run for wedding day photos, except with way less pressure and way more sunset light.

Most couples book engagement sessions 6-9 months before their wedding. The photos end up everywhere: save-the-dates, wedding website, guest sign-in book, wall art. They're also a chance to get comfortable with us before the big day.

Our style? Natural, lifestyle, fun. We'll guide you through poses and movements, but the goal is capturing how you actually are together—the inside jokes, the way you lean into each other, the real stuff.

Sessions typically run 30-90 minutes at one or two locations. You'll receive your gallery within about two weeks.

Engagement session couple in St Augustine

When to Book Your Engagement Session

Ideal timing: 6-9 months before your wedding. This allows time to use photos for save-the-dates and get them printed for your reception.

Season considerations: Spring and fall offer the best light and comfortable temperatures. November through January brings the Nights of Lights—magical for downtown sessions with millions of white lights as your backdrop.

Engagement sessions can be bundled with wedding photography packages or booked separately. Either way, you'll walk into your wedding day already comfortable with your photographers.

St. Augustine Engagement Photo Locations

We'll recommend locations based on your style, the time of year, and the vibe you're going for. Here are some favorites:

Downtown Historic District

St. George Street, Flagler College, Lightner Museum, the Plaza, Spanish colonial architecture at every turn.

Beach Locations

St. Augustine Beach, Vilano Beach, Anastasia State Park. Golden hour on the sand never disappoints.

Parks & Gardens

Washington Oaks Gardens State Park, Treaty Oak Park, Fountain of Youth. Nature lovers, this is your territory.

Unique Options

Nights of Lights (Nov-Jan), sunrise beach sessions, rooftop locations, or somewhere meaningful to your story.

From Proposal to Engagement Session

Many couples book both services with us. The journey looks like this: we capture your surprise proposal, do celebration portraits that day, then return a few months later for a full engagement session at a completely different location.

The advantage? By the time your wedding arrives, we already know you. We know what makes you laugh, how you stand together naturally, which side you prefer to be photographed from. No awkward "getting to know you" phase on your wedding day.

We offer package pricing for couples booking multiple services. Ask us about combo packages.

What to Expect

Before Your Session

Consultation to finalize location and timing. For proposals: detailed positioning plan. For engagements: outfit guidance and location recommendations.

During

Guided direction with natural results. We'll coach you through poses and movements, but the goal is capturing genuine moments, not stiff portraits.

After

Online gallery with download rights. Proposals: ~1 week delivery. Engagements: ~2 weeks. Print ordering available through your gallery.

Investment

Surprise Proposal Photography: Starting at $600
Includes planning, hidden photographer coverage, and bonus celebration portraits.

Engagement Sessions: Starting at $350
30-90 minutes at one or two locations, all edited images with download rights.

Proposal + Engagement Package: Starting at $600
Both services with package discount. Popular with couples planning ahead.

What Couples Say

From surprise proposals to engagement sessions

1 / 9
1 / 9
See all reviews: Google · WeddingWire · The Knot

Awards & Recognition

Couples' Choice Award 9 Consecutive Years 2024–2016
WeddingWire 5.0 ★★★★★ 127+ Reviews
Google Reviews 5.0 ★★★★★ 116+ Reviews
Premier Bride Magazine 2026 Finalist - Favorite Wedding Pro in the 904

View on WeddingWire | View on Google

Frequently Asked Questions

Common questions about proposal and engagement photography

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. Dozens of 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.

Most couples book engagement sessions 6-9 months before their wedding. This gives you time to use the photos for save-the-dates, wedding websites, and wall art. But there's no wrong time—some couples book sessions right after getting engaged.

Absolutely! Many couples book both with us. After capturing your proposal, we'll do a bonus couples session on the spot. Then, a few months later, we can do a full engagement session at a different location. Package discounts available.