If you’re dreaming of a surprise engagement in St. Augustine, there’s no better backdrop than the glow of Nights of Lights. The twinkle of millions of lights, the historic charm, and the romantic coastal air make it one of the most magical places in Florida to propose.
But as breathtaking as it is… it’s also one of the busiest times of the year. And with high traffic, heavy crowds, and limited availability, many couples run into the same avoidable mistakes.
To help you plan a smooth, memorable, and stress-free proposal, here are the most common mistakes people make—along with tips to avoid them.
Tips from a St. Augustine Proposal Photographer
1. Not Accounting for Parking and Traffic
Let’s be honest—Nights of Lights traffic is no joke. During peak dates, the closer you get to downtown, the slower everything moves. Add the pressure of timing a proposal, and things can get chaotic fast.
Why this is a problem:
- You may miss other plans, such as dinner reservations.
- You might get stressed (which your partner can immediately sense).
- If you hired a photographer, they’re already waiting at the location… so you risk being late or losing the perfect lighting.
How to avoid it:
- Arrive at least 45–60 minutes early.
- Park in the parking garage or on the outskirts to avoid circling endlessly.
- Uber in if you can so you don’t have to hunt for a spot.
- Plan to walk—St. Augustine is very walkable once you’re parked.
2. Not Planning Around the Crowds
A proposal during Nights of Lights means one guarantee: crowds will be there. They’re part of the experience. The key isn’t avoiding them—it’s working around them.
Why this is a problem:
Many people imagine a quiet, empty romantic moment… only to arrive and see hundreds of people lining the streets. They get overwhelmed, freeze, and lose the spot or timing they wanted.
How to avoid it:
- Choose strategic times:
• Weeknights
• At sunset before peak crowds
• Later at night when the streets calm down - Pick locations that photograph beautifully even with people walking by.
- Give yourself flexibility—don’t lock yourself into one exact spot if it’s crowded.
A professional familiar with the area (like a St. Augustine proposal photographer) can guide you to lesser-known angles that still capture the magic of the lights.
3. Not Making Dinner Reservations Early
After you propose, chances are you’ll want to celebrate with a beautiful dinner. The problem? During this season, restaurants book out weeks in advance.
Why this is a problem:
- You may end up waiting hours for a table.
- You might have to settle for a place that doesn’t fit the vibe you imagined.
- The post-proposal glow deserves a good meal—not rushed takeout.
How to avoid it:
- Make your reservation as soon as you pick your date.
- Romantic favorites fill up first—places like Columbia, SAINT, Forgotten Tonic, and Old City House.
- If you’re proposing before dinner, reserve earlier. If after, go for a later time to avoid rushing.
4. Having a Ring Box That’s Too Bulky
This one surprises a lot of people.
Jewelry stores often give ring boxes that are beautiful… but also enormous. Trying to hide that square bulge in your pocket? Nearly impossible—especially if you’re walking around or taking photos.
What happens:
Your partner sees it, gets suspicious, and suddenly the “surprise” part of the surprise engagement is gone.
How to avoid it:
- Buy a slim ring box—there’s so many to choose from on Amazon! And it’sn easy to hide.
- Slip it into:
• A jacket inner pocket
• A sock
• A travel pouch - Practice removing the box smoothly so you’re not fumbling in the moment.
This single change saves so many proposals.
5. Not Considering Hours and Required Permits for Certain Locations
Another detail that often gets overlooked during Nights of Lights proposals is that some of St. Augustine’s most iconic spots have specific operating hours—or require permits you might not know about.
When people assume every location is open, accessible, and permission-free, they can run into unexpected obstacles right before the big moment.
For example, the Koi Pond at the Lightner Museum is frequently suggested on Reddit and Facebook as a proposal spot. However, this pond is located in the museum’s courtyard, and it requires a paid permit if you’re hiring a professional photogrpaher. It also has restricted hours, which can make timing tricky. A professional photographer experienced with St. Augustine locations can help secure the permit and plan around the schedule to ensure everything goes smoothly.
Why this becomes a problem:
- Some parks, courtyards, and historic sites close at dusk or have limited nighttime access.
- Certain city-owned or museum-owned areas require permits for professional photography.
- Security or staff may ask you to move if you’re somewhere restricted—even if you’re seconds from proposing.
- Lights may turn off earlier at less popular spots, leaving the area darker than you expected.
How to avoid it:
- Research your chosen location’s hours ahead of time.
- Double-check if a photography permit is required (some do, some don’t).
- Work with a photographer who already knows the rules—they can guide you to spots that don’t require permits and stay open later.
- Always have a backup location nearby in case your first choice becomes inaccessible.
When planning a surprise engagement in St. Augustine, the last thing you want is a security guard interrupting your proposal or finding out that your perfect spot closed 10 minutes ago.
A little preparation ensures you can enjoy the moment—without the stress or last-minute scrambling.
6. Not Hiring a Trusted Photographer — Especially for Night Photography
This is one of the biggest mistakes people make during Nights of Lights proposals.
Photographing this event is not like shooting a regular daytime session. The lights are stunning, but they create extremely challenging conditions: low light, strong backlighting, heavy crowds, and fast-moving moments you only get one chance to capture.
Because of this, not every photographer is prepared for a proposal—especially a nighttime one.
Why this matters:
- Some photographers don’t specialize in low-light work.
- Many don’t know St. Augustine’s layouts, angles, and crowded choke points.
- Proposals happen fast—there’s no redo.
And here’s the part most people don’t expect:
We commonly receives last-minute phone calls from people whose photographers have bailed just hours before their proposal.
- It happens more often than you’d think.
- Sometimes the photographer realizes they can’t handle shooting at night.
- Other times they get overwhelmed by the crowds.
- And occasionally… they simply don’t show up.
When that happens, couples scramble to find a professional who:
- Knows St. Augustine well
- Can shoot confidently in the dark
- Can still capture the moment beautifully with almost no prep time
That’s why hiring a trusted, experienced St. Augustine proposal photographer from the start is so important—especially someone who understands Nights of Lights and has successfully photographed dozens of surprise engagements under these exact conditions.
A seasoned photographer won’t just take photos—they’ll help you plan the logistics, navigate the crowds, and guide you to the best-lit spots so your proposal looks magical instead of chaotic.
Final Thoughts
A surprise engagement in St. Augustine during Nights of Lights is one of the most magical, memorable experiences you can plan. With a little preparation—and by avoiding the mistakes above—you can create a proposal that feels effortless, romantic, and unforgettable.
If you’re ready to plan the perfect moment, work with someone who knows the city, knows the season, and knows how to capture the glow of the lights beautifully.
St. Augustine gives you the magic. You just need a plan to make it come together. ✨
Phavy Photography (phavyphotos.com)
St. Augustine Proposal Photographer <– click here to see more of my work and proposal information
E-mail: contact@phavyphotos.com
Phone: 904-228-1350
