Disney Engagement Photographer | Caroline & Matt at the Boardwalk

As a Disney engagement photographer, there’s nothing better than working with couples like Caroline & Matt—sweet, stylish, and totally in love. These two are tying the knot this May at one of our all-time favorite venues: Disney’s Wedding Pavilion! They booked one of our full photo and video collections, which includes a complimentary one-hour engagement session, and I’m so glad they took full advantage of it.

Why Engagement Sessions Are the Secret Sauce

Engagement sessions are more than just pretty photos. They’re our one chance to hang out before the wedding day in a relaxed, no-pressure setting. It’s the perfect way for us to build a connection, shake off any camera nerves, and practice posing together so everything feels natural on your big day.

It also gives me a chance to see how you interact as a couple—whether you’re super cuddly, goofy, shy, or full of PDA—so I can tailor my posing direction to you and capture the most genuine, real moments possible.

Dreamy December Weather + Disney Magic

Caroline & Matt were super smart and scheduled their shoot during the cooler Florida months. We had a beautifully overcast, breezy December day—dream conditions for a photoshoot! They wanted a soft, romantic Disney vibe, so we chose Disney’s Boardwalk Inn Resort, one of my favorite engagement photo locations near Walt Disney World.

We explored the best photo spots around the Boardwalk, including:

• The iconic “Vacation Sensation” mural

• Atlantic Dance Hall

• Sea Breeze Point gazebo

• The Yacht & Beach Club lighthouse and gardens

We managed to make it all the way around the lake in just one hour (yes, I move fast!), and the variety of backdrops made it feel like five locations in one.

Pro Tip: Pair Your Hair & Makeup Trial With Your Engagement Shoot

Caroline also booked her hair and makeup trial with the amazing Stacie Otto on the same day as their session, which I always recommend when possible. Why waste a great glam look? Most artists are happy to slightly tweak the style between the trial and shoot so you can get the best of both worlds.

Wardrobe Goals: What to Wear for a Disney Resort Engagement Session

Let’s talk outfits—because these two nailed it. Caroline wore a soft floral dress that flowed beautifully and popped against the Boardwalk’s pastel backdrops. Matt kept it simple with a light blue button-down and grey slacks. Their look was cohesive, neutral, and timeless without being boring—exactly what I recommend for couples doing sessions at Disney resorts. Pro tip: avoid loud patterns or super dark colors, especially in dreamy, light-filled settings like this.

Candid, Romantic & So Much Fun

I had the best time wandering Disney’s Boardwalk with these two. They followed my posing prompts like total pros, and I honestly could’ve kept shooting all day. Their chemistry made everything feel effortless, and I think that shows in the photos.

Here are just a few of my favorite images from their romantic Disney engagement session. Don’t they look like they were made for this place?