This was a landmark session for me, as it was the first Newport Vineyards proposal I have photographed in the rain. Typically, outdoor shoots are rescheduled when the weather is less than optimal, but with Joe and Casey visiting from out of state, this Newport Vineyards proposal was going to happen regardless of the downpour.

Drawing on my background in sports photography, working in wet conditions is a breeze for me. However, this particular Newport Vineyards proposal did present a few unique challenges:

• Could Joe persuade Casey to venture out into the vineyard in the rain?
• How could I hide in plain sight in a deserted vineyard during inclement weather?

Joe’s sister, Deanna, coordinated the Newport Vineyards proposal with me. This partnership was essential, as we were able to text updates regarding the progress of lunch and the state of the weather without alerting Casey.

I arrived for the Newport Vineyards proposal about 30 minutes after their lunch reservation began, and it was raining quite hard. I advised Deanna to bring an umbrella and encourage the couple to take a post-lunch walk. While sitting in my car looking out at the empty grounds, I tried to figure out how to follow them in my bright red jacket without being spotted. Making this Newport Vineyards proposal a surprise was not going to be easy.

At the appointed time, I received a text stating they had ordered another charcuterie board. I certainly couldn’t blame them for wanting to stay dry. I waited patiently until I finally received the notification that they were heading out.

Just before they emerged, I opted to leave my backpack behind and carry only my sports bag to conceal my primary camera. I walked up to the vineyard’s information sign and pointed at the map as if I were a tourist looking for directions. Out of the corner of my eye, I spotted the couple—the only people outside—closely followed by Deanna and her family, who provided excellent cover.

I sneaked up behind the family group as they walked. Just as the couple ventured down an aisle of vines, I struck up a normal conversation with Deanna to maintain my disguise. As we talked, I kept my eyes on Joe; the moment he began to kneel, I pulled out my camera and captured the Newport Vineyards proposal.

Casey and Joe were completely shocked and had no idea where I had come from. With the mission accomplished, we transitioned into a mini-engagement shoot. We all got a bit wet, but the rain could not dampen the joy of this successful Newport Vineyards proposal.