One of our favorite things as Portland Maine Wedding Photographers is creating engagement sessions that truly reflect a couple’s personality and favorite places. For Dory and Josh, that meant beginning their session at one of their favorite Portland spots: DiMillo’s Floating Restaurant.
From the moment we met up, these two were all smiles and laughter. Their joy is contagious, and it didn’t take long for everyone around them to notice. We started with cocktails aboard DiMillo’s, where they relaxed, enjoyed the waterfront views, and shared stories about their relationship. The setting inspired a different creative direction than we usually take, and we decided to lean into a moody black-and-white editorial style for part of the session.
Some of our favorite images from the evening came from those moments inside the restaurant. Using unique angles, intentional blur from the busy bar atmosphere, and dramatic black-and-white processing, we created photographs that felt timeless and cinematic. One particularly memorable moment happened when Dory and Josh raised their glasses and cheered across the harbor to diners enjoying dinner at Luke’s Lobster. It was spontaneous, playful, and perfectly captured their fun-loving personalities.
After leaving DiMillo’s, we made our way along the waterfront toward Luke’s Lobster. The colorful buoy wall provided the perfect backdrop for some classic Maine engagement photos. We also spent a little time around the stacked lobster traps nearby. Thankfully these were brand-new traps, making them a much cleaner prop than the ones fresh off a working lobster boat! The nautical details added a touch of coastal Maine charm while still keeping the focus on the couple.
From there, we wandered through Portland’s Old Port district, taking advantage of everything that makes downtown Portland such a unique location for engagement photography. We captured some playful images crossing the street near Custom House, using the city traffic and movement to create dynamic photographs full of energy. As the evening continued, we explored the historic cobblestone streets, where the warm city light and brick buildings provided a romantic backdrop for more candid moments together.
What stood out most throughout the entire session was how much fun Dory and Josh have together. Every location, every pose, and every walk between destinations was filled with genuine laughter. Those authentic moments are what make engagement sessions so meaningful and create photographs that truly tell a couple’s story.
As Portland Maine Wedding Photographers, sessions like this remind us why we love photographing in the Old Port. Between the waterfront views, historic architecture, and endless opportunities for creativity, Portland offers the perfect setting for couples who want engagement photos that feel both timeless and uniquely Maine.
We are already counting down the days until Dory and Josh’s wedding at the Samoset Resort next year. If their engagement session is any indication, their wedding day will be filled with even more smiles, laughter, and unforgettable moments. We can’t wait to celebrate with them and continue documenting their story from the cobblestone streets of Portland to the stunning coastline of Rockport.
Dory and Josh, thank you for such a fun evening. We can’t wait to see you both again next year and capture the next chapter of your adventure together!
Portland Maine Engagement Photos
Brittany and Dean are creative Portland Maine Wedding Photographers who loving having fun with our couples. We work together and separately to capture every emotion and angle on your wedding day. Two Adventurous Souls storytelling style will capture your wedding in candid and naturally posed images. Whether you’re looking for a Portland Engagement Session, Costa Rica Wedding or anywhere in New England we will be there for you! For more info please contact us about your wedding photography! Portland Maine Wedding Photographers
