A Boston Engagement Session Through the North End, the Aquarium, and South Station

There are bronze dolphin statues outside the New England Aquarium that have been there forever. Olivia used to climb on them as a kid. She told me that walking up to them, and then she and Thomas spent the next twenty minutes laughing so hard neither of them could hold still for a portrait. I wasn't trying to pose them into anything. I just stayed close and kept shooting while they had their own moment about it. That's the whole idea behind how I shoot engagement sessions. I'm not walking you through a list of poses at a list of pretty places. I'm watching for the second something real happens, and making sure I'm in position when it does.

Engaged couple laughing together in front of the bronze dolphin statues at the New England Aquarium in Boston
Engaged couple sitting together in front of the bronze dolphin sculpture outside the New England Aquarium in Boston
Engaged couple laughing together among the bronze dolphin statues outside the New England Aquarium in Boston

Starting Early: Christopher Columbus Park in the North End

Olivia and Thomas wanted their session to feel like Boston. Not generic skyline Boston. Their Boston. The city they actually live and work in and love. So before we ever picked up a camera, we sat down and went through my portfolio together, pulling images that felt like them. That conversation is where this whole day got built.

It's also where I found out the World Cup was in town that week.

Which meant downtown Boston was about to become a sea of jerseys, flags, and a few thousand people trying to catch a train to the stadium. Beautiful chaos. Terrible for portraits. So we got ahead of it and started at Christopher Columbus Park in the North End before the city woke up.

That park has this long covered trellis that does something strange to you. You walk into it from the city and for a minute you're somewhere else entirely, somewhere green and quiet, before it spits you back out into Boston again. Olivia and Thomas are goofy together in the best way, and that first stretch of the morning was just them being exactly that. Laughing at nothing. Chasing the good light. No nerves left by the time we hit stop two.

Engaged couple laughing together under the trellis at Christopher Columbus Park in Boston's North End
Engaged couple standing under the wisteria-covered wooden trellis at Christopher Columbus Park in Boston
Groom-to-be kissing his fiancée's cheek near Christopher Columbus Park in Boston's North End
Engaged couple embracing under the wooden pergola arch at Christopher Columbus Park in Boston

Engagement Portraits at the New England Aquarium and Rowes Wharf

After the aquarium, we kept moving south along the Harbor Walk toward Rowes Wharf Plaza, one of the newer parks built out of the Big Dig, with the Custom House Tower and the skyline sitting right behind it. We had the entire place to ourselves. So we used all of it. Running. Jumping. The kind of kissing that makes you feel like you're intruding on something, in the best way. When a couple has that much energy and nowhere to put it, my job is just to stay out of the way and keep shooting.

Engaged couple holding hands and walking along the Harbor Walk near Rowes Wharf in Boston
Engaged couple laughing while he spins her around near Rowes Wharf in Boston
Groom lifting his fiancée for a kiss during their engagement session near Rowes Wharf in Boston
Engaged couple embracing with the Custom House Tower and Boston skyline behind them during their Rowes Wharf engagement session

South Station: A Boston Landmark, Right in the Middle of the Action

By the time we reached South Station, the World Cup crowd we'd woken up early to avoid had fully arrived. Hundreds of people in national jerseys lined up for trains to the stadium. Police managing the flow. Actual, real Boston noise and motion, right behind two people standing still in front of one of the most iconic facades in the city.

I wasn't mad about it. That contrast is the shot. Two people completely locked into each other while an entire city rushes past them trying to catch a train. That's not a backdrop I could have planned. That's Boston showing up exactly when it needed to.

That's the thing about this work. You can plan the where. You can't plan the moment. You just have to already be looking when it shows up.

Olivia and Thomas, your wedding is going to be so much fun to shoot.

Engaged couple laughing together near South Station in downtown Boston
Groom lifting his fiancée and spinning her near South Station in Boston
Engaged couple embracing outside South Station's clock tower with World Cup crowds and event barricades in the background
ARE YOU RECENTLY ENGAGED?


Hi, I’m GreG,

Boston wedding and engagement photographer.


If you’re dreaming of engagement photos that feel personal, cinematic, and true to your love story than you’re in the right place!

I’ve photographed hundreds of couples across Boston’s most iconic locations (and plenty of hidden gems, too), and I believe that your experience should feel just as good as the images look. Let's connect, I'd love to hear about your ideas for your Boston engagement and wedding day!