How Photographing Skylines Made Me a Better Photographer

How Photographing Skylines Made Me a Better Photographer

Photographing skylines and cityscapes takes a lot of technical ability, both in knowing what gear to bring and how to capture a variety of lighting conditions. Many photographers have made careers out of perfecting this genre, taking it even further by mixing in astrophotography, light painting, and even motion. Whether you're looking to explore your own backyard or get more out of traveling, shooting skylines can open your eyes to new possibilities no matter what type of photography you shoot.

Early in my career, I fixated on commercial work, setting up elaborate studio shoots, spending hours on lighting diagrams, and planning out every detail. I was working towards having my own studio space and bigger and better-budgeted clients. At this time, this is all my photography was. I didn't carry a camera with me everywhere. I didn't take one when I traveled for vacation. That's just not the type of photographer I saw myself as. In the studio with lots of gear and a plan was my photography. That's where I was in control, and though I was growing my business, I couldn't see the walls I was putting up around myself.

Boston Skyline seen from the waterfront.

Like a lot of photographers, I split my time in the beginning between assisting and my own clients. I took all kinds of assisting work around Boston and NYC, working for lots of different types of photographers. I credit these experiences (good and bad) as one of the best tools for learning how to be a professional and run a business. Eventually, I started working with Nikon Legend Lou Jones who introduced me to shooting skylines.

I remember the first time I traveled with Lou as an assistant. I believe it was Dallas, TX. We landed, picked up the rental car, and immediately drove to the city limits to an open park with a beautiful view of the skyline. It wasn't part of the assignment, and I was tired from the trip, not understanding why we were doing this before even checking in at the hotel. I traveled all over the country that first year watching as he set up his tripod at each new city to get another shot, still not seeing the value in it. Then, one day, I picked up a camera and set up next to him.

Rio de Janeiro viewed from Sugarloaf.

It wasn't about the images we shot but the adventure of finding those shots, exploring each city for the perfect viewpoint and finding new ways to see it even if it had been photographed a million times before. I applied all my skill in planning a new challenge. You can plan out the location, even the time of day, but not the weather. Not what you would see when you finally arrived. We often had one chance at a skyline before we flew off to the next assignment. So, you had to get what you could with what was available. Sometimes, you didn't have time to be there at sunset or stay long enough for magic blue. Other times, you would wait for hours for the perfect time when lights are coming on and the sun is setting just to have a street light not working.

San Fransisco skyline viewed from Twin Peaks.

I would spend hours on Google maps pinpointing the exact spot a photo of a skyline was taken then searching nearby buildings and streets for better vantage points. I chatted on forums with local photographers looking for tips on interesting buildings and monuments. When I was home I started exploring surrounding areas to shoot great views of Boston. I began to plan locations I wanted to photograph when I would travel with friends or family. Every trip no matter the reason was another opportunity to shoot a new skyline or try a different spot.

Indianapolis skyline viewed from Indiana State Museum.

What I didn't realize at first was over the years, while I continued shooting studio work, how I approached new jobs was evolving and moving out of the studio. I began location-scouting more and finding reasons why shooting in the studio wouldn't work. I carried a camera and started building a library of skies and clouds for post. I paid more attention to how the light affected my surroundings at different times of day. I looked up and over my shoulder when walking around. Basically, I started seeing photography as more than the walled-in little studio I had detailed control over.

Boston skyline

I still shoot elaborate studio assignments and love working in that way. However, without skylines, I never would have started shooting editorial work, which led to travel work. I probably wouldn't be taking my work in a new direction and shooting adventure and lifestyle assignments. Without even knowing it, skylines became a personal project that led to new interests as well as new job opportunities. We as photographers always hear about how important personal projects can be. There are several articles here on Fstoppers about it. For me, it wasn't a plan, it was just something I was doing. It was almost like a hobby outside of my work.

Several years back, I helped create a tutorial video on photographing skylines for Lou Jones. After working with Lou for many years, he became a sort of mentor to me, another tool that is important in learning the industry. In this video, he gives lots of valuable tips he has used shooting skylines all over the world during his lengthy career.

Also check out Fstoppers' own tutoria,l “Photographing the World: Cityscape, Astrophotography, and Advanced Post-Processing,” with Elia Locardi, which contains everything you could possibly want to know about taking your skylines to the next level. After seeing Elia’s work, I was inspired to start trying to add astrophotography to my cityscapes.

Michael DeStefano's picture

Michael DeStefano is a commercial/editorial photographer focusing on Outdoor Lifestyle and Adventure. Based in Boston, MA he combines his passion for outdoor sports like climbing and surfing into his work. When not traveling or outdoors he is often found geeking out over new tech gadgets.

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Great article Mike!

Really nice story mate, thanks for sharing!

I had a yearlong skyline project: photographing the sunrise over Columbia, South Carolina, US from the Lake Murray Dam on the first solstice and equinox. Since it was time-bound, I was limited to the dates. I used a 28mm lens and B&W film to capture the skyline of Columbia.
The winter solstice was brutal. Winds were gusting about 45 MPH off the lake. Fortunately, my back was to the wind. There is a pedestrian walkway across the dam and I was the only fool on the dam at that time. I would have to take off a glove to fire the shutter.

That sounds amazing. Ive definitely spent many nights getting that perfect shot freezing or in the rain/snow.