Born and raised in Berkshire County, Massachusetts, Massimo exhibited a natural talent for drawing from a young age, consistently excelling as an art student. Following high school, he pursued an illustration degree at the Massachusetts College of Art and Design. It was during his senior year, under the tutelage of the legendary plein air painter George Nick, that Massimo discovered his passion for painting. Nick’s methods, emphasizing the simplification of visual elements into basic sections of value and color, profoundly influenced Massimo’s approach to art.

After college, Massimo spent time working on farms in Italy, while maintaining a daily sketchbook and diary. This period of reflection and practice preceded his move to New York, where he embarked on a diverse career in design and illustration. Over the next decade, he took on various roles, from running a branding studio to illustrating books and creating murals.

In 2018, Massimo’s life took a new direction when he met his future wife, based in Miami. Relocating to the vibrant city, he quickly secured a studio space and began freelancing in illustration and mural work. His career flourished as he eventually took on a role as a graphic designer for a renowned studio.

Despite that brief hiatus from painting, Massimo remained engaged with the art scene, particularly inspired plein air painters such as Marc Dalessio and James Gurney, with Gurney being a strong advocate for plein air gouache painting. In 2021, Massimo dedicated a month to creating small-scale plein air gouache paintings, discovering a newfound love for capturing Miami’s everyday scenes. This practice rekindled his passion for painting, leading him to produce nearly 100 works in a single year, the majority painted on site in South Florida, in the tradition he came to love and master: being out in the open under the blue skies.