In the early 1990s, Santo pivoted his artistic focus toward sculpture and painting. Drawn by Italy’s rich artistic heritage, he moved his family to Florence in 1996, eventually settling in the medieval village of Pietrasanta on Tuscany’s northern coast. This historic town, a cradle for artists and sculptors since the 15th century (notably fostering Michelangelo's work), became his spiritual home, deeply influencing his monumental and emotionally resonant human figure sculptures. Inspired by the likes of Michelangelo and Bernini, Santo's work, often monumental in size and infused with delicious ambiguities, transcends time by bridging ancient classical sculpture with Renaissance and contemporary aesthetics. This singular achievement has been recognized by over 50 internationally acclaimed citations.

Santo's artistic leadership also extends to his role as creative director for the film and media school Full Sail and its associated production company, Platinum Post. His sculptural commissions include significant works for Nike, Toys 'R' US, Wells Fargo, and public spaces. The Wells Fargo Center for the Arts in Santa Rosa, California (now the Luther Burbank Arts Center), commissioned two striking 18-foot canvases from Santo’s "Spring Load Series" for its lobby, showcasing his finely tuned sense of balance through geometric paintings.

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His works are held in the permanent collections of prestigious institutions worldwide, including the Copelouzos Family Museum in Athens, the Sprengel Museum in Hannover, Germany, the Polasek Museum in Winter Park, Florida, the Dillon Collection, the Metropolitan Museum of Art, and the Bozzetti Museum, among others. His monumental Torso 175 was placed in the city of Pietrasanta, Italy in 2005. Santo’s work is listed in the Italian National Directory of public sculptures. Santo was also the artistic director and sole artist commissioned to create 10 original works for the Cloister at St. Patrick's in Anchorage, AK. This collection at St. Patrick’s includes the "Pieta for the New Generation," completed in 2014. The “Pieta for the New Generation” bronze sculpture, depicting the sorrowing Mary, has garnered significant national and international press attention. Santo was also commissioned by the New York Racing Association, Churchill Downs, and the Stronach Racing Group to create the new, iconic, and largest Sports trophy in the world, the “Triple Crown Trophy”. Santo also created the Breeder’s Cup Trophy for the same organization. In 2016, Art Knokke, in Belgium, chose Santo as its featured artist for the "Exhibit on the Sea".  The show had 10 monumental sculptures of Santo’s greatest works. His numerous accolades include awards from the United States Olympic Committee, the Florida Film Festival, De heer Zeilstra in the Netherlands, and the Douglas Dillon Foundation.

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Santo continues to exhibit his work internationally, with notable recent shows including the prestigious Villa Franca exhibition in Verona, Italy, where his monumental works were displayed around the city and the Castello Scaligero.

Now, Roberto Santo is embarking on a pioneering new chapter: his highly anticipated entry into the NFT world, with the launch of his "Woosh" NFT collection on Open Sea January 13, 2026. Santo brings his signature vibrant color and dynamic style to the blockchain. This limited series of 999 unique digital editions offers collectors an opportunity to own a piece of his artistic legacy in an entirely new and innovative format, bridging his celebrated traditional and photographic career with the future of digital art. Santo continues to divide his time between Italy and America, perpetually pushing the boundaries of artistic expression.