In 1986, he was approached by New York real estate developers Tony Goldman and Mark Soyka who wanted to renovate the storied but run-down Park Central Hotel on Ocean Drive in Miami Beach. Robins represented his father at the meeting which devolved into a discussion about renovating South Beach. (Robins states that Goldman was "the second big influence on my career, after my father.") In 1987, Robins branching out on his own, formed Dacra Development, Inc. and started to purchase and develop South Beach real estate. In 1988, he formed Dacra Construction and his brother Scott also got into real estate forming a separate company, Scott Robins Companies, Inc. which partnered with Craig's company. Robins brokered a compromise between developers and preservationists over expanding Miami Beach's Art Deco Historic District which helped establish his reputation as a preservationist. In the early years of his career, Robins was mentored by his then-business partner Chris Blackwell, founder of Island Records. Together, they renovated a number of properties on South Beach which were repositioned as Island Outpost hotels. Those properties included the Netherland, the Leslie, the Kent, the Cavalier and the Marlin, which was widely credited as igniting the renaissance of the area. In 1992, they purchased with their father for $8.5 million the Cavalier, the Cardozo, the Carlyle, the Leslie, and the Victor hotels from the creditors of developer Leonard Pelullo. Robins’ next important mentor was real estate developer Tony Goldman, who was largely credited for the revitalization of NYC’s Soho. In 1997, Robins bought Chalk's Airlines and renamed it Pan Am Air Bridge; he sold it in 1998. In 1999, Dacra acquired 8.5 acres on the southern tip of Allison Island and created AQUA, a New Urbanist community featuring modern architecture, design and site-specific public art. The private residential community of 46 homes on Allison Island designed by ten different architecture firms with a master plan by Duany Plater-Zyberk and public art projects including a 100-foot mural by Richard Tuttle. It is now an international model for development. Thereafter, Robins focused on reviving Miami’s Design District. In 2005, Robins launched the first Design Miami collectible design fair in the Design District alongside Art Basel. A global forum for design, each fair brings together influential collectors, gallerists, designers, curators and critics to celebrate design culture and commerce. Occurring alongside the Art Basel fairs in Miami, USA each December and Basel, Switzerland each June, Design Miami/ has become the premier venue for collecting, exhibiting, discussing and creating collectible design. The Miami Design District is now evolving into a luxury shopping center with offerings including Louis Vuitton, Hermès, and Cartier. In 2012, the District became the only project in Miami Dade county to receive LEED Gold Neighborhood Development certification.

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