Greg Calley

Captain Greg Calley brings a rare blend of hands-on boating knowledge, technical expertise, and real-world cruising experience to his role as a yacht broker with Massey Yacht Sales. A lifelong boater and licensed captain, Greg has been helping clients buy and sell boats since 2014, earning a reputation for practical guidance, honest communication, and a sharp eye for the details that matter most when choosing the right vessel.

Greg’s background reflects decades of dedication to boats, systems, safety, and seamanship. His credentials include serving as the first U.S. Powerboating Advanced Powerboat Instructor in Florida, American Sailing Association Offshore Instructor, ABYC Electrical Technician, and 200-ton USCG Captain. Before and alongside his marine career, Greg also spent 40 years as an Aviation Maintenance Technician, giving him an exceptional understanding of mechanical systems, electrical troubleshooting, maintenance standards, and the importance of reliability.

Over the years, Captain Greg has sailed many thousands of miles, completed the Great Loop, and operated vessels ranging from small skiffs to 120-foot sail and power yachts. That breadth of experience allows him to speak confidently with first-time buyers, seasoned cruisers, liveaboards, and owners preparing to bring a yacht to market. Whether evaluating a vessel’s condition, discussing cruising goals, or helping a client understand the buying or selling process, Greg brings calm professionalism and practical insight to every conversation.

Clients appreciate Greg’s approachable style, his ability to explain complex technical details in clear terms, and his commitment to matching people with boats that truly fit their needs. His deep mechanical knowledge, extensive time on the water, and passion for the boating lifestyle make him a trusted resource throughout the entire sales process. For Greg, yacht brokerage is not simply about completing a transaction—it is about helping clients move forward with confidence and enjoy the journey ahead.