Pineapple Point combines luxurious South Florida charm with unmatched service for its gay male clientele. Since it opened its doors, this approach has influenced every aspect of the Pineapple Point guest experience, thanks to owners and founders Judd Chapman and Phil Quattrone, who are truly hands-on.
Their careers in the airline and advertising industries took them all over the world. During this time, they searched for the perfect place to stay. They ultimately found it in a 1930s old-world Florida property, originally designed as a guesthouse. Judd and Phil’s talent is well known for building and restoring unique architecture. Their zeal and luxury-minded approach played a key role in returning this gated tropical paradise to its original charm and splendor.
Since 1999, Pineapple Point has grown in size, accommodations, and popularity, always with an eye toward an exclusive, luxurious, and unparalleled experience for guests.

“We are committed to providing our guests with a luxurious and relaxing atmosphere through consistent service of the highest quality.
Good customer service begins, and flows, from the top. As owners, we run our business by this rule, but above all…we know that a good employer takes good care of his employees… they will then, in turn, take good care of his customer. We’ve earned our reputation largely because of our staff. Our guests tell us, over and over again, that they are the best around.
Together, we look forward to welcoming you.”

Judd Chapman & Phil Quattrone


  • Judd Chapman, Proprietor
  • Phil Quattrone, Proprietor
  • Scott Messner, General Manager

Judd was born in Henderson, Kentucky, a small town on the Indiana/ Kentucky border. He graduated from the University of Kentucky in Lexington, and moved to South Florida shortly thereafter. Judd excelled as an advertising executive for BellSouth, until the inception of Pineapple Point in 1999. During their 22 years together, Judd and Phil have purchased and renovated dozens of properties, mostly in the Victoria Park and Colee Hammock neighborhood of Fort Lauderdale. Together, with his advertising and business backgrounds, Judd has earned a reputation as one of Fort Lauderdale’s premiere land developers. For years he was in the primary business of land purchase, and the construction of high end, homes and townhomes. As a result, he brings an added bonus to those of our guests looking for South Florida real estate investments. He is a licensed Florida Real Estate Sales Agent, working for the sales team of “The Gayle Borden Group” of Coldwell Banker Real Estate, Inc.

Born and raised in Syracuse, New York, Phil graduated from Saint Leo University, in Saint Leo, Florida. After beginning his career as a Flight Attendant for a major U.S. Carrier, he moved from the northeast to South Florida. His 23 years in the airline industry afforded him numerous titles of distinction. In addition to being a Cabin Service Director and Purser on International flights, Phil also held several other key Customer Service Training positions. Designing and implementing all aspects of new onboard services, as well as holding numerous human resource titles, gives Phil an advantage over competitors in running a successful business. Among his many fortes, his status as a Customer Service Training Specialist is evident in his unending resolve for a customer service level at Pineapple Point that is second to none.

A native of Madison, Wisconsin, Scott began his career at Pineapple Point as a staff member in 2007. In 2014 he was promoted to general manager. Scott is a graduate of the University of Wisconsin, with a degree in landscape architecture. He has lived in Sydney, San Francisco and Cape Cod. As a longtime Pineapple Point employee, he brings a history of superb customer service skills and a reputation of great leadership to his position

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