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Phil McCabe Named Naples Parade Grand Marshall


Born in 1947 in the blue collar neighborhood of Dorchester in Boston, Massachusetts, Philip Joseph McCabe was literally raised in the attic of his parents’ overcrowded one-bath home, along with his five siblings. At the age of 19, with the Vietnam War nearing its height, Phil left to join the Air Force, never to return to his native Boston.

While overseas, Phil worked in the field of intelligence, becoming a specialist in the analysis of the Russian missile space program during the Cold War. For his services, he received an honorable discharge from the Air Force after serving four years, primarily in Pakistan and Afghanistan. Upon his discharge from the Air Force, Phil was given the opportunity to join the Central Intelligence Agency. He accepted their offer, and after training at CIA headquarters, was stationed in northern Iran, directly on the border with Russia. During his next four years working overseas, Phil saved every penny he could, knowing he was not meant to be a career CIA employee. In 1975, he resigned his position with the CIA to pursue his real passion – entrepreneurship.

Phil soon returned to his New England roots, ending up on the Maine coast. It was there, at the age of 29, that he used all of his savings – $25,000 – to purchase a bankrupt lodging business on the beach. Phil had found his calling and busily set about growing his new business, heading down a path that would lead to a lifetime of entrepreneurial success.

As he worked to restore the bankrupt property, Phil’s fortunes grew steadily, culminating a decade later in a multi million dollar enterprise. After a dozen years of operation, Phil decided to expand his hospitality business in the Sunshine State. After painstaking research, he set his sights on Southwest Florida, sold his accumulated Maine holdings, and brought his earnings to Naples, Florida.

Building on his early success, and with a keen eye for opportunity, Phil found and purchased several acres of land in north Naples, with the ambition of building his first boutique hotel. In 1986 he opened the Inn of Naples, a small boutique property with a restaurant. It was an instant success. After six years of operation, Phil built a second boutique hotel called the Inn at Pelican Bay, which was also an immediate success. Another six years later, still with boundless energy and ambition, Phil converted an old bank building in downtown Naples where he developed and opened the Inn on Fifth, still an extremely successful enterprise today. For 15 years the elegant Inn was home to McCabe’s Irish Pub & Grill, a favorite local watering hole that became a Naples institution.

In addition to the wildly popular McCabe’s Irish Pub & Grill, Phil has built, opened and operated several other successful dining establishments, including Garden Court Café, Windows on the Water, McCabe Brothers Steak House, Boston’s Restaurant & Sports Bar, and his newest venture, Avenue5. His new upscale Avenue5 restaurant and the boutique Inn on Fifth are landmarks in Naples, having been recognized in travel and culinary publications worldwide.

After accumulating land and buildings, and developing and managing numerous commercial and residential properties, Phil’s instincts, vision, energy and years of success in Naples enabled him to initiate one of the most significant projects of his career.

In December 2012, the Inn on Fifth put the finishing touches on an $18 million expansion project, which added new luxury suites and meeting and retail space, and a $1.7 million renovation which completely redesigned the look and feel of the property. The largest redevelopment effort on Fifth Avenue South since the start of the 2008 financial crisis, the milestone project involved the construction of a new three-story, 40,000-square-foot building directly across from the Inn’s familiar Fifth Avenue South location. The building includes 32 Club Level Suites, an executive boardroom, and 12,000 square feet of retail space on the ground level, anchored by Chase Bank and Boston Proper, a division of Chico’s. Part of Phil’s vision and care for the community was to improve all of the streets around the new expansion with better street lamps and landscaping. With its elegant, contemporary feel and prestigious Forbes Four-Star rating, the Inn’s Club Level Suites set a new standard of luxury on trendy Fifth Avenue. The Inn on Fifth has also earned high acclaim following the expansion and renovation, including AAA Four Diamond, Conde Nast Johansens and Forbes Four-Star Travel rating.


It was in 2014 that Phil combined his vision with the talents of world-renowned designer Jeffrey Beers International to create Avenue5, a new luxury restaurant at the Inn on Fifth. With seating for 240 guests in a vintage glam atmosphere, the $3 million Avenue5 features a stunning island bar, private dining rooms and a phenomenal culinary team, befitting the higher standard of excellence and elegance Phil had created at the Inn.

Phil’s latest vision has led to two new projects that will bring more dramatic change to downtown Naples: The Inn on Fifth Residences, a standalone five-star property with 51 suites and 54 condominiums; and Fifth and Fifth, a half-acre, mixed-use development of luxury residents and retail space, located directly on Fifth Avenue South. In addition to these Naples projects, Phil is reaching back to his Maine roots where he started his entrepreneurial career. He has recently assembled more than 60 contiguous acres in the prestigious Cape Arundel neighborhood in Kennebunkport, Maine, where he plans to develop residential homes.

Along the path of hard work and success, Phil has been blessed with two sons – Philip, 18, and Joseph, 20. Phil instills in his boys the importance of giving back to the community, doing so by example. Thus far, he has awarded more than 70 scholarships to worthy Collier County students through the “Take Stock in Children” program of the Collier Education Foundation, one of his favorite charities. Phil is also a major donor to the Community School of Naples, where his sons attended. He also supports many other area non-profit and cultural organizations, such as the Community Foundation, the Gulfshore Playhouse, the Naples Community Theater, and Fun Time Academy.

As a former board member of the Chamber of Commerce, Phil was instrumental in the relocation of the Chamber from a dilapidated building into a new, world-class facility. He then facilitated the relocation of the Chamber Visitor Center into its highly visible successful current location on Fifth Avenue South. He was former chair of the Community Redevelopment Agency in the city of Naples, guiding the city through some dramatic changes, such as residential zoning within historically commercial parts of the city that had been failing, and bringing miles of landscape beautification to city and county medians. He was also among the original group of volunteers to extend the landscape beautification of the entire county.

Phil was a major advocate for creating a city of pedestrian-friendly streets, sidewalks and connectivity. He has served on numerous boards, including the Collier County Community Redevelopment Agency, helping implement similar changes to struggling parts of the county. His other board involvement includes leadership roles with Naples Better Government; the Remington Association; the Ritz-Carlton Bachelor Gulch Association; the Heart of Naples Committee; the Bay Colony Association; the Arrabelle at Vail, Colorado; and the Fifth Avenue South Business Improvement District. Phil is currently president of the Business Improvement District Owners’ Advisory Committee, and was named Man of Distinction for being a community leader and advocate for high-risk children. Junior Achievement of Southwest Florida also chose Phil to be inducted as a laureate into the 2012 Business Hall of Fame of Collier County.


While driven by a fierce entrepreneurial spirit, Phil McCabe has always cared about his community, never failing to share his time, talents, and resources where most needed, and helping to deliver some of the highest quality development projects in Naples.

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