Rocco "Rocky" "Rocky" Cantalupo

Rocco "Rocky" Cantalupo

October 2, 1935 – August 18, 2025

Rocco "Rocky" Cantalupo, 89, passed away peacefully on August 18, 2025, at his home on Sanibel Island, Florida, surrounded by his loving family.

Born on October 2, 1935, in Port Chester, New York, Rocky was the son of the late Carmine Cantalupo and Dominica "Minnie" Bellantoni Cantalupo. He grew up in Port Chester alongside his beloved sister, the late Marie DeChiara.

Shortly after high school, Rocky met the love of his life, Annette Wilson, beginning a love story that would span 69 years. When Rocky enlisted into the U.S. Army and was assigned to Giessen, Germany, the couple married and moved overseas. The newlyweds lived in Rodgen, Germany, from 1957 to 1958 before returning home to raise their three daughters in Bridgeport, Connecticut, and later Sandy Hook, Connecticut.

Rocky had a long career as an electromechanical designer, but his greatest joy came from his family. In 1998, he and Annette retired to Sanibel Island, where they built their dream home. They became active members of St. Isabel Catholic Church, forming strong friendships and organizing the coffee and doughnuts ministry after Sunday Mass.

A gifted athlete from a young age, Rocky began caddying at local country clubs in Westchester County, NY, including Westchester Country Club, Old Oaks Country Club, and Winged Foot, and later earned the title of caddie master. He quickly stood out as a talented golfer, earning second place in a regional caddie tournament in 1953. As a longtime member of the Dunes Golf & Tennis Club on Sanibel, he continued to enjoy the game well into his 80s, shooting his age of 84 nine times! He eventually achieved the elusive hole-in-one, not once but twice! Rocky was also a devoted New York Yankees fan, sharing his passion with his children and grandchildren, attending games at Yankee Stadium and cherishing the day he sat in a luxury box next to Yankees legend Whitey Ford.

In addition to golf and baseball, Rocky loved basketball. In the 1970s, he launched and coached a youth basketball team for his parish, Our Lady of Good Counsel, in Bridgeport, and later coached at Bridgeport Central High School.

One of the highlights of Rocky's later years was traveling to his father's hometown of Avigliano, Italy, and connecting with distant relatives. Throughout his life, he was fortunate to enjoy several trips back to Italy with Annette.

Rocky will be remembered not only for his devotion to family, his athletic talent, and his deep faith, but also for his humor and gift for making others laugh with spot-on impressions and for hamming it up with his beloved son-in-law, the late Jerry Clowers.

He will be deeply missed by his devoted wife, Annette; her brother Jeff; daughters Candice, Laurie, and Susan; grandchildren Zachary, Nigel, and Christian Leighton, Alexa Clowers, and Rocco Johanson; as well as his cousins and their families.

A memorial gathering will be held at Harvey Engelhardt Funeral and Cremation Services, 1600 Colonial Blvd, Fort Myers from 3:00-5:00 p.m. on Wednesday, August 20 and a memorial Mass will be held at 11:00 a.m. on Thursday, August 21 at St. Isabel Catholic Church on Sanibel. In lieu of flowers, the family requests that donations be made to the St. Isabel Catholic Church building fund.