Richard D. O’Leary, 88, passed away peacefully surrounded by his loving wife, Barbara, three daughters and three stepdaughters on Saturday, April 17, 2021.

Richard was born in Lewiston, the only son of an Irish immigrant. He was raised in Auburn, attended the Maine Maritime Academy in Castine where he earned a Bachelor of Science degree. He also completed the Alexander Hamilton Institute’s course in modern business. He went on to receive a graduate tuition scholarship from Adelphi University where he earned a master’s in business degree and was awarded an honorary Doctor of Science Degree from Maine Maritime Academy, as well as being one of the first 12 inductees into that institutions Wall of Fame.

After service in the U.S Navy, the U.S. Merchant Marine, where at the age of 25, was the second officer and navigator of the SS United States, making 254 transatlantic crossings from New York to Europe. He then became Commander of Midshipman at the U.S. Merchant Marine Academy at Kings Point, N.Y. Richard then moved to Norfolk, Va., and became the assistant general manager of the Norfolk Port and Industrial Authority. In 1972 he founded Cruise International/ CI Travel which grew to become a national company with 2,500 employees and 55 offices in 12 states. He built, owned and operated a fleet of 14, 600-passenger, harbor cruise vessels in the major port cities throughout the United States, including The Spirit of Norfolk, with Barbara, at his side.

They retired in 2005 and resided in Ogunquit, in the summer and Naples, Fla., in the winter.

Richard is survived by his wife, Barbara, of 45 years; his daughters, Lauren O’Leary, Leslie Quisenberry, Megan and Don Mayer; stepdaughters, Michele and Greg Heckman, Stephanie and Woody Prettyman, Danielle and Russ Primack; 12 grandchildren; two great-grandchildren; and four nieces. Richard was predeceased by his stepdaughter, Dione Noel Boecker, who passed away Aug. 18, 2016.

The family wishes to extend its heartfelt appreciation to Kindred Hospice of Virginia Beach and all the wonderful caretakers especially Heather Blank and Father Crisanto of St. Mary’s Catholic Church of Virginia Beach.

We honor his memory, mourn his loss and celebrate his legacy.

Richard will be laid to rest in Kennebunkport, at Arundel Cemetery on 11 a.m., Saturday, May 22, 2021.

To share a memory or leave a message of condolence, please visit Richard’s Book of Memories Page at