Alan E. Lewis, travel industry executive and philanthropist, dies at 74

Leaving college after a year, he got a job as a lifeguard in Miami, where he made headlines saving a swimmer’s life. His father visited soon after and was unimpressed at the heroics.
“I was rebellious and ran with some rough company,” Mr. Lewis later wrote , “and I got into trouble at every turn.”
By his own description, Alan Lewis’s youthful years in Boston were eventful and unsettled. His parents split up when he was an infant in Dorchester, and while living with his mother, he moved 14 times in seven years.
“We got into a huge argument over the direction in my life,” Mr. Lewis wrote in “Driving With No Brakes,” a 2010 memoir. “Actually, it was over its lack of direction. Was I going to be a lifeguard for the rest of my life?”
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Heeding unsolicited paternal advice, he took a job with his father’s small travel business and soon launched his own company, the first steps toward becoming one of the most successful travel industry entrepreneurs in Boston.
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Mr. Lewis, who was chairman of the Grand Circle Corp. international travel conglomerate and chairman of Kensington Investment Co., died of an apparent cardiac event at his Kensington, N.H., home Wednesday. He was 74 and divided his time between Boston and Kensington, a small town that his maternal ancestors helped to settle in the 1600s.
With his wife, Harriet, Mr. Lewis was among Greater Boston’s most prolific and wide-ranging philanthropists. The couple and their foundations have given in excess of $250 million to more than 500 projects in 50 countries, according to the Lewis family.
Over the years, Lewis family donations also have helped fund local organizations and programs such as the West End House Boys & Girls Club and The Boston Foundation’s StreetSafe Boston initiative to reduce youth violence. The couple created a community advisory group to work with organizations including Artists for Humanity and Freedom House, according to The Boston Foundation.
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Nationally and internationally, their philanthropic contributions have helped programs at the Bears Ears National Monument in Utah, a bee project run by the Maijuna indigenous people in the Peruvian Amazon, and solar power initiatives in villages in India and Tanzania.
While building his first travel business, selling it, buying and building another travel company, and then launching a philanthropic life that didn’t fit established models, Mr. Lewis developed a philosophy that he was eager to share.
“Break the rules,” he said in an interview at the University of New Hampshire a couple of years ago that is posted on YouTube.
“Just keep breaking ‘em. Keep making mistakes,” he said, adding that “this world wants you in a box. The world is pushing you into a small box. Break the rules.”
Born in Boston on July 17, 1948, Alan Elliot Lewis was a son of Elizabeth Sawyer Lewis and Edward Lewis.
“My parents divorced when I was a young child, and I saw my father only on occasion,” Mr. Lewis wrote, “but each encounter left an indelible imprint.”
Along with running United Travel Service, a travel business that provided Alan’s entry-level initiation into the industry, Edward was a convicted bookmaker.
Mr. Lewis credited his father with teaching him to always help the underdog. And Mr. Lewis said his childhood — with its repeated changes of address — provided inadvertent preparation for his career in the adventure travel industry.
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“Every new place I had a fight because I was a new kid in the block, and that helped me get ready for my life,” he said of his youth in the UNH interview. “It was great for me because I got used to change. I got used to adapting to new places.”
Childhood also brought him to the place he considered his spiritual home. When he was 5, his mother began putting him on a bus in Boston to send him to visit his maternal grandmother, Ruth Sawyer, in Kensington.
In the late 1970s, Mr. Lewis and his wife bought land in Kensington from his great uncle. They expanded their holdings to 600 acres, which are now home to what is known as Alnoba, a retreat, leadership, and wellness facility.
“He always called it a sacred spiritual place,” said Martha Prybylo, executive vice president for social mission at Alnoba. “He walked that property any time of the day and felt a special responsibility to care for his ancestors’ land.”
While at Newton South High School, Mr. Lewis met Harriet Rothblatt. They dated briefly, and became a couple in their 20s.
“I was raised in a traditional New England family with my eyes set on college,” she wrote in “Driving With No Brakes,” which they coauthored. “Alan was a street-savvy kid with big dreams and a colorful past. You can see the attraction.”
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They married in 1972, the year before he cofounded Trans National Travel, and celebrated their 50th anniversary last month.
In the mid-1980s, they sold their interest in their travel agency, known as TNT, in order to travel more themselves and devote additional time to their two children.
Then Mr. Lewis heard that Grand Circle Travel was for sale. The company was losing $2 million a year when they bought it in 1985. The couple turned it into a business with more than $600 million in annual revenue and 35 offices around the world.
They founded Grand Circle Corp., which also includes two other travel businesses they acquired, and Kensington Investment to handle the family’s real estate and investment holdings, and its philanthropy.
Harriet chairs the Lewis Family Foundation. Their daughter, Charlotte of Marblehead, is Kensington’s chief operating officer. Their son, Edward of Park City, Utah, is Kensington’s chief executive officer.
Along with three grandchildren, Mr. Lewis also leaves a brother, Hank, with whom he has had well-publicized business disagreements that became court cases. In addition, Mr. Lewis leaves two half-siblings, Steven Rittenberg and Susan Lewis.
Burial will be private, and the family will sit shiva Monday through Friday beginning at 4 p.m. at Alnoba in Kensington.
“He made so much time to be in our lives, either physically or through phone calls or through letters or through e-mail,” Charlotte said of her father.
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“He really was such a loving man,” she said. “He was the biggest mentor, the biggest coach, the biggest supporter: ‘I’m always in your corner and I always have your back.’ ”
Mr. Lewis, she added, “had a serious code, and that was to tell the truth and chase after your dreams,” even when that meant pushing through challenging times.
“The last thing he said to me was, ‘Be comfortable being uncomfortable,’ and that’s how I want to live my life,” Charlotte said.
Particularly in his later years, Mr. Lewis became more reflective, writing in journals and sending “beautiful letters to his associates and friends,” Charlotte said.
Though Mr. Lewis “was a serious man, he also liked to have fun,” she said, and to the end he insisted others do as well.
Before Mr. Lewis died, he had planned to accompany his son to a beach for surfing, “but he was feeling tired and decided to lie down,” Charlotte said. “His last words to Edward were, ‘Go and have fun.’ ”
Bryan Marquard can be reached at bryan.marquard@globe.com.