The adventures of Zack and Jill

An alumna and her husband retired, sold everything, and now live full-time on their 56-foot sailboat

Zack Hummel and Jill Hummel ’81

On their 38th wedding anniversary, Jill Hummel ’81 and her husband, Zack—otherwise known by their self-appointed titles of Captain Zack and Admiral Jill—moved out of their three-story home in Connecticut and onto their 500-square-foot sailboat. It was August 1, 2020, and the couple decided to brand their new home Che Figata, which means “totally awesome” in Italian slang—an apt description for this exciting new phase of their lives.

Today, the couple’s address is wherever the wind takes them. So far, that’s included the entire east coast of the United States, the Caribbean Islands, and even the Galapagos. Their ultimate plan is to circumnavigate the world over the next few years. “We love adventure, learning, and taking on a challenge,” says Jill. “Sailing brings it all together for us.”

This spring and early summer, the Hummels are sailing to Australia and New Zealand with about 30 other boats affiliated with the World Sailing Club. When they get to Australia, they plan to rent an RV and explore by land for about six months before charting a course to Indonesia and Thailand.

Fate, the Hummels say, brought the two of them together. Forty-three years ago, they were college students participating in the same Semester in Politics program in London. Jill hailed from the University of Rochester, and Zack from the University of Michigan. They hit it off, returned home, and maintained a long-distance relationship before marrying in 1982.

Since then, they’ve both earned law degrees, raised three children together, and welcomed two grandkids. They also pursued busy, high-profile careers. Most recently, Jill served as the president of Anthem Blue Cross Blue Shield in Connecticut, and Zack was a partner at the Shipman & Goodwin law firm working out of the Stamford, Connecticut, office.

The couple’s love for sailing started 16 years ago when they bought their first sailboat. Zack, who grew up sailing on Lake Michigan, introduced Jill to the sport. After years of sailing together, they started talking about the possibility of selling everything and living on a boat. A few years ago, the Hummels said, “If not now, when?” That’s when their daydreams started turning into real plans—they prepared their lives, plotted their routes, and got a bigger boat.

And off they went. “We love this life,” Jill says. “By no means is it easy, though—it requires careful planning, constant vigilance, and tireless maintenance.” The couple wouldn’t have it any other way. “We get through challenges every day—that’s just the way of life on a boat,” adds Zack. “We also have a lot of joy in our lives and appreciate everything more, from sunsets to snorkeling to each other.”