The adventures of Zack and Jill

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 and jill stand on a boat with sunset and rock formation seen behind them

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.”

We love adventure, learning, and taking on a challenge,” says Jill. “Sailing brings it all together for us.
Dolphins in water against a sailboat

The Wildlife:

In Turks and Caicos, Zack jumped into the water for a swim and was soon joined by two dolphins. Jill took notice, and the couple ended up taking turns in the water, each spending one-on-one time with the smaller dolphin while the other looked on. “It was an incredible personal interaction—kind of like a playdate—with these dolphins,” Zack says.

sailboat on water in front of a cloudy sky

The Boat:

Home is on the Hummel’s semi-custom Hylas sailboat. “We love everything about it—from its solid build and hull shape to the headroom and beautiful woodwork,” says Zack. The primary cabin is located aft, featuring a king- size bed, an ensuite head, and a stall shower. The forward, or “VIP,” cabin has a private entrance and a second head, while the third cabin is used to store tools, scuba equipment, and other gear.

sailboat sail with yellow jacket design

Always a Yellowjacket:

Jill and Zack have made a custom sail as well as hats, inspired by their last name, Hummel, which means “bumblebee” in German.

Jill seen holding a rope, looking upwards while on a boat

Safety First:

Zack and Jill follow strict safety protocols. For instance, while on passage, one person is always assigned to keep watch and helm the ship. The designated person cannot leave the cockpit unless the other partner is awake and present nearby. Zack says they have heard too many tragic stories of people getting tangled up in lines and dragged into the water, even if they’re wearing a life jacket. For the Hummels and other sailing couples, the term “partner” carries a profound significance when it comes to ensuring each other’s safety.

Zack and Jill hold a sign that says "Che Figata"

Keeping the Peace :

Effective communication is essential to successfully living with your spouse 24/7 in a small space, Jill says. “Cruising couples discuss this topic frequently. It’s crucial to talk about what brings you happiness and what bothers you—on a boat, there’s no space for significant unresolved issues.” Jill and Zack encountered another cruising couple in Antigua who named their dinghy “Time Out.” Whenever one of them needs a break, they use it.

sunset over the water

Idyllic Moments:

The couple agrees—the most restful and peaceful times come when they are way out on the deep ocean, especially at night, when there’s no land in sight, no light, and no noise pollution. “There also aren’t any sharp, pointy things in the water that could harm the boat,” adds Zack. Another plus: The sky is vast, and the stars are incredible.

Learn more

This story also appears in the summer 2023 issue of Buzz magazine.

— Kristine Kappel Thompson, June 2023