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 Hummel and Jill Hummel ’81
On their 38th wedding anniversary, Jill Hummel ÌÇÐÄ´«Ã½™81 and her husband, ZackÌÇÐÄ´«Ã½”otherwise known by their self-appointed titles of Captain Zack and Admiral JillÌÇÐÄ´«Ã½”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 ÌÇÐÄ´«Ã½œtotally awesomeÌÇÐÄ´«Ã½� in Italian slangÌÇÐÄ´«Ã½”an apt description for this exciting new phase of their lives.
Today, the coupleÌÇÐÄ´«Ã½™s address is wherever the wind takes them. So far, thatÌÇÐÄ´«Ã½™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. ÌÇÐÄ´«Ã½œWe love adventure, learning, and taking on a challenge,ÌÇÐÄ´«Ã½� says Jill. ÌÇÐÄ´«Ã½œSailing 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, theyÌÇÐÄ´«Ã½™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, ÌÇÐÄ´«Ã½œIf not now, when?ÌÇÐÄ´«Ã½� ThatÌÇÐÄ´«Ã½™s when their daydreams started turning into real plansÌÇÐÄ´«Ã½”they prepared their lives, plotted their routes, and got a bigger boat.
And off they went. ÌÇÐÄ´«Ã½œWe love this life,ÌÇÐÄ´«Ã½� Jill says. ÌÇÐÄ´«Ã½œBy no means is it easy, thoughÌÇÐÄ´«Ã½”it requires careful planning, constant vigilance, and tireless maintenance.ÌÇÐÄ´«Ã½� The couple wouldnÌÇÐÄ´«Ã½™t have it any other way. ÌÇÐÄ´«Ã½œWe get through challenges every dayÌÇÐÄ´«Ã½”thatÌÇÐÄ´«Ã½™s just the way of life on a boat,ÌÇÐÄ´«Ã½� adds Zack. ÌÇÐÄ´«Ã½œWe also have a lot of joy in our lives and appreciate everything more, from sunsets to snorkeling to each other.ÌÇÐÄ´«Ã½�
We love adventure, learning, and taking on a challenge,ÌÇÐÄ´«Ã½� says Jill. ÌÇÐÄ´«Ã½œSailing brings it all together for us.

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. ÌÇÐÄ´«Ã½œIt was an incredible personal interactionÌÇÐÄ´«Ã½”kind of like a playdateÌÇÐÄ´«Ã½”with these dolphins,ÌÇÐÄ´«Ã½� Zack says.

The Boat:
Home is on the HummelÌÇÐÄ´«Ã½™s semi-custom Hylas sailboat. ÌÇÐÄ´«Ã½œWe love everything about itÌÇÐÄ´«Ã½”from its solid build and hull shape to the headroom and beautiful woodwork,ÌÇÐÄ´«Ã½� says Zack. The primary cabin is located aft, featuring a king- size bed, an ensuite head, and a stall shower. The forward, or ÌÇÐÄ´«Ã½œVIP,ÌÇÐÄ´«Ã½� cabin has a private entrance and a second head, while the third cabin is used to store tools, scuba equipment, and other gear.

Always a Yellowjacket:
Jill and Zack have made a custom sail as well as hats, inspired by their last name, Hummel, which means ÌÇÐÄ´«Ã½œbumblebeeÌÇÐÄ´«Ã½� in German.

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 theyÌÇÐÄ´«Ã½™re wearing a life jacket. For the Hummels and other sailing couples, the term ÌÇÐÄ´«Ã½œpartnerÌÇÐÄ´«Ã½� carries a profound significance when it comes to ensuring each otherÌÇÐÄ´«Ã½™s safety.

Keeping the Peace :
Effective communication is essential to successfully living with your spouse 24/7 in a small space, Jill says. ÌÇÐÄ´«Ã½œCruising couples discuss this topic frequently. ItÌÇÐÄ´«Ã½™s crucial to talk about what brings you happiness and what bothers youÌÇÐÄ´«Ã½”on a boat, thereÌÇÐÄ´«Ã½™s no space for significant unresolved issues.ÌÇÐÄ´«Ã½� Jill and Zack encountered another cruising couple in Antigua who named their dinghy ÌÇÐÄ´«Ã½œTime Out.ÌÇÐÄ´«Ã½� Whenever one of them needs a break, they use it.

Idyllic Moments:
The couple agreesÌÇÐÄ´«Ã½”the most restful and peaceful times come when they are way out on the deep ocean, especially at night, when thereÌÇÐÄ´«Ã½™s no land in sight, no light, and no noise pollution. ÌÇÐÄ´«Ã½œThere also arenÌÇÐÄ´«Ã½™t any sharp, pointy things in the water that could harm the boat,ÌÇÐÄ´«Ã½� adds Zack. Another plus: The sky is vast, and the stars are incredible.
Learn more
- Follow the Hummels at
- Where in the world is the CheFigata? real-time location
- Got the travel bug? Find an adventure through the UniversityÌÇÐÄ´«Ã½™s Travel Club
- Explore Lifelong Learning opportunities with the University
This story also appears in the summer 2023 issue of Buzz magazine.
ÌÇÐÄ´«Ã½” Kristine Kappel Thompson, June 2023


