Stories from Real Virtuoso Travelers Why I Travel: Judith Hennessey

Why I Travel: Judith Hennessey

The Hennesseys at the Grand Canyon.
The Hennesseys at the Grand Canyon.

Judith Hennessey doesn’t do anything small. For years, the Saint Louis native and raconteur ran her family’s auto dealership, one of the largest in the country. When a craving for elbow room lured her from the city, she and her husband, Timothy, bought a Missouri farmhouse on 50 acres. On the side, Hennessey penned and sold First Rodeo, a novel, which she then adapted into a screenplay (she’s since finished its sequel and started a third novel). Whether she’s tracing family roots in Italy, decompressing in the desert, or seeking farm-fresh good­ness in Tennessee, Hennessey relies on her Virtuoso travel advisor to handle her outsize travel plans.
I travel because it teaches me about who I am. Sometimes you need to get a little lost to find yourself. Also, I just like talking to people.
Travel incentives were a big part of sales at DiSalvo Jeep/ Chrysler. My father traveled all over the world, and I got to join him on a few exotic trips. Those incentive trips were always first-class plus – it’s probably where I got a taste for the Virtuoso travel style.
My father’s parents came to Saint Louis from Sicily, and those roots run deep. I told my advisor we wanted to find our family, and she reached out to a local contact to help make arrange­ments. I’d heard you have to go to these tiny villages and wait in line all day at city hall, but I said, “Nope. I don’t do that.” She arranged everything in advance. Our guide picked us up in a white minivan and took us to our ancestral village of Siculiana, where we waited for things to unfold.

Judith Hennessey (left) with her son and sister in Sicily.
Judith Hennessey (left) with her son and sister in Sicily.
The town is on top of a hill with a castle, and the second we pull in, people start showing up. This one’s the mayor. That one’s the building commissioner. They’re all dressed in suits; I’m in yoga pants, but they treat us like important people. Everyone’s waving their hands. They’re call­ing us DiSalvo and Marino, our grandparents’ names. My sister spots two ladies – one brunette, one strawberry blonde – and goes, “Hey, Judy, they look like us!” Turns out they’re our long-lost cousins. A little old farmer in his Sunday best starts crying, which gets me crying.
My advisor knows I’m a picky traveler. My husband snores; I need a suite with an actual door and another bed in case I need to kick him out of the room.
I’m a bathtub girl, so soaking tubs are very important. So are views. When you can com­bine the two – like at Amangiri in Utah, the most beautiful hotel in the world – even bet­ter. It’s far from everything, but my advisor reminds me that paradise is never easy to get to.
Great Smoky Mountains hideaway, Blackberry Farm.
Great Smoky Mountains hideaway, Blackberry Farm.
Photo by Beall + Thomas Photography

Blackberry Farm near Knoxville, Tennes­see, is one of my happy places. People talk about farm-to-table, but these people hang and dry their own prosciutto, they make their own cheese, they brew their own beer. It’s table on the farm!
I get along way better with my husband when we travel. At home, he’s working, and we don’t have time to focus on each other – it’s a bummer. Isn’t that originally why people vacationed? To spend quality time together?
My travel dreams list is straight A’s: I haven’t been to Alaska. I’m dying to go to Antarctica. I want to see polar bears in the Arctic. And I need to get to Africa.

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