Actress Amy Brenneman has traveled the world and has lived in Paris and Nepal, but she holds a special place in her heart for Martha’s Vineyard, where she and her husband, filmmaker Brad Silberling, have had a home for 25 years — first in Chilmark and then, for the past 15 years, in West Tisbury. In a phone call from her home there, which she described as an “incredible, soulful spread on the Tisbury Bay Pond,” Brenneman called the arts scene on the island “very special” and home to “some of the best artists and writers in the world.” Known for popular network TV shows like “Judging Amy,” which ran for six seasons (1999–2005), and was based on the real-life experiences of Brenneman’s mom, Frederica, a state superior court judge in Connecticut, and “Private Practice” (2007–13), Brenneman has also written plays — including the one that led to her most recent work, an autobiographical documentary called “Overcome.” Co-created with Sabrina Peck, it will be screened at the Woods Hole Film Festival, which kicks off on July 25. The film is about becoming an ally to and advocate for her daughter, who was born with a rare chromosomal abnormality. It examines the preconceptions of disability and what “normal” is, and the potential for and the challenges of achieving a fully inclusive society. Brenneman, 61, said the documentary is a recording of a 2024 live performance of “Overcome” at the Cotuit Center for the Arts. She said being the parent of a child or having a loved one who is different can be a “very isolating experience,” and she hopes the takeaway from her play and documentary is that “people are not alone” and that there are resources and a supportive community. Born in New London, Conn., and raised in Glastonbury, Conn., the Harvard University graduate splits her time between Los Angeles and the Vineyard. We caught up with Brenneman — who shares two children, Charlotte, 24, and Bodhi, 20, and two dogs, Mabel and Russell, with Silberling — to talk about all things travel.
If you could travel anywhere right now, where would you go? Right now? Probably Denmark. There is a hotel named Lovtag that is built in the trees that I look at on Instagram during stressful times. I love trees. And I visited Copenhagen briefly once, and I’ve always wanted to go back.
Do you prefer booking trips through a travel agent or on your own? I would say a combination. I am lucky to have had the same travel agent — Cindy Rogin at Mansour Travel Company in LA — for years and years. She knows where my stored miles are with airlines, etc. But the ideas always come from me, and often my ideas — Africa, Indonesia . . . — she may not have experience with, but through her network, finds amazing local travel agents for me to work with.
Thoughts on an “unplugged” vacation? Vital, and difficult these days. Too bad Wi-Fi is everywhere. I am politically engaged, so it’s a discipline for me to turn off my newsfeed, but it’s vital to refresh and gain perspective.
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What has been your worst vacation experience? The “worst” became one of the best last year in Cuba. I had traveled in developing countries in Asia and Africa, so I thought I was prepared — but Cuba is a communist country … very different. The first day, the Wi-Fi was tricky, the AC not consistent, and I had both kids with me. We don’t always need creature comforts, but honestly, I was a bit unprepared. But our guide was amazing, as are the Cuban people, and all of us left a week later quite transformed.
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What is your favorite childhood travel memory? Camping trips with my brothers and parents in Canada and Northern Maine. My parents were not adept campers, and often disasters would ensue. But days upon days in the station wagon, making up stories and songs with my brothers … trapped, but in the best way.
Do you vacation to relax, to learn, or for the adventure of it all? Adventure. I don’t go to relax — I’m a bit bored at the beach — and I crave getting into wild landscapes and cultures very different from my own. I love hiking, kayaking, and — OK, I’ll say it — glamping. I like to be in the wild but prefer to be pampered while doing so. Hiking in Sikkim in the Eastern Himalayas, safari in Kenya, horseback riding in Peru … and getting a good glass of wine at the end of the day!
What book do you plan on bringing with you to read on your next vacation? Poetry by Rumi and Mary Oliver.
If you could travel with one famous person/celebrity, who would it be? Gloria Steinem. Every encounter could be an opportunity for connection; every new place could be where a friendship could start.
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What is the best gift to give a traveler? A small, sturdy blank journal.
What is your go-to snack for a flight or a road trip? Almonds.
What is the coolest souvenir you’ve picked up on a vacation? A Bhutanese blanket from when I lived in Kathmandu. I can still smell the smoke and incense.
What is your favorite app/website for travel? I like looking at high-end websites – Abercrombie, Conde Nast, the Aman resorts … – then scaling it down. It gets me interested, then I start doing my own research.
What has travel taught you? Travel has taught me to shed the habits and persona that can develop at home. A new side of myself emerges — a new skill, or interest, or strength. I lived in Paris for six months when I was 17, then lived in Nepal for six months when I was 20. These long stretches changed me. I came back different. . . . I met people from around the world who stretched my viewpoint in ways previously unimaginable. We literally get to walk in another’s shoes, eat their food, breathe their air. It is humbling, in the best way.
What is your best travel tip? Stay flexible and let go.
Juliet Pennington can be reached at [email protected].