The Trips That Transformed Oprah, Gayle, and Our Favorite Travel Muses

We recently asked our Oprah Daily community what their greatest act of self-care would be if time and resources weren’t a barrier. All responses resoundingly—and unequivocally—involved some form of travel. But beyond the usual bucket-list suspects (African safari, Taj Mahal, the Galápagos), we were pleasantly surprised by the overwhelming desire for experiences that facilitate personal transformation: the kinds of mind-expanding, soul-feeding, relationship-deepening journeys—both solo and with loved ones—that remind them of what really matters. We heard a lot about the desire to do walking trips as a way to connect with nature and invite a spiritual awakening; the urge to retrace one’s ancestry, however painful the journey, in some cases; and a growing sense of urgency to gather friends, children, and grandchildren in one place, even if only for a few days. We understood that in a moment of intense polarization around the globe, so many of us yearn for experiences that remind us of our shared humanity. As Maya Angelou once said, “Perhaps travel cannot prevent bigotry, but by demonstrating that all people cry, laugh, eat, worry, and die, it can introduce the idea that if we try and understand each other, we may even become friends.”

If you’ve been following along with Oprah these past few years, you’ve likely been living vicariously through her travels around the world. But even beyond the dreamy destinations—from her cradle-of-civilization pilgrimage to Petra to her first visit to Japan to see the cherry blossoms to her girls’ spa week in Italy—what strikes us most about these trips isn’t so much the where (although each voyage is more dazzling than the last) or even the how, so much as the with whom. And, of course, the why. “Because life is better when you share it, I believe,” says Oprah. As we’ve witnessed, when the world reopened post-pandemic, she was ready to be in it again, but pretty much only if she could be with a handful of her besties.

Because for those of us like Oprah who love adventure as much as we love the homes and people we get to return to, the stakes for a good trip are even higher. “My forever life mantra is aligned with Dorothy’s from The Wizard of Oz: ‘There’s no place like home.’ I have purposely created beautiful spaces because I’m, at heart, a homebody,” Oprah says. “So when I do venture beyond my own backyard, I like traveling with a purpose.” For her, and so many of us who are always on the go, the perennial question is: What is worth the time, energy, and expense of leaving the hard-won sanctuary of one’s own home? Even though travel is by definition a luxury, it also comes with the pressure to narrow the universe of possibilities and choose that one perfect trip guaranteed to make memories, create a much-needed shift in perspective, and maybe even change our lives.

For guidance, we turn to some of our favorite in-the-know friends, contributors, and travel muses—people whose pivotal travel memories inspire us to identify what really makes us tick and to stretch beyond our comfort zones, and whose recommendations we squirrel away for when we are ready. For us, beyond the magic of the locales, travel is all about the ways in which our eyes, ears, and souls get imprinted forever after, and turn into stories that we’ll tell for years to come. “I love to combine work and play, so whenever I’m invited to speak across the globe, I book a few days before so I can explore, meet people, and enjoy whatever food they’re offering,” Oprah says. “And then I incorporate those encounters or anecdotes into my conversations. —Pilar Guzmán, editoral director, Oprah Daily

Gayle King, editor at large, Oprah Daily

“In early 2000, I got to see the big five (lion, rhino, buffalo, leopard, elephant) in South Africa and all the other smaller animals (hyenas, gazelles, impalas) roaming free in their own habitat. I never felt the same about going to the zoo! It suddenly seemed cruel and inhumane to keep these majestic animals locked up in cages just so we could gawk. It changed my relationship to animals forever after.”

Yolanda Edwards, founder, Yolo Journal

“We were invited last-minute to join friends traveling on the Nile with Nour el Nil—a fleet of traditional dahabiyas that strike just the right balance of bohemian luxury and cultural immersion as they make their way from Luxor to Aswan. There was this one moment when we were led through the village of Aswan when the guide encouraged us not to stop as locals swarmed us. I have often struggled with the discomfort of steeling myself—and become momentarily hardened—when faced with so much poverty and need. While most of the crowd had fallen off as we made our way to the desert, a few kids kept following us. One young boy, who was 5 years old and accompanied by his 3-year-old brother, asked my name. I asked for theirs in return. They giggled and beamed at me with the sweetest smiles you can imagine. As we left town and walked through the sand dunes, the kids kept following us, scaling the high rocks and calling my name from ever-greater distances. At one point, they appeared atop a super-high rock across the desert, and the boys raised their hands and yelled, “Yolaaaanda!” I had tears in my eyes and called back to them, our voices echoing in tandem across the lunar landscape. I felt seen—and saw—in a way that other sorts of prescriptive bucket-list travel and our busy, busy lives don’t allow for. I realized in that moment just how desensitized I’d become despite myself. Of all the travel I do for a living, this was a personal highlight. I was so happy that I let down my guard and was able to experience the purity of human connection across cultural and linguistic barriers.”

Sheila Bridges, principal, Sheila Bridges Design

“I first went to Iceland with a group of friends for my 50th. For me, it was instantly transformative. There was something about the country that kept calling me back. So much so that the following year, I ended up buying a home there. It’s definitely not for everyone—though it’s much easier to get there than people realize and an easy stopover on my frequent trips to Europe. As a creative person, so much of it had to do with the light. The landscape, nature, and people that never stop feeding my curiosity. And the horses. The geothermal waters are truly healing. It’s the place where I feel instant escape. My true happy place.”

Athena Calderone, designer, author, and founder, EyeSwoon

“The first time we visited the Aeolian Islands as a family in 2014 completely shifted how we saw the world and engaged with one another. My husband, Victor, is Sicilian, so first and foremost, it was incredible to be in the motherland for 10 days together. I can just remember how everything slowed down. It tends to do that in Italy anyway, but in the remote Aeolian Islands, it truly feels like a different world. Being so far removed from reality and our day-to-day routines made us connect more, laugh more, adventure more, dream more, and open our hearts up more. [Our son] Jivan was at such a pivotal age. I can distinctly remember Victor speaking in his native Sicilian dialect on the island of Salina and witnessing the pure joy and awe on Jivan’s face at seeing this different version of his dad.

Each day, we would rent a small boat from a Sicilian local, hop in, and set off for hours, sometimes all day. No captain here, just the three of us on adventures across the deep-blue crystalline sea, visiting different islands. I can still hear the laughter and feel the joy as we sped across the expansive sea with the salty water spraying Jivan’s small body as he sat at the front of the boat, his long hair tousled. I will never forget steering into this cove with big black lava stones and diving into the deep turquoise water, or the time we approached the island of Stromboli and watched the smoke from the active volcano. I vividly recall Jivan’s excitement at seeing the rich black sand, the lava stone, and just the transparent magnitude of his surroundings that felt so far removed from his life in the city.

When we weren’t on the water, we were whipping around the winding roads on a moped, inhaling the salt air and soaking up the red sky as the sun slid into the sea. Afterward, we’d sit together on the back deck overlooking Stromboli for dinner, exhausted and exhilarated, as we recounted the day’s events with such enthusiasm. We played ‘I spy with my little eye’ (usually spying lemon or fig trees or cacti), and everything felt so perfect, so present, so precious. I remember wanting to bottle up the purity of the moment! There was such a deep level of connection. There’s nothing like being on an adventure in a place that forces you to slow down and allows you to connect with your family more. It really puts everything into perspective.”

Adam Glassman, creative director, Oprah Daily

“When I do go on vacation, I like to go in with a sense of purpose. After hearing about it for years, I finally went to the famous Vivamayr in Austria, a luxury medical detox and wellness resort that focuses on prevention and is set in the most gorgeous part of the Austrian Alps. Detoxification is at the heart of this program, with a big emphasis on rest and a cleansing of the digestive system. The philosophy being that health and the immune system originate in the gut and that the combination of detoxifying treatments, the reduction of inflammation, and holistic therapies can help reset it. I got a big reeducation on exercise and eating habits—I was encouraged, for example, to chew my food 40 to 60 times per bite to ensure proper digestion, even when eating soup (!) and learned about all the ways in which digestion impacts everything from weight and circulation to skin and headaches. But after a week of truly unplugging, hiking in the mountains in between treatments, the greatest takeaway was the importance of rest.

Each guest is assigned to a doctor and gets thorough diagnostics and an individualized program, which includes medical appointments, IV drips, foot baths, mud wraps, nasal reflexology, Watsu water therapy, Pilates, myofascial therapy, breathwork, osteopathy, salt scrubs, cryotherapy, sessions with oxygen tanks, and flushing of the liver and stomach with Epsom salts—all of which are designed to help release energy blockages and emotional buildups.

Ultimately the program purges the body of toxins, and as the week went on, I felt euphoric. By the end, I left feeling rested and full of energy—and with real learnings to take back to the real world. Both a physical and emotional detox, my time there was life-changing. It reminded me of the importance of taking care of myself, giving myself permission to rest and take an actual vacation a few times a year, to enjoy life, and to do the kind of exercise that is actually fun (walking with friends outdoors), not punishing.”

David Prior, cofounder and CEO, Prior

“Syria was the place to travel. It was where the souks were still real, and riads were mixing more modern design with a patina of history and cool Syrian style. Damascus was supposed to be the ‘next Marrakech.’ Levantine food was having a moment with the flavors of fragrant rosewater, piquant sumac, and sweet pomegranate molasses in our kitchens (thanks, Ottolenghi!). The history and majesty of Damascus felt matched only by Rome, and with its dense, exquisite beauty, Aleppo was like Florence. The Axis of Evil was a thing of the past now. Then, suddenly, it was not. I traveled to Syria not as a war-zone correspondent but as a travel writer covering the next exciting cosmopolitan travel destination right before the civil war broke out. In the years since, Aleppo has been destroyed and Damascus emptied of the friends I made. Now when I look at the destruction of conflict anywhere around the world, I think about our shared cultural richness that is gone forever and of the people whose lives made those exquisite buildings, bold food, and moving traditions come to life. It gave a face and place to war, and it is a lesson that is hard to forget.”

Bevy Smith, author, TV/radio host, and actress

“Every trip I ever take transforms me in one way or another. But when I think back to the one that solidified a change in my life’s work, it was when I did my sepia version of Eat Pray Love after quitting my job at Rolling Stone in February 2005. First stop was South Africa. I was traveling alone as a single Black woman. It seemed like an easy entry point since it’s English-speaking and pretty Westernized. While incredibly beautiful, Cape Town was much more European than I expected. I expected to see many more Black people in the center of things rather than in the townships. Johannesburg, on the other hand, was more like Atlanta—like Black suburbia, where Black people were doing well. There is a middle class and an upper class, but still not Africa as I’d imagined it. My parents grew up in Jim Crow South. Even post-apartheid, South Africa felt like Jim Crow South to me. It doesn’t matter if you are the president of a bank; it’s still segregated. This was the political part of my trip, and I was searching for freedom and for a vision for my life to gel. I went on to the nature part of the trip, to Zambia and Victoria Falls, which was great, but then I came home for a week and went to Brazil—and that’s when the journey really began. I’ve never felt so firmly connected to my African roots as I did in Salvador de Bahia, which has the largest African population outside Africa.

Culturally, they have retained so much of their Africanness, which really resonated and was so transformational for me. My experience in Bahia inspired me and gave me permission to lead with the culture at all times, which I fight tooth and nail for. I show up on TV as a Black woman on GMA and BET and bring this sense of culture to my dinner-party business—like the one I’m doing in Brasília in 2025 in the middle of all these important buildings by Niemeyer, which will look like a scene from Gattaca. For me, travel is about tracing my cultural roots. It’s a grounding. It’s in the soil of a place. Like when I went to the Cape of Good Hope, I felt the slave history. I felt the intensity of the transatlantic slave trade when I went to Ghana in 2019, the year of the return and a reckoning of sorts. I usually go places where there is a slavery connection. I did a walking tour with African Lisbon, which gives the history of the slave trade in Lisbon. It shows up in so many ways. Even in beautiful Amsterdam, “Black Peter”—a Moorish servant who accompanies Saint Nicholas at Christmastime—shows up in blackface in department stores. Like, what the fuck is this? I’m a global traveler, and there are always traces of Black bodies being seen as a commodity around the world. There is always that connective tissue you can’t forget.”

Pia Baroncini, founder, LPA and Baroncini Import & Co.

“We have an unusual living situation, by American standards anyway, in that our little family of three—my husband, my daughter, Carmela, and I—moved in with my mother right after my father died. We were at my parents’ house on Sunday night for dinner when my father dropped dead. It was shortly thereafter that we made the decision to buy the house and have my mother live with us. And it all really works. My husband and mother get along. We both get to have a mom who sort of takes care of us as we build our business, and my daughter gets her grandmother all the time.

But it wasn’t until we all went to Sicily together, where my husband is from, that my mother really fully understood him—and Italian culture. I think people don’t really know the real Italy, what it’s like to live there, outside the tourist cities. It is the number one place people romanticize, but real neighborhoods can be very tricky. I’d been there a couple of times before and I’d seen the underbelly and day-to-day life, which made me understand how my husband operates on a core level. When his mom was dying, we went back to be with her. I remember when we started dating, there were things that bothered Davide, where he felt very misunderstood by Americans.

I had been there before with just him; it’s where we got engaged. But this time, when the three of us got to see him there for the first time all together and meet his family, I realized my mother was able to contextualize him. I watched her observe him in his environment and how he is with his family and friends, how affectionate he is with his barber, his priest, his postman. There were things before this trip she used to bristle at, like why he didn’t want her to walk across the street by herself—in his small town, women don’t do things like that, and he sees it as his duty to protect her. Whereas in the U.S., she would react to that feeling of being controlled, here it made sense, and she leaned into it. And even though he was the one whose arms she cried in when my dad died, she didn’t fully get him and things like why he was so bothered when she would eat lunch standing up. When she saw where he came from and the rituals around food, which isn’t taken for granted in the poorer parts of Sicily where he’s from, she understood the respect around meals—respect that you actually have a meal to eat—and why they always lay a tablecloth.

I realized it was the first time I’ve seen her being really quiet. She loves to tell a story. But in Sicily she was in observation mode, experiencing him in his natural habitat of amazing family and friends and appreciating the way he treats people. Multiple times on the trip, she would spontaneously go over to hug and kiss him. She would say things like, ‘I’m so happy you are the father of my granddaughter.’ It was really life-changing and cemented our bond as a family unit.”

Nate Berkus, interior designer and author

“Every trip has changed me in some way, but perhaps the most impactful was a two-week trip through the central highlands of Mexico, in a rented car and with one small carry-on. I went from the beach to the mountains, from a tree house to the Hacienda de San Antonio, and will always remember the family in the elevator with me at Sanborns in Morelia. It was the only building with an elevator, and the family was nervous. It reset something for me.”

Andrea Gentl, photographer

“The first time I left home was to study in Italy when I was 20 years old. Until then, I had only traveled on a plane to Southern California with a high school friend. I landed in Rome bleary-eyed and hungry. In the Roma Termini en route to Siena that cold January morning, I ate the first of many train station sandwiches I would eat over the course of a lifetime. In fact, I ate two. Neither was better than the other; they were pretty standard but satisfied my hunger the same way eating anything after a long swim does. I was deeply sated but also remember feeling a little wave of sadness, having nothing to do with the actual quality of the sandwich. One was made of paper-thin mortadella with slightly thicker pieces of provolone wedged between two salty pieces of focaccia, the crust soaked in olive oil. The other was a simple frittata tucked between the same salty focaccia. I’ve known from early on that Italy changed me in many ways, but it was those first humble train station sandwiches that set me on a course of searching for both familiar and new flavors. It wasn’t their unfamiliarity that jolted me that morning; it was their utter familiarity, as though I had accessed the very smell and taste of my deepest memories—a taste that immediately made me feel that twinge of melancholy.

In that moment, I thought about my grandfather, the youngest of his siblings. He was born in New York City, while his brothers were born in Rome. My grandfather loved paper-thin mortadella about as much as he loved provolone. When I was a kid, I used to ask him to tell me about his childhood. He mostly waved me off with a laugh, but once, he told me about a cheese shop called Alleva that he walked to as a boy from his family’s railroad flat on Second Avenue to pick up cheese. He was 6 or 7 at the time. Little did I know then that I would move just a scant few blocks from this shop some 20 years later. I was so excited when I saw it and called him immediately. The shop that he went to was still right there on Grand Street—that is, until it lost its lease last year after 130 years. Large rounds of provolone bound in waxed rope hung in the window, much like, I imagine, when he was a boy. The cheesemaker’s name, a deep red, bled into the surface of the cheese. I thought about those large rounds making the journey from Italy to New York, much like my family had. I sometimes stop and imagine my grandfather walking up that street as a boy. I would give anything to see him there, just once. I think about him often and wonder if I sometimes walk the same paths as he did. Do I step in his small footsteps from almost a century ago? When I bit into those sandwiches that first morning in Rome, I felt closer and farther away from home than ever. I now understand that what I felt that day was an ancestral food memory. Memory drives much of my curiosity and curation of food. That first trip to Italy opened a portal for me. I became a traveler. As a photographer, many of my photographs start with a memory, a taste, a smell, or a feeling. Memory is what I try to get at as a photographer, and it’s what I access when I cook; it’s when a thousand tiny pieces come together to make something new.”

Paula Froelich, senior story editor and entertainment correspondent, NewsNation

“It was 2017 and kind of a bad year. I wasn’t really working, and I had quit smoking, which added even more stress. I got an offer to go on a Walk Japan trip along the Kumano Kodo trail, which I knew nothing about. I just wanted to escape my life for a minute. I’d never really hiked, and I’d smoked for decades, and here I was having to hike for sometimes six hours at a time. The trip ticked every box: physical activity—I didn’t know how strenuous it would be—and also intellectual and aesthetic stimulation. It was stunningly beautiful. It also got me to a spiritual place, thinking of dead relatives (‘Thank you, Grandma!’) in a land that reveres ancestors and history as it relates to mortality. I came home with a clear mindset and was mentally and physically stronger than I’ve ever felt. I think of it every day. If I have a hard day, I go back to it. I do the walk in my mind. One foot in front of the other. It was a lesson in slow living and a constant reminder that I can do hard things and that my lungs actually work. I rebuilt them and myself on that trip.”

J.J. Martin, founder, La DoubleJ

“I’m no longer interested in being a tourist when I travel. I want a really deep and connective experience. Going to Egypt was something I’d been thinking about for many years, and I purposefully waited until I could find someone to help me take a deep dive into the spiritual aspects of the land. I went for the first time three years ago, led by a high priestess named Dee Kennedy, who not only introduced me to the Ancient Egyptian Mystery School as a wisdom tradition but also guided me through an initiation process in each of the temples we visited. It was so deep and powerful that halfway through the trip, I felt like I was taking psychedelics. All the meditations, rituals, and energy activations we did in these sacred sites brought forth these incredible spontaneous altered states. I’d never imagined traveling to a place and being so connected to the land. I came back transformed on a physical, mental, emotional, spiritual, and energetic level. I now go back every year and cohost these initiation journeys with Dee. The next one is coming up this fall, from October 18 to 31 (sign up here once the trip goes live: sacredegypt.com/sacredscribes).”

Jill Kargman, author and actress

“My skiing-addicted husband booked a family trip to the middle of nowhere. Nestled on the Austria-Italy border, tucked between two mountains worthy of The Lord of the Rings or The Sound of Music, depending on the season, Forestis was my dream family ski/spa hotel. The five of us marveled immediately at the sleek James Bond–villain-esque vibes juxtaposed with the old-school local signage, the German black-letter fonts creeping us out a little, as we wound our way up the hilly pass. The rooms seem hella spartan at first, but then you realize it’s meant to make the actual star—the view—shine brighter. The enormous floor-to-ceiling windows are perched atop the most insane panorama of snow-capped ranges I’ve ever woken up to. It’s almost too breathtaking to look at, and it never gets old. The massages and facials were next-level heavenly, with treatment rooms all smashed into the mountain and heated tables overlooking the blizzard outside. I have truly never felt more unplugged or pummeled to perfection. Forget a sandy beach; Forestis was my personal slice of paradise.”

You Might Also Like