Oprah's 5 Most Iconic Vacations To Inspire Your Next Trip

How do you put together a travel bucket list if you're also one of the world's most influential people, with a global reach? Oprah Winfrey's lifelong itinerary of trips presents a case study in the conundrum of abundance. When the barriers of entry to travel — money, time, and logistics — are no longer issues, where do you go? Winfrey has become a model for the freewheeling, yet purposeful travel most avowed travellers can use to inspire their next trip. She's clocked so many miles on iconic vacations that she created a separate section of affordable travel finds for her Oprah's Favorite Things list in 2025.

From sunrise at the Grand Canyon to truffle hunting in Italy, Oprah's most iconic vacations share a common thread: a broader, stated purpose beyond chasing Instagram shots or pure curiosity (though there's plenty of that, too). It's travel as a syllabus for learning about the world and living briefly outside the limits of your comfort zone. It's a tall order to fill for a woman whose cultural gravitational force has its own name: The Oprah Effect. Whether she likes it or not, she changes the perception of a location simply by visiting it.

Yet all of this travel runs contrary to Winfrey's nature. "I don't think it's a secret to anyone who follows me that my idea of the perfect vacation is a staycation," she once wrote. "It's being able to sit under an oak tree with my dogs and read a really delicious book. When I do venture out, it has to be for a good reason." That set of priorities sets a high bar for planning, booking, and executing a trip. In other words, Oprah doesn't go out into the world — or do much else — half-heartedly. What better inspiration can you find?

While most of us settle for a weekend adventure or a half-decent week-long vacation, Oprah's travels can last a whole year. In 2017, Winfrey declared a "Year of Adventure" for her magazine, starting at the Grand Canyon. But more than a grand kickoff, Oprah's trip offered a second chance at a missed opportunity. The famous talk show host visited the Grand Canyon in 1993 but was so bogged down in the mechanics of filming her show that she didn't relish the experience. Her friend's 45-pound backpack resting heavily on her shoulders certainly didn't help. 

Her redo 24 years later offered a chance to rectify the missed opportunity, and it paid off. Winfrey was met with the sort of dramatic reveal that makes a trip worthwhile. She was met with a gorgeous sunrise, with a hawk floating overhead.

"My only plan was to be present," Oprah wrote of the experience, offering a valuable lesson in a world of hashtag-chasing travel. "The words 'amazing' and 'awesome' don't even come close to capturing what was in store: 'magnificent,' 'majestic,' 'sacred' are more like it. To watch the morning light illuminate the shadowed crevices of the canyon, as the sky turns a truly astonishing blue, is to witness one of the most miraculous wonders of the world. I took my time. I took it in. And I'll keep it with me forever."

Research suggests the human mind hates open loops. It's called the Zeigarnik Effect — that steady background hum and distraction created by unfinished business, looming heavy in your mental background. Oprah's recent hike to Telluride, Colorado, closed such a loop that had been bugging her since 1992. 

Back then, an admittedly out-of-shape Winfrey attempted the 4.5-mile Bear Creek Trail, a hike full of majestic scenery. She failed to reach the iconic waterfall at the end. In 2025, she took on the same trek — and finished it successfully.

"In 1992, I first visited Telluride and hiked the Bear Creek Trail," she wrote on social media. "I was 237 pounds — my highest weight ever. It took me half a day and felt impossible. I never even looked up and saw the view because I was only focused on one foot in front of the other and trying to breathe in the nearly 10,000-foot altitude. I didn't make it all the way to the waterfall. Today, I finished the trail in one hour and 48 minutes. I enjoyed every step, took in the beauty, and made it to the waterfall. Triumph!"

For most, stuffing your pantry means a trip to the local grocery store. For a favorite food, it may require a trip to a restaurant or specialty store. For Oprah, it looks like hopping aboard a flight to Italy to hunt for her universal food upgrade: truffles. "Its earthy, woody flavor makes almost everything taste better," Winfrey wrote on Oprah.com. "I literally don't leave home without it. When I travel, I have a jar, my assistant has a jar, security has a jar, and it's the one thing we request in a hotel: 'Can you make sure there's truffle salt in the room?'"

Winfrey discovered the coveted ingredient when Lisa Marie Presley included it in a gift basket in 2008. Her love of the underground fungus sent her to Umbria, Europe's most underrated summer holiday destination, in 2014. Their trip, coordinated with Sabatino, included an outing with truffle hunters and their dogs, digging up easier-to-find black truffles and their more delicate, pricier white siblings. She also gorged herself on a guilt-free truffle-everything: truffle pizza, truffle pasta, cured meats, and roasted chicken. Oprah ended the outing with 15 truffles, which she distributed among friends back home.

Never one for a small adventure, Winfrey decided to see all of America in one shot. Oprah and frequent travel companion Gayle King hopped into a red Chevrolet Impala and drove from Santa Barbara to New York City in 2006. (It was also prescient — her trip predated Chevy's recently revived "See the USA in your Chevrolet" ad campaign by two decades.) 

Along the way, the two encountered Oklahoma cowboys, played bingo, crashed a wedding or two, and made several friends. The trip was made all the more tense by Oprah's need to keep the stereo off while driving. "I learned a lot about myself," Oprah said in retrospect. During the home stretch of the trip, King's vision began to blur as the friends crossed the George Washington Bridge from New Jersey into Manhattan. "I learned I should drive alone," Winfrey deadpanned.

The trip ended with the duo pulling up to Times Square with enthusiastic crowds cheering while their photo was plastered on ABC's jumbotron. "I'm thinking I can't believe this thing is over," Winfrey said years later in an interview about the trip. "And there's a little bit of excitement about it. But really, Gayle says, 'Oh, gee, I had a good time.' It was wonderful in the category of experience, and to know not to do it that way ever again. That's why it was beneficial to me." Oprah gave away the Impala — of course — after it had made the cross-country trip. And the two recreated the road trip, at least partially, 15 years later.

Where would you expect to find a deeply intellectual woman, an admitted homebody and bookworm with one of the world's most influential book clubs? Probably the largest independent bookstore in the world, right? Wrong. You might, however, have found her in the Blue Marin club in Ibiza in 2015. The then 61-year-old tossed back tequila shots with the likes of famed record producer Jimmy Iovine. (The Queen of Talk loved her tequila, admitting to once tossing back 17 shots in a single night). Winfrey was joined by Gayle King (of course) and crossed paths with Will.i.am and Disney's head honcho, Bob Iger.

"They say it's better in Ibiza," King wrote in an Instagram post about the outing. "Take in teeny pink hats, umm ... limber dancers and Oprah leads Jimmy Iovine in tequila shots! Good times good friends." The resulting blurry nighttime collage of shots includes Oprah holding a literal fan, scantily clad dancers, and yes, her knocking back shots. It's the sort of inspired, fish-out-of-water jaunt one should absolutely make if youth and vitality need a boost. (Independent book shops aren't too bad, though, either; Winfrey did host a virtual event in Powell's Books back in 2021.)

Choosing a top five for a dedicated (and deep-pocketed) world traveler like Oprah Winfrey presents a unique challenge. What to leave out? Her passport has been heavily stamped, both for work and pleasure. There was the 2010 camping trip in Yosemite, which included an up-close look at the park's famous Giant Grizzly sequoia tree. Some filters needed to be set.

First, the trip needed to go beyond the usual global galavanting. Jaunts like Winfrey's 2018 trip to Dubrovnik, Croatia, fell out of contention. The destination, one of Europe's most walkable cities and a living fairytale, has become a magnet for A-listers. There's also the team-building, business-adjacent outings that Winfrey does to show her staff and inner circle some appreciation. That knocked her recent trip to Maui off the list.

The North Star for the list became the word "inspire." The outing had to be inspired by an ongoing narrative in Winfrey's personal journey and also lead to a basic human truth. Hence, taking care of unfinished business in Telluride automatically moved to the top of the list. The cross-country drive with King provided a case study in the value of friendship, even if that friend can sometimes be a walking hassle. The rest of the trips share a similar inspiring narrative and accessibility.