Catherine Heald ‘80: Guiding Travel Adventures Throughout the Globe

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Catherine Heald ‘80: Guiding Travel Adventures Throughout the Globe

Catherine Heald was working on Wall Street at LF Rothschild when she completely upended her life to move to Hong Kong, sight unseen. With her life savings of $1,000 in hand and the phone numbers of two contacts in her pocket, she boarded a plane, having absolutely no idea what she would do when she landed.

To her family, the decision to abandon her career in the financial/ technology industry was impulsive and totally impractical. Why would a 25-year-old woman leave midway through an MBA program to go to a country where she didn’t know a soul? 

Catherine Heald '80

But Heald only listened to her inner wanderlust. She had developed an obsession with Hong Kong while reading James Clavell’s novel Tai Pan. She just had to get there, and she would find a way to make it work.

As soon as she stepped off the plane and onto the teeming city streets, she was mesmerized. “This is the coolest place ever,” she thought. “It was East meets West. It was a British colony, but it was still 98 percent Chinese. Just walking down the street I was blown away. I reveled in getting out of my comfort zone.”

She stayed for seven years, traveling all over Asia, making many friends, meeting her first husband and starting a tech company in Hong Kong.

Today Heald helps other adventurous spirits through her company, Remote Lands, which sets up customized luxury journeys throughout Asia. The self-described “adventurer, Asiaphile and serial entrepreneur” uses her extensive knowledge and experience to take people anywhere from five-star hotels in Tokyo to a yurt in a remote corner of Mongolia and everywhere in between.

Heald, who is based in New York City, offers unique travel experiences, including a trip through the “Stans” – Kazakhstan, Kyrgyzstan, Tajikistan, Turkmenistan and Uzbekistan. On a recent trip there, she hiked along the Tien Shan Mountains in Kyrgyzstan, a stunningly beautiful range undiscovered by the West. She visited the ornate mosques in Uzbekistan’s Samarkand, one of the richest cities during the Silk Road times.

Her company also offers personalized expeditions for up to 16 travelers at a time featuring a private jet and luxury hotels. She has led tours that start in Tokyo and Kyoto and take passengers through the Philippines, Vietnam, Laos, Cambodia, Bhutan and Greece, before finally arriving in Venice. Instead of herding the entire group through a shared itinerary, each couple has their own transportation and local guide to take each traveler to whatever sites they prefer.

But Heald says there is more to luxury than elegant hotels and private jets.

“Luxury is being able to go to a small town in Japan or India, or Nepal or Bhutan, where you can meet local people and have an authentic experience. When I am in Kyrgyzstan, I’m going to be staying in a yurt,” referring to a portable, lightweight felt structure that is used by nomadic cultures.

She also specializes in travel to remote corners of Japan, another favorite destination of hers. Pre-pandemic, she traveled to Asia about six times a year, as did many of her stateside staff. Remote Lands also has an office in Bangkok, Thailand. 

Catherine Heald '80

The travelers are supported at every turn by local guides who know the regions. “We help travelers and hold their hands every step of the way.”

Heald meets with clients before designing what she calls a “bespoke” travel itinerary for them. She learns their preferences – the pace of travel, whether they want to spend time in nature or with culture and history, enjoying contemporary art or hiking. “All of these little details are so important,” she said. “We like to think that we change the world in our own tiny little way, by introducing our clients to totally different cultures and taking them outside their comfort zone, expanding their minds, and helping to really understand the world.”

Mollie Fitzgerald, owner of Frontiers International Travel in Wexford, Pa., said she has been working with Remote Lands for years. “I have long admired Catherine’s perspective on Asia. She lived there and she tells it like it is. She has astounding taste and flawless contacts.”

As a travel agent, Fitzgerald has booked trips through Remote Lands for clients, including trips to less well-known parts of Japan, a chartered yacht trip in Indonesia and a trip to Borneo, where travelers ventured into the wild and saw orangutans.

She said the private jet trips Heald organizes are outstanding. “A number of companies have private jet trips, but they are usually larger, 50 to 75 people. Remote Lands’ group size is much smaller. They are able to get into hotels that don’t take groups.”

Heald’s business was booming until March of 2020, when COVID-19 utterly devastated the travel and tourism industry, especially to Asia, where many countries immediately closed their borders.

In March of 2020, Remote Lands was forced to cancel or postpone 450 trips and furlough many staff. “It was horrible,” Heald said. By the summer of 2020, they were able to book trips to the Maldives, United Arab Emirates, Oman and Sri Lanka, some of the first Asian countries to reopen. But still the entire travel industry was down.

Now that many Asian countries are reopening and there is pent- up demand for adventure, business is ramping back up and she is hiring employees, often young people who in previous lives were lawyers, doctors, dentists or Wall Street traders. “They say, ‘Life is too short and I want to travel and do something I love,” she said.

Even when many trips to Asia were on hold, Heald was immersing herself in the culture by studying Japanese on language apps for an hour a day. “It’s hard, but when I finally get to Japan, I will test it out and it will be fun.”

“I just always want to always keep learning and traveling, reading books about all these places. I’m fascinated by geopolitics, which is obviously hugely important in the world, especially during a time like this.”

Heald inherited her love of travel from her great-grandparents, who lived in Pittsburgh and traveled the world to buy 19th-century Asian artwork and antiques.

A native of Greensburg, she transferred to Shady Side in ninth grade, e, becoming a five-day boarder. “Boarding was so much fun. It was like a pajama party every night, and we would all eat together in the dining hall.” Those bonds are still strong, thanks to Facebook. “Our class is very close-knit.”

Upon graduation, she went to New York City in 1980 to attend Barnard College, Columbia University. “I sort of fell into a computer science major, which was brand new at the time. I figured computers might become important in the future.” She was one of the only girls in her classes.

She spent a semester abroad in France and fell in love with travel as she made her way around Europe.

Upon graduation, she worked as systems analyst on Wall Street. At night, she attended an MBA program at New York University’s Stern School of Business. During that time, she began reading books by Clavell, the initial spark of her interest in Asia and the driving force behind her abrupt life change. She says she regrets not finishing her MBA but never regretted a minute of her time exploring the diverse and fascinating continent. “European culture is so similar to ours, but in Asia, it has totally different religions, languages, the alphabets are so different. Comparing Chinese to Korean to Japanese to Vietnamese to Indonesian cultures, they’re all completely different from one another,” she said.

Heald worked first for the Apple distributor in Hong Kong, and then started her first company, an e-book publisher that focused exclusively on travel. Apple was the distributor, and they bundled the CD-ROMs with their computers. When Bill Gates launched the multimedia PC in 1992, she was on stage with him to demonstrate her travel CD-ROM.

Though the company was a success, she had to overcome many obstacles to learn how to do business in China, which was far less modern in the early 1990s. “Everybody was still riding bicycles, the roads were bad, and the GDP was much, much lower,” she said. “So doing business over there was extremely difficult, but it was also fascinating.”

She met her first husband there, a famous British author named Simon Winchester. “I was in an Apple showroom and I heard this plummy accent of a gentleman asking which Mac he should buy, and that was it,” she remembered. “We were engaged in Tonga six weeks later and married on a Russian ship by the captain as we cleared international waters in 1989. We honeymooned in Singapore, Madras and Cochin. My family back in Greensburg was furious that I had eloped and left them out, but living on the other side of the globe was much harder back then.”

She was catapulted into a whirlwind social life. Thanks to her husband’s connections and his close friendship with Sir David Tang, the couple enjoyed visits from John Cleese, Jeremy Irons, Princess Diana, Lauren Hutton and members of the British aristocracy. Though they divorced after 11 years and she has since remarried, they remain good friends.

After selling the company and moving back to New York, Heald started a second tech company called Wanderlust, which created educational software for children ages 8-14. “I managed to convince MGM to license me the Pink Panther character, who starred in our animated video games where he traveled around the world and learned about all the different cultures.” She said Wanderlust was Silicon Alley’s first IPO in 1995.

Despite her success, she wasn’t in love with the tech world. “It changes so fast. You need a new business plan every six months.”

So, she asked herself: What do I love doing every morning?

Her answer? Thinking about Asia, talking about Asia, traveling to Asia. In 2006, at age 42, she started Remote Lands. She found her true calling as she sends new adventurers into the parts of the world she loves.

Every day is an adventure, for both Heald and her clients.