When the pandemic brought the world to a halt, luxury travel—like so many industries—was forced to adapt. Yet, out of the restrictions came a shift that has reshaped how affluent travelers think about their lives and their time. For James Henderson, CEO of Exclusive Resorts—a private club offering 4,500 Member families access to a $1 billion portfolio of luxury homes and experiences, the transformation was not just about destinations, but about redefining what luxury really means: community, connection, and the ability to invest one’s most finite resource—time—wisely. Discover what it means to be a member.
“Life is far too short for should haves,” Henderson told me in our conversation at Worth’s New York offices. “People devote endless hours to the pursuit of wealth, but what they really crave is time—time with friends, time with family, time well spent. The pandemic reminded us just how fleeting that can be, and it’s fueled a palpable shift toward experiences that matter, particularly in travel.”
The lockdowns of 2020 and 2021 accelerated a trend that was already simmering beneath the surface: a pivot away from just material accumulation toward experiences. For affluent families, that meant valuing private homes over hotels, seeking curated adventures over cookie-cutter vacations, and prioritizing deeper connections with loved ones. Henderson, who has worked across private aviation, yachting, and now hospitality, has watched this shift firsthand. “There’s a tremendous amount of wealth out there,” he noted. “And what has really evolved in this space is a shift from materialism to something far less tangible but infinitely more valuable: experience. Life, after all, is finite—and the point is to make it count.”
Exclusive Resorts, with its portfolio of more than 400 luxury homes and a growing array of “once-in-a-lifetime” curated journeys available only to members, was perfectly positioned to meet the moment. The company saw demand surge as families turned away from crowded hotels in favor of privacy, reliability, and flexibility. The appeal stuck. As Henderson explained, “Once people experience the Club—the service, the homes, the community—they find it hard to imagine traveling any other way.”
At its core, the model is structured not unlike a country club—at a minimum, it is a ten-year membership that could extend to thirty years—but Henderson insists the true asset isn’t real estate, it’s time. “What people are really committing to is a legacy measured not in property lines or balance sheets, but in moments—time with their children, time for themselves, time together. And because membership is inheritable, that legacy endures,” Henderson noted. “Families can pass along not just wealth, but the habit of being together, of traveling together—a gift, really, for generations to come.”
What began in 2002 as a luxury vacation club has since become something larger and more enduring: a community, a way of life. Henderson is quick to credit the members for shaping that trajectory. “People join for the travel, but they stay for the community,” he said. Today, Exclusive Resorts is as much about connection as it is about curated villas or far-flung itineraries. The Club’s journeys—to Japan, Southeast Asia, even the Antarctic—are less about ticking boxes on a map than about forging friendships that outlast the trip. With members whose backgrounds are as varied as the destinations themselves, these relationships often become as valuable as the travel itself. “It’s like a reunion,” Henderson said. “We bring together people with a connective energy, and it creates an extraordinary power within the Club.”
While traditional wealth advisors concern themselves with preserving and growing capital, the Club helps members maximize their most irreplaceable currency: how they spend their days. Increasingly, Henderson notes, wealth managers have a hand in the decision to join. The choice often comes down to whether to buy yet another second—or third —home, or to gain access to hundreds of them without the burdens of ownership. “From a wealth manager’s perspective, does it really make sense to take four or five million dollars out of a portfolio and put it into a home you’ll use six weeks of the year?” Henderson asked. “Or do you join Exclusive Resorts, where you have access to a whole portfolio of homes and experiences without the headaches?”
For advisors tasked with helping clients live more holistically—balancing financial security with health, wellness, and fulfillment—this model resonates. Henderson added, “Most wealth managers are deeply involved in their clients’ lives. If you can open doors to connections and experiences that make those lives richer and more meaningful, that’s incredibly additive.”
The philosophy of building connection is not unique to Henderson. It runs deep into the DNA of the company through its chairman, Steve Case, the co-founder of AOL—who first joined as a member before acquiring Exclusive Resorts in 2003. In the 1990s, Case helped introduce millions of Americans to the online world, creating one of the first large-scale digital communities. AOL wasn’t just an internet service—it was a portal into a new kind of connection, where people could meet, communicate, and collaborate in entirely new ways. Today, Case is still in the community-building business, but with a different kind of infrastructure. Through investments, real estate, and philanthropy, he has turned his attention to building physical communities—whether revitalizing overlooked startup ecosystems in the American heartland or creating sustainable resorts and branded residential enclaves in Costa Rica and Hawaii.
Exclusive Resorts fits squarely into that vision. Just as AOL pioneered digital belonging, Exclusive Resorts creates real-world belonging among its member families. For Case, that continuity is no coincidence: it reflects a lifelong belief that shared experiences—online or offline—shape stronger individuals, families, and societies.
That philosophy has guided the company’s expansion as well. Under Henderson’s leadership, Exclusive Resorts has diversified beyond its core club into businesses that extend its reach in the luxury travel ecosystem. The strategic agreement with Accor to take a controlling interest in onefinestay, a high-end villa rental brand, brought new flexibility to those not ready for a long-term commitment but still seeking curated, trusted options. At the same time, the company launched a new branded residential vertical, beginning with a 20-home development at Punta Cacique in Costa Rica, designed for members who want extended stays or permanent homes infused with the brand’s service ethos. Some of those homes may flow back into the club’s portfolio or onefinestay’s network, creating a seamless ecosystem across ownership, rental, and membership.
“There will always be people who want to invest in bricks and mortar,” Henderson said. “But unlike the traditional vacation home, our branded residences come with a team that manages the details—maintenance, rentals, everything. After twenty years of running a $1-billion real estate portfolio, ownership comes with permanence—but also peace of mind.”
Looking ahead, Henderson envisions Exclusive Resorts as the LVMH of travel and hospitality: a multi-brand platform encompassing club subscriptions, villa rentals, residences, and curated experiences. To help accelerate that vision, the company has, for the first time, welcomed outside investors like Kemmons Wilson Companies (KWC)—providing capital that will support acquisitions and expansion into adjacent categories. Henderson hinted at future moves into curated travel companies and concierge services, as well as broader arenas like wellness, philanthropy, and longevity. “Our mandate is to help members live richer, more meaningful lives,” he said. “It’s beyond wealth. It’s about giving people the ability to invest their time wisely.”
Post-pandemic, the definition of luxury has shifted. It is no longer just about exclusivity or opulence. It is about curation, community, and connection. For Henderson and Case alike, that means helping members not only find the perfect villa or bucket-list adventure, but also the people with whom to share it. “You can always make more money,” Henderson reflected. “But you can’t make more time.”
In that philosophy lies the essence of Exclusive Resorts’ vision—and perhaps the future not just of travel, but of how the affluent live, spend their time, and define what matters.
