Why Luxury Advisors Are Now Building 5-Year Travel Plans
A shift toward long-term, life-stage planning is helping advisors secure cabins, sequence major trips, and deepen client loyalty.
Photo: Andres Medina / Unsplash
For years, luxury travel has been shaped around individual trips: a milestone birthday in Italy, a long-postponed safari, a cruise through the Caribbean or the Arctic. But as demand surges and capacity tightens across every corner of the high-end market, a growing number of advisors are shifting away from piecemeal planning.
Instead, they’re building structured, multi-year travel roadmaps—laying out not just the next big trip, but the next five. And according to several top sellers and suppliers that Luxury Travel Report spoke to at this year’s Signature annual conference, this long-horizon approach isn’t just thoughtful. It’s becoming a critical strategy for client satisfaction, loyalty, and business growth.
Few articulated the trend as clearly as Flagstaff, Arizona-based Daniela Harrison, who walks every client through a multi-year planning session before they book anything at all. “With all of my clients, when they sit down, I create five-year plans,” she said. “What is the bucket list? What special holidays do we have coming up? What needs to be done short-term based on their mobility levels, health, funding, time that they have this year, next year, the year after?” That process transforms travel from a reactive exercise into a long-term strategy—one that prevents missed opportunities and ensures that experiences requiring more stamina, flexibility, or lead time are prioritized first.
Mobility is a major driver of this shift. The advisors LTR spoke with agreed that clients often underestimate the physical demands of many bucket-list trips. The question is not only where someone wants to go, but when they’re best able to enjoy it. That consideration has pushed more advisors to sequence physically demanding destinations—Antarctica, the Arctic, Patagonia, and expedition regions—earlier in a client’s travel arc. Slower-paced trips, such as river journeys or villa stays in France or Italy, can be saved for later years when mobility becomes more of a factor.
Milestones also anchor these long-horizon plans. Retirement, major anniversaries, multi-gen reunions, and college graduations are not one-off events—they’re opportunities to design multi-stop journeys or once-in-a-lifetime sailings years in advance. Harrison said that identifying these early allows advisors to pace out the big trips and build “a whole sequence” of experiences that won’t collide with work, family demands, or limited availability. It also lets advisors lock in the most sought-after dates, cabins, guides, and ships, long before general inventory opens to the public.
Younger luxury travelers are reinforcing the trend. Advisors say clients in their 40s and 50s—many with the flexibility to work remotely—are booking farther ahead and carving out longer stretches for major trips. They’re also approaching travel with a clearer sense of sequencing, tackling big nature-driven destinations while their families are at the right ages and saving slower itineraries for later. One pattern stands out: “We’re seeing a lot of return now to the Galapagos with the grandkids,” Harrison said. “The skip-gen travel is definitely picking up.”
These multi-year plans also make it easier to safeguard the details that matter. Harrison shared how a cruise line’s automatic upgrade moved a client out of her preferred stateroom—an “upgrade” that devastated her. “She called me in tears because they couldn’t get her cabin back,” she said. “It ruined her entire trip.” Advisors say long-term planning helps them document and protect these personal preferences before inventory, promotions, or automated changes interfere.
In many cases, five-year plans now intersect with clients’ financial lives. Luxury travel has become such a meaningful category of spending that financial planners are increasingly looping in travel advisors early. Annette Stellhorn of Accent On Travel described receiving invitations to present to financial advisors’ clients—and being asked to help structure budgets for major future journeys. “Financial advisors are going to travel advisors and saying, ‘Will you help us figure out where to go, and how much it’s going to be?’” she said. The multi-year lens makes travel feel less like a splurge and more like a planned lifestyle investment, with the advisor acting as both guide and strategist.
Suppliers, too, see the benefit. Long-term planning positions clients to move into higher-value categories, especially in cruising, where loyalty tiers and early positioning determine access to cabins and world cruise categories that sell out years in advance. “It’s been really great for our clients growing into the world cruise market,” Harrison said, noting that shorter sailings in earlier years help clients raise their status. “When they’re ready to take that plunge, they actually get the cabin category they want.”
Taken together, these forces are reshaping luxury travel into a longer, more intentional arc. Advisors aren’t just planning trips—they’re planning a client’s travel life. By sequencing destinations, anticipating mobility and milestone moments, protecting loyalty advantages, and working alongside financial advisors, they’re delivering a level of foresight that clients can’t replicate on their own. For travelers navigating an era of unprecedented demand, there’s comfort in knowing that the next five years are carefully mapped. And for advisors, that roadmap is becoming one of the most powerful tools for strengthening relationships and growing a high-value business.
