Stephanie Bowers Designs Multigenerational Luxury Trips That Actually Work

Stephanie Bowers

The challenge of a multigenerational trip isn’t the cost. It’s the itinerary.

Put a grandmother who walks slowly, a teenage grandson losing patience by midafternoon, and a patriarch with strong opinions about dinner into a single travel framework and you have a design problem. The right answer isn’t to split them up. It’s to find the architecture that actually works for all of them, which requires knowing what each person actually wants, not what they say they want or what someone else assumes they want.

Stephanie Bowers has built her practice around exactly this problem.

Virtuoso, the luxury travel consortium Bowers is affiliated with through her firm Singular Sojourns, ranks multigenerational family travel as the second-biggest trend of 2026. The network’s annual Luxe Report surveyed 2,485 advisors across more than 50 countries; 67 percent expect increased travel demand this year.

The wealth context explains the timing. Cerulli Associates initially projected $84 trillion in wealth transfers through 2045; revised estimates now put that figure at $124 trillion through 2048, with more than half flowing through high-net-worth and ultra-high-net-worth households. Families dispersed across cities and time zones are anchoring experiences around milestone events: 60th birthdays, 50th anniversaries, the year a grandparent still has their health. The trip carries weight. Getting it wrong is not a minor inconvenience.

What Makes These Trips Hard

SmartFlyer’s 2026 travel trends report shows six-figure luxury bookings up 26 percent year over year, with high-touch itineraries increasingly built around multigenerational families on yacht charters, safaris, and remote island stays. But the volume of bookings doesn’t solve the design problem: four generations don’t share a default preference.

Stephanie Bowers knows this from personal experience as much as client work. ‘I love doing sole-use safari lodges where a family can go and set their own pace,’ she explains, ‘because safari lodges can be a really rigid schedule: up at 4:30, out on a drive at 5:30, you must nap during these times, you must eat at this time. And that really doesn’t work with all types of clients. That comes from my personal experience of bringing my 90-year-old grandmother to South Africa.’

A standard safari lodge, even an excellent one, runs on its own schedule. A ninety-year-old grandmother runs on hers. These don’t line up. The solution she found was a sole-use lodge, where the entire property operates on the group’s terms: menus, pacing, and drive times all negotiable. ‘That schedule’s just not going to work with my 90-year-old grandma,’ she says flatly. ‘So that’s where I kind of discovered the wonders of the sole-use safari lodge.’

The principle extends beyond Africa. What works for a couple or a small family with similar-age children often breaks down under multigenerational conditions. The constraints multiply. The preferences diverge. And unlike a trip for one or two people, there’s no clean negotiation: everyone is nominally on vacation together, and the least engaged person affects the experience for the group.

Reading What Clients Actually Want

What separates a multigenerational trip that delivers from one people politely endure usually comes down to what happened before any booking began. Bowers’ intake process is built around a specific problem she’s encountered repeatedly: the person who communicates on behalf of a wealthy traveler is often not the traveler.

“Just like senior government leaders, there’s often junior staff around them that make assumptions on their behalf that are actually inaccurate,” she explains. “Actually getting to know the clients personally is really important to me: understanding their true preferences and not what people project as their preferences.”

For a multigenerational group, the problem compounds. A son might tell the advisor his father ‘loves wine.’ Whether that means he wants access to premier cru cellars in Bordeaux or just wants a good bottle with dinner on a terrace is a very different trip. A daughter might say her mother ‘wants to relax.’ Whether that means a private beach, a spa, or simply no schedule for five days requires a direct conversation with the mother.

The intake, done right, surfaces those distinctions. It identifies who in the group has hard constraints, mobility limitations, dietary needs, a teenager who checks out if not actively engaged, and it identifies what the trip is actually for. The occasion changes the architecture. A 75th birthday where the family may not gather again as a complete group calls for something different than a summer trip that happens to include three generations.

Getting Reluctant Travelers Ready Before They Go

One of the less-obvious dimensions of multigenerational planning is pre-trip psychology. Not every member of a large family group arrives at departure equally enthusiastic, and a skeptic with a seat at the table can affect the energy of a trip before the first flight boards.

Bowers describes working with a client whose traveling companion had little enthusiasm for the trip. He had traveled extensively earlier in life but had largely concluded he was done with it. He wasn’t interested in sightseeing or cultural programming. His only stated interest was food.

So she found him a book. Not a travel guide but a cultural history of the destination, told through its culinary traditions — the kind of book written for someone who wants to understand a place through what people have eaten, and why. She sent it months before departure.

By the time the trip was a month out, he was calling her. His tone had changed entirely. He had read deeply, developed opinions about which experiences mattered most, and arrived not as a reluctant addition to the group but as its most prepared member. By the time the trip ended, he was already talking about returning with his own family.

The work that produced that outcome happened months before the itinerary ran. It isn’t typically tracked as billable. But it’s often what determines whether a multigenerational trip delivers what the family needed from it, or simply what they asked for.