How On the Fly Travel Creates Unforgettable Multigenerational Family Vacations

above:A hot air balloon ride is one of many unforgettable experiences that can bring multiple generations together while traveling. From floating above the countryside to exploring a vineyard near Mount Etna in Sicily (below left), the best family trips offer something special for every generation.

Meet the travel advisor crafting multigenerational adventures families will treasure for a lifetime.

Taking in the views on a South African game drive.

For Anita Bausman, some of life’s most treasured moments happen far from home: a grandmother and her granddaughters sharing an evening at the Paris ballet before sitting to paint a famous French bridge, or three generations of a family learning to make fresh cheese on a farm high above the Amalfi Coast.

As founder and CEO of On the Fly Travel, an affiliate of Travel Experts, Inc. and a Virtuoso member, Bausman has built a career around exactly these kinds of trips. “These trips are so special because it brings families together for communal experiences, whereas their normal day-to-day lives don’t overlap,” she says.

Multigenerational travel is about creating unforgettable moments together—from cruising Paris in a vintage sidecar to arriving by seaplane in the Maldives, sharing tea and camel rides in Morocco and discovering hidden caves

Bausman has become a connoisseur of memory-making across generations, likely due to her own upbringing and wanderlust. “My heart has always been in Denmark, where I intermittently grew up, but my family went back and forth between Europe and the U.S. our whole lives, which gave me an appreciation for visiting other places,” Bausman says.“Being with my family in faraway countries was special—there’s a kind of bonding that occurs when you all collectively immerse yourself in another culture,” she adds.

Before travel became her career, Bausman spent years as an event planner and freelance painter in New York, though she was always finding reasons to pack a suitcase. “During this time, I decided that I wanted to take groups on treks in Asia, so I spent months backpacking there and around Europe,” she remembers. That desire to explore eventually led her to travel school in San Francisco, where—true to her detail-oriented nature—she had to memorize the city and give a walking tour to fellow students from a moving bus. “I love to create itineraries and experiences for people, so this went hand in hand with my love of travel,” she says. “When my kids were grown and out of the house, I dove in full time.”

Clients describe her as warm and energetic, with a planning style built on relationships rather than transactions. Bausman relies on a global network of local partners to arrange her itineraries at the best locations, many of which she has personally visited. Her trips tend to mix well-regarded accommodations with local cuisine and off-the-beaten-path adventures, personalized for a range of ages, budgets and activity levels.

“I have an ability to identify a client’s personality, travel style, comfort level and priorities, and I get to know them personally, so every itinerary reflects their interests and approach to travel,” she says. “It’s not about putting everyone in five-star hotels all the time. I want my clients to have a quintessential experience and absorb the culture where they are visiting. If they’re in Thailand, I want them to feed and bathe elephants in a protected sanctuary; if in Tuscany, they should learn to make mozzarella and tomato sauce that they can serve their own family for years to come.” Bausman’s specialty, and favorite trips to plan, are multigenerational ones.“I’m a specialist in Africa, Italy, Europe and beyond, particularly with multigen families, and I’m able to find appropriate accommodations and itineraries for a range of ages and abilities,” she says. “I also love planning milestone trips and making sure these get their proper gravitas.”

Bausman recently planned a 30-person family reunion on the Amalfi Coast, where three generations gathered at a working farm for dinner, learning to make mozzarella and limoncello from scratch before designing their own aprons to take home as keepsakes. Another upcoming trip will send a grandmother and her granddaughters to Paris, where an evening at the ballet kicks off a stay that also includes a stop at Monet’s house in Giverny to paint the iconic Japanese bridge. She’s also recently booked clients in Southeast Asia and the Caribbean, as well as a private catamaran trip for 30 people in Ischia.

For those considering working with an advisor for the first time, Bausman is candid about both the cost and the payoff. Fees vary based on the complexity of a trip—multi-city, multigenerational itineraries take more planning than a simple weekend away—but she believes the investment pays for itself. “A good travel agent will make sure you maximize your trip with a balance of fun new experiences, relaxation and special activities, plus you’ll get special perks at the places you’re booked,” she says. On the Fly Travel handles everything from a weekend hotel booking to a full bucket-list safari, along with destination weddings, honeymoons, private jet bookings, milestone celebrations, multicity international travel and sporting event trips.

That support extends beyond the planning stage. Bausman and her team are reachable 24/7, working with global partners to rebook cancelled flights or salvage dinner plans gone awry. “I use experienced on-location colleagues, and we have strong reciprocal relationships with them. There’s not a problem we can’t troubleshoot,” she says. It’s this kind of hands-on attention, she adds, that clients often don’t expect until they’ve experienced it firsthand: “Booking through a travel advisor gives you VIP amenities, unique experiences, welcome gifts that will become keepsakes and upgrades you can’t get when you book yourself.”

Many of Bausman’s clients are repeat customers, and she says she’s become close enough to some to consider them family.“I develop special relationships with my clients, especially families, and I really enjoy planning their trips because it’s personal for me,” she says, citing the idea that making memories with loved ones is invaluable, especially given everyone’s busy lives.

“Travel allows the monotony of daily life to be left behind so you can learn about and enjoy other cultures—I’ve learned this on my own family trips. Now I have a job where my goal is for everyone to make memories to cherish forever. That’s what life is all about.”

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