Mandy Cecchetto on Planning Family Travel From Both Sides of the Suitcase

Most travel advisors can tell you where a family should go. Mandy Cecchetto can also tell you what a Dolomites itinerary looks like when a toddler is in the mix, because she's worked it out with her own kids. Ten years into her time at Ciao Bambino, she's a senior travel advisor who is also a mom of three, and that double view shapes how she thinks about family trips.

Italy comes first

Italy is where Mandy's travel story starts. She grew up visiting the country, and her grandparents grew up there, so the connection runs deep. Her family still has relatives in Italy, and visiting them remains a priority. Ask her what she loves about the place and the answer goes well beyond the postcard list. She points to the coastlines and mountain scenery, the wine regions, the layers of history, the food, the culture and the warmth of Italian hospitality, which she calls "extra special."

After school she moved to Italy to work as a language teacher, spending her summers exploring other parts of Europe. Those years gave her a feel for living somewhere rather than just passing through, and a working knowledge of languages that still matters in her job.

From the classroom to trip planning

When Mandy saw a listing for a Ciao Bambino advisor position, she says she knew right away that it was her calling. Looking back, it was a natural fit. The role let her combine her love of travel, her years abroad and her background in languages and education into one job.

She joined the company while pregnant with her first child, so her career and her path into motherhood have grown up alongside each other. That timing has given her firsthand insight into what families need on the road, from choosing accommodations to balancing a packed itinerary with downtime. Her oldest daughter, now 9, has traveled with her since infancy and has come along on many hotel site inspections.

The best part of the job, and the hard part

For Mandy, the core pleasure is turning a family's travel wish into a real itinerary. She likes getting to know each family and then building a bespoke trip around them. The payoff comes after the trip, when clients return with stories and photos and she knows she helped them make memories they'll keep.

She also values the people around her. Her colleagues, she says, are knowledgeable, supportive and passionate about their work, and she enjoys the relationships the team has built with travel partners around the world. Those partners, she notes, shape many of the details that make a trip feel special.

The hard part is timing. Peak travel seasons are crowded, and last-minute getaways are tough when availability is thin. That's where experience and existing relationships earn their keep.

Why families bring in an advisor

Planning a luxury vacation with kids, or with several generations in tow, can eat up a lot of time. There's an enormous amount of information online, and sorting through it is harder than it sounds. Mandy's pitch is simple: an advisor handles the research, the logistics and the small details, so the family can focus on the trip itself. She says the goal is to learn who each traveler is and tailor the trip to their interests, preferences and travel style.

Ciao Bambino has been planning luxury vacations for more than 20 years. The company is part of the Virtuoso network and has preferred hotel partnerships that can bring added benefits and amenities at many of the world's best properties. Its bookings range from cruises and private bespoke trips to honeymoons and milestone celebrations. On the ground, advisors can arrange airport meet-and-greets, luggage porters, private transfers, unique activities and accommodations. Here's the thing: the real value is time. Clients get back the hours they'd otherwise spend chasing bookings, and the stress that comes with them.

A Banff and Jasper trip built around three generations

One trip Mandy considers especially memorable was a journey through Banff and Jasper for a multigenerational family marking the grandparents' 50th wedding anniversary. The group rode a gondola for views of the Canadian Rockies, paddled a canoe on the turquoise lakes, spotted wildlife in Jasper National Park and celebrated together across three generations. Bringing grandparents, parents and kids together, she says, creates a rare chance to reconnect in beautiful places.

Those trips are often the most meaningful and the most complicated to coordinate. Ages, interests, activity levels and mobility needs all have to fit together, and that's hard to balance when a family is doing it alone. It's a clear case for a planner who can accommodate everyone without turning the trip into a compromise nobody enjoys.

Back to the Dolomites

The Dolomites hold a personal chapter for Mandy. Her most recent Italy trip with her husband and kids took them back to the region, including Lago di Braies, where the two got engaged. They also marked their 10th wedding anniversary with the children there, which made the trip feel like a full circle.

Her favorite moments were simple ones: riding gondolas up into the mountains, hiking to mountain huts, watching the kids run around playgrounds framed by the scenery of Alpe di Siusi, and wandering mountain towns with pedestrian-only piazzas where the children could play and eat gelato. That mix of big scenery and small, kid-sized pleasures is a good reminder that family travel doesn't need to be grand to be memorable.

What's next on the list

Mandy's own bucket list is full. Japan and Greece are both near the top. She also wants to spend more time in her home country of Canada. This summer, the plan is the Maritimes, including Halifax and Charlottetown. The family also hopes to return to the province of Quebec and revisit Banff and Jasper with the kids.

That mix of new places and familiar ones says a lot about how family travel evolves. The first trips are about getting the logistics right. Later, the kids start shaping the itinerary, and the family starts going back to places that already hold meaning. For Mandy, the next chapter looks like more of both.