The Year of Families

Every year is different at Insider’s Italy.

Looking back over 37 years and thousands of independently designed itineraries, I have never noticed a particular pattern from one year to the next. Most years combine honeymooners, art lovers, smaller families, couples, long time Italophiles and first time visitors.

This year is different.

This is the year of family groups.

In recent months I have planned journeys for families of five, seven, eight, nine, eleven, thirteen and, this week, forty-one travelers.

What fascinates me is not the size of the groups but their origins.

Every one of them began with a single traveler or small family group whose journey I had planned years earlier…

… sometimes decades earlier. Sometimes the first was an anniversary trip, a honeymoon, a second visit to Italy, or another important celebration. Their travels with me were not recent. Most took place twenty or more years ago. Yet when it came time to organize a journey for children, grandchildren, siblings, or lifelong friends, they remembered Insider’s Italy and came back.

That continuity is one of the great privileges of doing this work.

Over the years I have watched travelers return at different stages of their lives. An unmarried couple becomes a family of five. Parents return with grown children. Travelers I first met decades ago now ask me to design journeys for grandchildren who were not even born when we first worked together.

One family in particular captures what has made this year so memorable.

As I write, forty-one members of the same family, ranging in age from three to eighty-eight, are on the second day of a seven-day journey through Tuscany. They have come from across North America to celebrate a sixty-fifth wedding anniversary. Four generations are traveling together.

This evening, after aperitivi...

… they will gather for a formal anniversary dinner in the historic Florence house hotel that they have reserved exclusively for the week.

A professional singer I found especially for the occasion will perform popular songs from 1960, both Italian and American, recreating the soundtrack of the year their life together began. At the conclusion of dinner, an anniversary Charlotte cake decorated with 65 wild strawberries will be assembled before their eyes.

Earlier today they spent the day in Chianti with artisan winemakers, exploring vineyards and cellars, and then enjoying a true zero-kilometer lunch prepared from ingredients grown and produced on the estate itself. Wines, olive oils, sheep’s milk cheeses, vegetables from the gardens, and traditional local dishes formed a meal that reflected the agricultural traditions of the region as much as its cuisine.

And this is only the beginning.

In the days ahead, the youngest members of the family will participate in drawing and painting workshops created specifically for them. Others will explore Florence with one of my most beloved docents, visiting artisans, markets, and workshops rarely encountered by ordinary visitors. In small groups and with my docents, the family will discover neighborhoods, churches, gardens, and artistic treasures that lie beyond the familiar tourist routes yet reveal much about Florence’s cultural life.

Planning for forty-one people is not simply planning a larger trip.

It means creating a journey for children of many ages, parents, grandparents, and great-grandparents alike. Interests, energy levels, mobility, and expectations vary enormously. The challenge is ensuring that every traveler feels that the journey was designed exclusively with them in mind.

The larger the group, the more important it becomes that no traveler ever feels part of a generic group trip.

Whether I am planning for two travelers or forty-one, every itinerary begins the same way it has for nearly four decades: with a conversation. Before I recommend anything, I take great care to understand who is traveling, what interests them, what they hope to experience, and what kind of journey will be meaningful to them.

The logistics behind these journeys are substantial, though ideally invisible.

Multi-generational travel requires careful coordination of arrivals, departures, transportation, guides, restaurant reservations, private visits, and countless details that most travelers never see. My role is to ensure that all of those moving parts work together seamlessly, allowing families to focus on being together rather than on the mechanics of travel.

The planning itself is painstaking. The level of preparation, research, and intellectual curiosity that goes into these itineraries is often closer to what one might expect from an exceptional academic tour than from conventional travel planning. Every recommendation is considered in relation to the travelers themselves: their interests, pace, previous travels, curiosities, and expectations.

Perhaps what most distinguishes Insider’s Italy is that I do not outsource any part of this process.

I do not hand travelers to a planning team. I do not pass responsibility to assistants, destination specialists, or local representatives. Every itinerary is designed by me personally. Every recommendation, reservation, introduction, adjustment, and refinement passes through my hands.

From the first conversation until travelers return home, there is a single point of responsibility and a single person who knows every detail of the journey.

Equally important, I remain available throughout the trip itself. Because I live and work here, I am operating in the same time zone as my travelers and the people with whom I work. Questions do not disappear into an anonymous support system. Whether a reservation requires adjustment, a transfer changes unexpectedly, or a traveler simply needs advice, I can be reached directly.

The people with whom I work are equally important.

Over decades in Italy I have built relationships with historians, archaeologists, art historians, conservation specialists, winemakers, farmers, artisans, and local families whose knowledge cannot be found in guidebooks. Their contribution shapes every journey.

Amalfi is one example.

I have been visiting Amalfi since early childhood, and it remains a place of close friendships and long relationships. My clients do not simply arrive for a tour. They may spend time in kitchen gardens and vineyards that have sustained local families for generations, cook dishes rooted in seasonal traditions, and meet people whose connection to the landscape extends back centuries. Until relatively recently, some of these families still walked the 1,500 steps between the hills and the sea as part of daily life.

These are the experiences that travelers remember. The care that shaped every detail, the people they met, the stories they heard, and the feeling of having been introduced to a world that would otherwise have remained invisible.

Perhaps that is why all this year’s groups began with someone who traveled with me decades ago.

Across Italy — from Sicily to Puglia, from Venice to Amalfi to Florence, Rome, and Tuscany — I find myself planning journeys whose origins often lie many years in the past. When the time came to plan something larger, more personal, and deeply meaningful, my clients came back, this time to share the experience with those whom they love most.

As their planner, I can imagine no greater compliment than that.