Grandparents, parents and children on one custom trip to Italy, paced for the oldest and planned for the youngest.
A multigenerational Italy vacation is the trip we plan most often, and the one that is hardest to get right without help. Grandparents who want to see Rome one more time, parents who want a real vacation, children who need to run, and a teenager who needs a reason to look up. Three or four generations, one itinerary, one pace that has to work for all of them.
Trips 2 Italy has planned multigenerational trips to Italy since 2003. We pace the trip for the oldest traveler, give the youngest an outlet every day, and choose the accommodations and the private drivers that let a family of nine move through Italy as easily as a couple. This page is how we do it, and where in Italy it works best.
Every family arrives with a different mix of ages and a different reason for going. These are the four we plan most, and each changes the itinerary.
Two grandparents and two or three grandchildren, sometimes with a parent along, sometimes without. The trip is a gift and a memory being made on purpose. We keep it to one or two bases, book accommodations where the grandparents have their own quiet room and the children have space to play, and plan every day with a private guide who is good with children and patient with everyone. Venice, the lakes and a Tuscan villa are the usual answer.
Grandparents, parents and children together, the classic and the most common. The challenge is pace: a seventy five year old and a six year old tire at different times and for different reasons. We solve it with a home base rather than a tour route, a private driver so nobody is dragged through a train station, mornings planned and afternoons open, and a villa or apartment where the generations can separate and regroup. Our family reunions in Italy page covers the version of this trip where several households come from different cities.
A seventieth birthday, a fiftieth anniversary, a retirement. There is a person at the center and a date on the calendar, and the family is gathering around both. We plan the trip so the honoree sets the pace and the family gets the celebration: a private dinner on the night itself, a boat for the day, a villa with a long table, and a photographer if the family wants one. Everyone else’s Italy fits around it.
The family is going back to where a grandparent’s parents came from, and the grandparent is coming to show them. This is the trip where a grandmother stands in the square her mother left, and the grandchildren watch. It needs research before the family flies, a driver who knows the hill roads, and days with nothing else in them. We plan it on our family heritage trips page.
Because it can hold everyone at once, which is the real test of a family destination. Italy is built around families at a table. Children are welcome in every restaurant at every hour, the food suits a picky four year old and a demanding seventy year old, and the distances are short: a grandparent can see the Colosseum in the morning and rest by two, while the grandchildren make pizza in the afternoon. The country has beaches with shade and shallow water, lakes with boats, hill towns with a bench in every piazza, and museums with a private entrance so nobody stands in line.
It also has the villas. A Tuscan estate or a farmhouse in Puglia with a pool, a kitchen and enough bedrooms for three generations is the single thing that makes a multigenerational trip work, because it gives every generation somewhere to be without leaving the family. We hand select them for the family traveling.
By building each day in layers rather than as a single line everyone has to follow. Morning: one planned thing, usually with a private guide, that the whole family does together. Midday: a long lunch, which is the Italian way anyway. Afternoon: the generations split. Grandparents rest or take the driver to a garden or a church. Parents get a wine tasting or a walk. Children get the pool, the beach or a tour of a local monument. Evening: dinner together, at a table that can seat everyone.
We choose one base for most of the trip, with a private driver on call, so nobody packs and unpacks more than twice. We pick accommodations with the oldest traveler in mind, ground floor rooms, an elevator, a short walk to the square, and the youngest in mind, a garden, a pool, a kitchen for early breakfasts. And we leave whole days empty, on purpose, because a multigenerational trip that is scheduled to the hour is a trip nobody enjoys.
Children get Italy at their height, with activities built for them. They ride a gondola, feed the pigeons in a piazza, make gelato with a maestro, hunt for the lions hidden all over Venice, climb the Leaning Tower, walk through Pompeii with someone who tells them about the volcano, collect eggs on a Tuscan farm, and swim in a sea that is warm from June to October. Kids between six and twelve remember all of it for the rest of their lives, which is why so many grandparents choose this age to take them.
Grandparents get Italy at their pace, with a driver, a guide and a family around them: the sightseeing, the landmarks, the cuisine and the tradition of a long table, and the bonding that only happens when three generations share one week. They get the Vatican with a private entrance and a bench, the Uffizi in an hour with the best guide in Florence, a boat on Lake Como with a blanket, a vineyard lunch that lasts all afternoon, and the sight of their grandchildren in the places they always wanted to show them. The trip is planned so the oldest traveler never has to choose between keeping up and staying behind.
Everything on the ground in Italy, coordinated by one team. Accommodations hand selected for the ages traveling, whether that is a villa with a pool, an apartment building where each household has its own door, or a hotel with connecting rooms. A private driver from the airport onward and on call through the trip. Private guides for the sights the family chose, with timed entries so no grandparent stands in line. The experiences for each generation, from a cooking class to a boat to a farm morning. Restaurant reservations for a table of ten. A day by day itinerary with every name, time and address. And our planners, reachable for the whole trip.
Nine travelers is where a multigenerational trip becomes one of our group trips to Italy, with its own planner and each household booking and paying separately. Below nine we plan it as a private family vacation. Either way, the family never carries the logistics.
One base, always, for a family with children and grandparents. These are the bases that work, and what each one gives the generations.
Best for three generations, and the strongest answer to almost every multigenerational brief. A villa with a pool between Florence and Siena, a private driver for day trips to the hill towns, a farm morning for the children, a wine tasting for the parents, a garden for the grandparents, and Florence’s museums an hour away with a guide. See the Tuscany travel guide.
Best when the grandparents are the ones to plan around. The lake does the moving: a private boat to Bellagio and Varenna, a garden villa to walk through, a funicular for the view, a swim for the children off a lakeside lawn. Nobody climbs anything they do not want to. Our Lake Como travel guide covers the towns families base in.
Best for a summer trip with school age children and grandparents who want warmth. A base near Taormina or Cefalu, a beach with shade and shallow water, Mount Etna by cable car for the family that wants it, Greek temples for the ones who want history, and a private driver for all of it. Our summer guide to a multigenerational family trip to Sicily shows how three generations covered the island. See the Sicily travel guide.
Whether the grandparents will be able to keep up. They will, because the trip is paced for them and the driver is on call. Whether the children will be bored. They will not, because every afternoon has a pool, a beach, a boat or a farm in it. Whether everyone has to do everything together. No, and the itinerary is built so they do not. Whether it is too many people to plan for. A family of twelve across four generations is a trip we have planned many times, and the logistics of moving a party that size are covered in our article on group travel to Italy.
A relaxed 10-day, land-only family journey through Italy’s south: Rome by electric tuk-tuk, seaside Gaeta, the ruins of Pompeii, the island of Capri, the street food of Naples, and
Bring the whole family home to Abruzzo. A relaxed 11-day multigenerational journey through ancestral hill towns, shared kitchens and castle-crowned peaks, from Sulmona and L’Aquila to a grand finale
A bright 10 day summer family vacation in northeastern Italy, combining Udine as a relaxed home base with hands-on cooking, storybook day trips, and a coastal finale in Trieste.
Three or more generations of one family traveling together, typically grandparents, parents and children and sometimes great grandparents or adult grandchildren, is what we plan as a multigenerational vacation. In Italy it usually means one home base, a villa or an apartment building where the generations can be together and apart, a private driver so nobody manages luggage or train stations, and days paced for the oldest traveler with an outlet for the youngest.
Tuscany is the strongest answer for most families, because a villa with a pool between Florence and Siena gives every generation somewhere to be, with the hill towns, the farms and Florence’s museums all within a private driver’s reach. Lake Como suits a family where the grandparents set the pace, because the boat does the moving. Sicily and Puglia suit a summer trip that wants warm water and space. Rome and Venice work as a two or three night start before the family settles into a base.
We plan one shared activity in the morning with a private guide, a long lunch, and an afternoon where the generations separate: rest or a garden for the grandparents, a pool, a beach or a farm for the children, and a walk or a tasting for the parents. Dinner brings everyone back together. We choose accommodations with ground floor or elevator access for the oldest travelers and a garden or pool for the youngest, keep the family to one or two bases, and leave whole days open.
Yes. We hand select villas, farmhouses and apartment buildings that can hold a family of eight to sixteen, with enough bedrooms for each household, a pool, a kitchen for early breakfasts, and a table long enough for everyone at dinner. We also arrange a private chef for the evenings the family wants to stay in, a driver on call for the days out, and childcare when the parents want an evening to themselves.
As large as the family. Up to eight travelers we plan it as a private family vacation. From nine travelers it becomes one of our group trips to Italy, with its own planner, each household booking and paying separately, and our own personnel on the ground in Italy. Either way the family never carries the logistics, and a family of twenty across four generations is a trip we have planned many times.
Tell us how many households, the real ages of the youngest and oldest travelers, roughly when, and what the family cares about most, using the planning form on this page or by calling our Houston office at 713-952-4055. A Trips 2 Italy planner will talk through the pace, the base and the places, then send a first itinerary for the family to react to. We refine it together and then book everything.
A trip with the grandparents and the grandchildren is the one the family will talk about for the rest of their lives. Since 2003 Trips 2 Italy has planned Italy for three and four generations at once. Tell us who is coming and we will build the rest. Call 713-952-4055, toll free 1-866-464-8259, or start with the planning form.
The other kinds of family trips we plan, each on its own page, and the family vacations hub they all belong to.
