More and more of the family trips I plan include three generations. Sometimes it is the parents calling, sometimes the grandparents, but the request is the same: one trip, everyone together, and a week that works for a six-year-old and a seventy-year-old at the same time.
Mount Pilatus (Pilatus-Kulm) near Lucerne, Switzerland
Photo©: Anna Fishman / Olegana Travel Boutique
That is the real art of multigenerational travel. Each generation wants something different from the same day, and the trip only works when the pacing, the rooms and the meals are planned with all of them in mind. Here are the ten rules I follow when I plan a trip with kids and grandparents.
Lake Como vacation in northern Italy
Photo©: Anna Fishman / Olegana Travel Boutique
My 10 tips for stress-free European vacations with kids
1. Choose a destination that works for every age
Bellagio on Lake Como, Italy
Photo©: Anna Fishman / Olegana Travel Boutique
Start with the flight. A direct flight under eight hours is kind to both a restless child and a stiff back. From Newark, Portugal, Italy and Cancun are some of the easiest choices from NYC/NJ airports, which is why they top my list for three-generation trips.
Then think about terrain and climate. Steep hill towns and July heat wear out grandparents fast. Shoulder season and flatter, walkable towns keep everyone going. If Portugal is on your mind, my guide to Portugal with kids covers the regions I use most.
2. Book rooms that give everyone their own space
Charming Portuguese streets with traditional arched walkways and a nearby children’s playground.
Photo©: Anna Fishman / Olegana Travel Boutique
Connecting rooms, a suite with a separate living room, or a villa with a private wing make all the difference. Kids go to bed early. Grandparents often want quiet mornings. Parents want an hour to themselves after bedtime.
Everyone under one roof, with a door to close: that is the formula. These rooms sell out first, so this is the one part of a family trip I lock in early.
3. Pick a resort built for all ages
The Rhine River in Cologne and the historic Hohenzollern Bridge in the background.
Photo©: Anna Fishman / Olegana Travel Boutique
The best family resorts have a kids club for the little ones and a quiet pool or adults-only area for the grandparents. Check the kids club age range before you book, because many start at age four and some don't take toddlers at all.
For beach weeks, my roundup of the best all-inclusive resorts in Cancun for families is a good place to start.
4. Plan one anchor activity a day
Anna and Oleg with their adorable sons
Photo©: Anna Fishman / Olegana Travel Boutique
Pace the trip for the youngest napper and the slowest walker. One good thing a day, in the morning when everyone has energy, then a long lunch and a slow afternoon.
A cooking class, a boat day or a farm visit works for every age. A four-hour museum marathon works for nobody. My guide to Tuscany with kids shows exactly how I build that rhythm for families and grandparents.
Anna Fishman enjoying a family trip with her children, sharing special travel moments and exploring new destinations together.
Photo©: Anna Fishman / Olegana Travel Boutique
5. Avoid long layovers and long airport walks
Connections are hard on anyone, and harder with a toddler and a grandparent with tired knees. Airports like London, Paris, Madrid, Frankfurt and Zurich involve a lot of walking between check-in, security and the gates. Running to make a connection with a small child is no one's idea of a vacation.
If anyone in the family would appreciate it, request airport assistance when you book. It costs nothing to ask and it changes the whole travel day.
6. Book private transfers with the right vehicle
Charming cobblestone street in Cremona, Italy
Photo©: Anna Fishman / Olegana Travel Boutique
Three generations means more luggage, car seats and sometimes a folding wheelchair or walker. Book a private transfer with a vehicle sized for all of it, and a step height grandparents can manage.
Nobody should be navigating a taxi line in a new language after an overnight flight.
7. Make lunch the main meal
The Fishman family enjoying a picnic in Italy.
Photo©: Anna Fishman / Olegana Travel Boutique
Late dinners are hard on small children and on anyone who goes to bed early. In Italy, Portugal and Spain, lunch is the long, relaxed family meal anyway, so lean into it.
I book restaurants with outdoor space where kids can move around and grandparents can linger. Breakfast at the hotel and a light, early dinner keep everyone happy.
8. Build in time apart
The iconic Tower Bridge across the River Thames in London, England.
Photo©: Anna Fishman / Olegana Travel Boutique
The best multigenerational trips are not together every minute. Kids club in the morning while grandparents take a spa appointment or a guided walk. A dinner out for the parents while the grandparents take over bedtime.
My favorite: one special outing for the grandparents and grandchildren alone. It is the day everyone talks about afterward.
9. Get the right trip insurance for every traveler
Insurance matters on every trip, and even more when grandparents are traveling. Coverage for pre-existing conditions often depends on buying the policy soon after your first trip payment, so don't leave it to the last minute.
Check that medical coverage and evacuation work abroad for every member of the family.
10. Let a travel advisor coordinate the moving parts
The scenic mountain train in Switzerland with kids.
Photo©: Anna Fishman / Olegana Travel Boutique
Three households, flights from different cities, different budgets for rooms, one shared itinerary. That is a lot to manage, and it usually lands on one person.
This is exactly what I do. I coordinate everyone's flights and rooms, find the hotels that truly work for every age, and put the whole trip into one app everyone can open. If Italy is on your list, take a look at my family-friendly Italy itinerary.
My most important takeaway?
A trip with kids and grandparents is not harder than any other trip. It simply has to be planned at three different paces at once. Get the rooms, the rhythm and the meals right, and the rest takes care of itself.
Anna Fishman is the visionary and soulful force behind Olegana Travel Boutique, orchestrating transformative journeys where meticulously curated adventures meet authentic connection and exquisite, bespoke exploration.
Photo©: Dania Sander / Unique Focus Photography
Planning a trip for the whole family?
Grab time on Anna's calendar for a complimentary consultation.
FAQ - Frequently Ask Questions
-
Somewhere with a short, direct flight, mild weather and easy walking. Portugal, Cancun and the Italian countryside are three of my favorites for multigenerational travel if you are leaving from the NYC/NJ airports.
-
Connecting rooms, a family suite or a villa, so everyone is close but has their own space and their own bedtime.
-
One main activity a day is plenty. Plan it for the morning and keep afternoons open for rest, the pool or a long lunch.
-
Connecting rooms and villas sell out first, so the earlier the better. Reach out with your dates and I will tell you what is still available.