Travelling with grandparents – 10 tips for multigenerational travel

As a family, we often travel together, all three generations. There’s so many good reasons to do it, and I’ve shared my top tips for making it as stress free as possible.

We all live in different states. From where I live, my parents are 4,200 kilometres (or two flights, eight hours of travel) and my sister is 3,500 kilometres away or a four-hour flight. By travelling together we all have a holiday, make memories and spend quality time together.

Multigenerational Travel Trending Up

Since covid, multigenerational travel has boomed. The trend is on the increase thanks to baby boomers who are usually retired, more active, living longer and prefer to make memories rather than just buy ‘stuff’.

More than 20.8 million travellers in the United States alone travelled on a multigenerational trip of three or more generations according to the Preferred Hotel Group. Those numbers will continue to climb, as 77 million Americans are expected to turn 65 years of age over the next 18 years.

The Family Travel Association states that 40 percent of all active leisure travellers have taken at least one multigenerational trip over the past year. Further, 25 percent of all leisure travellers are grandparents, with 37 percent travelling with their grandchildren.

Family in Positano

Positano 2016

My Multigenerational Travel Backstory

As an adult, I have travelled with my parents many times. I like to think I was ahead of the trend. In fact, I’ve done it so many times I’ve become an expert at it.

Mum and Dad visited me in 2007 when I was living in Rome, and in 2010, we met up in Lima and again in Buenos Aires while we were both travelling South America separately.

Our first overseas multi-gen trip with kids was in 2012 when my parents were both 65, along with my sister, brother-in-law and my niece and nephew, then aged five and three. Eight of us spent a week in Umbria and a week in Sicily – it was awesome, especially our dreamy stone farmhouse in Umbria. We got lost every single time we drove anywhere, but that has given us funny stories that we recount again and again.

We all have different memories from that trip. One of mine is of my toddler nephew having an absolute meltdown every time we were going out, and another is my niece cracking it when we first arrived in Italy because she was so tired and hungry. In hindsight, the kids were too young for an expensive trip like that and keeping them amused when all I wanted to do was drink Aperol spritz in the piazza was quite the challenge.

The next big overseas multi-gen trip I organised was in 2016 with my husband’s family including his sister and their 11-year-old triplet boys (yes, three boys), my 70-year-old mother-in-law, and my parents who were 69 at the time. Ten of us in total, three countries in three weeks – Cyprus, Greece and Italy.

3 boys at Myrtos beach in Kefalonia, Greece

The 11 year old triplets at Myrtos beach in Kefalonia

It was stressful to organise. Finding accommodation to cater for a big group was the first pain point. It took a lot of research. Then on the ground, finding places to eat that could fit us all, deciding on hire car configurations, deciding on activities that suited different interests and varying levels of fitness and mobility, and choosing things that met different budget levels. As much as I love in-laws, it adds a new layer of complexity and navigation when it comes multigenerational travel (you can’t be as blunt with them as you can your own blood line!).

In 2022 after international borders reopened, my sister and her family booked a family tour to Borneo and invited me along. Being desperate to travel, I immediately said yes, paid a deposit, booked flights and didn’t give it another thought for a couple of months. I barely looked at the Intrepid itinerary. All I wanted to do was see orangutans.

I didn’t have to think about anything except what to pack a week before departure, and if I’m honest, that was really stressful. We had a 15-kilogram luggage restriction due to an internal flight in Sabah. Packing for ten days in the steaming jungle plus four days in chic Singapore was major challenge. I was weighing each t-shirt on kitchen scales and basing my clothing choices on grams rather than outfit coordination, totally unlike me.

My most recent multi-gen trip was in October 2023, a girl’s trip to Italy with my 76-year-old mum, my sister, and my 16-year-old niece. It took me about 80 hours of research, possibly more, and then another 30 hours of planning for the week I was spending in Italy solo.

Family at Orangutan Sanctuary in Borneo

Sepilok Orangutan Sanctuary

Tour vs Independent Travel

The Borneo tour was the first tour I’ve done in decades, since Contiki in the 90s. All I had to do was get up and be at breakfast at a certain time and everything else was arranged. It made the trip so easy, comfortable and stress free.

That said, I should’ve checked the itinerary before booking because we stayed in a tree house in the jungle with no power and a bucket shower that I never would’ve normally signed up for. Put it this way, we had to wear leech socks. I didn’t even know leech socks were a thing before that trip. I’m pleased to report, I survived the night.

Compare that to Italy. Every time we had to go somewhere, it required us to figure it out, which we did of course, but that does take up brain bandwidth. There was stress too, like when we almost missed two trains on two occasions because our pre-booked taxi just didn’t show up. It was a lesson to pack light – it’s no fun hauling luggage on cobble streets in the middle of an Italian heatwave, then running through Rome Termini station to jump on a train.

Some people enjoy the planning process of travel. I do, but I have a limit. Finding the right accommodation is always the most time-consuming task. For the grandparents, we needed to find first floor accommodation or access to a lift, not always easy to find in European cities. Then we had to find good neighbourhoods to stay in, and there’s of course budget considerations.

Still, despite the challenges, I keep organising more multi-gen trips because travelling together is such an enriching experience. Every time we catch up, we tell stories of something that happened on one of our trips.

10 tips for multigenerational trips

  1. Agree on budgets before you book anything.
  2. Ask each traveller to list their must-dos in each destination.
  3. Agree on accommodation styles before booking. Some might love sleeping on a mattress on the floor of a tree house in the middle of the jungle, while others, erm, may not.
  4. Discuss how you’ll pay for meals out – will you split the bill, will you start a kitty, will you take turns to pay? A kitty is a good idea and has worked well for us in the past.
  5. Consider the activities and the ages of the travellers. Children under 16 are not going to be happy to sit in a trendy wine bar in Positano (unless they have an iPad), and grandparents might not enjoy spending all day in amusement parks.
  6. Consider the mobility of travellers before choosing activities, can the older travellers walk for hours, or can young children spend hours sightseeing?
  7. Work to each other’s strengths – if someone is good at reading maps, let them take charge of directions. There might be someone good at finding events or last-minute tickets, someone else might be able to always pick great restaurants, or take group photos, or grocery shopping, or driving, or cleaning up. It’s a family trip, a team effort, and it’s helpful if everyone contributes in some way.
  8. If travelling independently, book day-trips or tours on the ground, you get so much more out of an attraction and a place with a guide.
  9. It’s healthy to have time doing your own thing, you don’t have to go to every attraction together or have three meals a day together.
  10. Gelato usually solves all problems and makes everyone happy, so factor in a gelato a day.


Whether you decide to go on a tour or take the challenge to organise a multi-gen trip yourself, travelling is a privilege and if you have the opportunity to do it, take it.

5 year old girl sitting on step looking annoyed

The 5 year old, over it.

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