Journey for the Ages: How to Plan a Multigenerational Vacation Your Family Will Love

“Stephanie has left the chat” popped up in a little green bubble in our family chat group.

BARELY A SECOND HAD PASSED and my brother replied, “NO! We need you!!!” This basically sums up vacations with my family. We are a multigenerational brood of 26 people, aged 8 to 84, and I am the tour operator. Yay.

On December 30 last year, my beautiful mother turned 80, and to celebrate we all took an epic holiday with the entire clan, spending almost a whole week on the island of Boracay. Along with assistants, nannies and aides, we were more than 30 people. There was immense pressure on me to secure the rooms, curate the experiences, arrange the pick-ups, manage the restaurant bookings. It was a gargantuan task. How does one feed a picky eight-year-old, an even pickier octogenarian, and everyone in between?

The planning began as early as March 2023 and halfway through the year I found my first strand of white hair. Coincidence? I don’t think so. Worth it? Absolutely.

My parents, although still relatively healthy for their ages, are definitely much more fragile than before. Their minds are a lot less sharp, and memories for them are kind of like fallen frangipani flowers: beautiful and intoxicating for a fleeting moment, then faded and browning. The fragrance lingers ethereally in the air for them, only to be blown away by the uncaring wind.

Looking back today, just a few months hence, my father vaguely remembers the holiday, confounding it with vacations past—but like that lingering floral scent, the emotions persist. He still feels the celebration and the warmth. He was happy in the moment, admiring his radiant wife and basking in the glow of adoration and love.

My mother, who had gone through a serious medical issue just one month before her birthday, was thrilled, her heart bursting with joy at being surrounded by her loved ones. Nothing could have compared to her smile as she listened to all the heartfelt speeches given by her children and grandchildren. Or the way she laughed giddily while sipping her favourite champagne and swaying her hips to “Dancing Queen,” surrounded by the little ones.

I remember staring into the famous Boracay sunset, digging my toes into the sand and walking that fine line between anxiety that the evening wouldn’t turn out well and relinquishing control, trusting that months of planning would suffice. I took a sip of my perfectly chilled Pouilly-Fumé and sighed. The sunset was splendid, my wine was lovely, and every single person most important to me was right there. What more could I ask for?

STEPHANIE’S GUIDE TO PLANNING EPIC FAMILY HOLIDAYS

1. Properly take the lead.

If you are the designated planner, assert that you have full control. Take into account people’s suggestions, but not their complaints. If they don’t help in the planning and coordinating, they relinquish the right to complain. We once went on holiday to Bali and it was quite the disaster. The only villa that would take all of us turned out to be full of creepy, haunting antiques, and had terrible service. We all had a laugh about it later on, but at the time, it caused quite a bit of stress. However, anytime anyone complained, I just snapped back with a reminder that no one had given any other options or taken part in the planning, so here we were. We had to just roll with it.

2. Don’t book any flights except your own.

Engage a travel agent or have everyone else book their own flights. You can’t be caught up in the nitty gritty of schedules, departures, arrivals and delays. Family members have to get themselves to the destination and the rest will be managed.

3. Choose the destination wisely.

While taking a trip to Bangkok or Tokyo may sound like fun with so many things to do for all ages, this is exactly the problem. I don’t recommend city destinations for large groups, or for multigenerational travel, as people tend to go their own way, only meeting for designated mealtimes. Someone wants to go shopping, another person wants to visit a museum, this person wants to exercise—you never end up being together, just rushing to and from fleeting meetups. It’s also very difficult to move a group larger than eight people around town. Sure, you can hire a van, but the driver’ll basically always have to be on standby and you must always factor in traffic. If you can’t fit in two taxis or—better—easily walk between your key venues and attractions, choose another location.

4. It’s all about communal spaces and shared experiences.

All the beautiful spontaneous moments turn out to be the most precious, like connecting during the in-between moments of the day. Choose resorts, islands, nature escapes, villa living or boutique hotels in the middle of nowhere that facilitate those moments—keeping everyone in a confined space with a common “hang- out” area is the way to go.

Safaris are lovely getaways, because you have amazing shared experiences that you can talk about over the campfire in the evenings. Cruises are another option. I am personally not a fan—the thought of being on a boat with thousands of people makes me dizzy—but we did do it one year and it was rather fun, and many families, of course, swear by them for their multigenerational travel. You end up drinking and partying together every evening, because even on the most modern vessels stocked with activities you’re still, essentially, all trapped on a ship together, making it easy to enjoy each other’s company.

5. Make sure there’s a variety of dining options.

Feeding many people and catering to many palates can be a nightmare. Choosing a resort or destination that has many offerings is key. We stayed at Shangri-La Boracay for our last holiday, and it was incredible—the Shangri-La team was exceptional and handled all requests professionally, so I didn’t have to feel like I was playing restaurant manager, too. Knowing the resort staff were going to get people fed right was really important to my own mental health.

6. Delegate, delegate, delegate.

This is essential to being able to enjoy your holiday. If you’re a big group with a large booking, engage the help of the events team and concierge of the property. It might not be a “wedding party” but with a large enough group, it might as well be. Ask them to print itineraries for you, make the necessary restaurant reservations, and arrange logistics. They can also be your buffer. Designate one of the hotel staff as a point of contact and tell your family members to reach out to them instead of you; that way you don’t become the family concierge.

7. Leave plenty of free, unstructured time.

In our Boracay itinerary, we had shared meals, free time in between, and one big boat day. It was a good combination of togetherness and independence.

8. Don’t forget small-group bonding.

Plan some meals where you’re split up into smaller groups. Whittling the multigenerational group down to single generations sometimes allows everyone to make travel memories with their peers. Our adults-only dinner was one of the most fun moments of our trip. I was able to connect, drink, laugh and have a good time with my siblings. That’s hard to do when you’re managing parents and children and everyone is fighting for airtime. The older teens enjoyed their night out in town, while the little kids had a pizza-and-movie night. My parents were exhausted from the boat day and were happy to have lights-out at 8 p.m. A win for everyone!

9. Plan, print, release.

Once you’ve secured your itinerary, bookings, travel and contact details, dump it all into one document, print it out to put it everyone’s hotel rooms, and also share it in the group chat. Last December, I made a dramatic declaration that this was ALL the info they would ever need and that from that point onwards they were not to bother me. I was going on holiday. Any questions moving forward were simply met with a: “refer here.” Leave the chat if you must.

10. Take time for yourself.

Schedule a massage or some alone time, or leave a day later than everyone else so you can unwind. On departure day from Boracay, my flight was unexpectedly rescheduled to late in the evening, which at first made me rather upset. However, the extra time on the beach, just myself and my boys, turned out to be extraordinary. I had time to decompress, enjoy the sea, play with my kids and just savour the moment. In the future, I will always be planning it this way.

Images courtesy of Stephanie Zubiri, unless otherwise noted.

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