Family holidays seem like a good idea. Until Grandma wants peace and quiet, teens want theme parks, and toddlers need a nap by 2pm.
That’s the reality for millions of families every year.
And here’s the kicker…
An increasing number of families are travelling together across three (or even four!) generations. In fact, 47% now take family holidays – more than ever before.
The best news? You can certainly accommodate every generation with a little planning. Let’s dive in.
In this guide you’ll find:
- Why Family Holidays Are Booming Right Now
- Sorting The Single Trip Travel Basics
- Choosing A Destination That Suits Everyone
- Building An Itinerary That Actually Works
- Handling The Awkward Family Stuff
Why Family Holidays Are Booming Right Now
Family travel has changed. Weekends away aren’t cutting it. Families are joining budgets, aligning holiday schedules and planning one family vacation.
Why?
Traveling gives families authentic experiences they can enjoy together. 71% of grandparents have traveled with their kids and grands and even more are planning to. 71% of grandparents have travelled with their children and grandchildren.
But it’s not just the baby boomers. Millennials and Gen Z are leading the charge as well. Spending quality time with extended family has become the number one reason for booking a major vacation.
That means one thing:
Family holiday planning must entertain multitudes. It must cater to the whims of the 5 year old AND the 15 year old AND the 75 year old — all during the same 10 days.
That’s a tall order.
Do it right and you’ll have stories for years to come. Do it wrong and you’ll be apologising to family members all weekend.
No pressure.
Sorting The Single Trip Travel Basics
Planning a trip? Sort out the mundane (yet essential) details before booking flights and hotels. If you’re travelling with just one parent, start here with must-know info most families don’t think of until after disaster strikes.
Here’s what you need to lock in early:
- Passports (check expiry dates — most countries want 6 months validity remaining)
- Vaccinations and any medical requirements
- Booking flexibility in case someone gets sick
- Emergency contact details for every family member
Insurance is that dreaded thing nobody wants to think about. Until they need it. Comprehensive overseas trip cover keeps your whole family covered for lost luggage, hospital bills and cancelled bookings if disaster strikes. Single trip insurance covers you for the specific dates of your trip, making it a cheaper option to annual cover if you only travel overseas once or twice a year with your family.
A quick warning:
Senior travellers should beware of reading the small print. You may be caught out by pre-existing conditions. Grandparents often require additional medical insurance, over and above a standard family policy.
And check the age limits. Some cheaper policies won’t cover anyone over 70.
Sort this stuff first. Then you can enjoy the fun bits of planning.
Choosing A Destination That Suits Everyone
Picking the destination is where most families argue. Everyone has their dream spot.
Here’s the trick:
Avoid choosing the “ideal” location for someone. Choose a location that has something for everyone.
Think about destinations that offer:
- Beach relaxation for the older generation
- Adventure activities for teens
- Kid-friendly attractions for the little ones
- Cafes and restaurants that suit different diets
- Easy medical access (just in case)
Examples places with many boxes checked include Bali, Fiji and coastal Thailand. Places like these also exist in Europe combining old towns, theme parks and beaches.
A quick tip:
Steer clear of places that require lots of driving distances or complicated public transportation when traveling with elderly relatives or infants.
Long travel days completely kill vacations. Who wants to spend 4 hours on a bus with a screaming child and exhausted grandma?
Keep the base simple. Do day trips from there instead.
Building An Itinerary That Actually Works
Here’s a mistake families make all the time…
They over-plan. Every hour is scheduled and every attraction is crossed off the list by day 3 nobody talks to each other.
Don’t do that.
Instead, build in downtime. A good multi-generation itinerary looks like:
- Mornings: Group activity (breakfast, sightseeing, beach time)
- Middays: Downtime (naps for the littles, quiet time for grandparents)
- Afternoons: Split activities based on interests
- Evenings: Group dinner and low-key activities
That way the teens can roam free while grandma naps. Parents get 30 minutes of uninterrupted quiet time. And everyone re-connects at dinner to recount their day.
That’s the magic formula.
Another thing worth remembering:
Don’t try to cram every attraction into one trip. Enjoying 3 things fully is better than rushing through 10.
Handling The Awkward Family Stuff
Let’s be honest. Family holidays come with tension. Even the best-planned ones.
Money is usually the biggest issue.
Ok, so who is paying for what?? Are the grandparents taking care of the kids costs? Are you guys splitting the villa costs 50/50?? What about meals?? Split or separate??
Sort the money conversation before you leave home:
- Agree on a shared budget for group meals
- Decide who books and pays for accommodation
- Use a splitting app to track shared costs
- Keep receipts for anything you’re going to split later
The second awkward thing? Parenting styles.
Grandparents adore spoiling grandchildren. Parents expect bedtime rules and what food gets served to be adhered to. Those two things clash starting Day 1 unless you nip it in the bud.
A simple approach works best:
Sure, parents have the last word with their own children. Grandparents have however factored in “spoil time” on the trip — an ice cream after dinner, staying up late one night, a tiny toy from the souk.
Everyone wins. Kids get treats, grandparents feel important, parents keep control.
Bringing It All Together
Family vacation planning doesn’t revolve around picking THE place. It’s about pleasing every generation involved.
Get the basics sorted early:
- Book flexible flights and accommodation
- Sort out proper travel insurance for the whole family
- Choose a destination with variety for all ages
- Build downtime into your itinerary
- Have honest money and parenting conversations upfront
Do that and you won’t just survive the holiday. You’ll actually enjoy it.
Truthfully, these trips are the ones that become family memories for a lifetime. Children recall them. Grandparents treasure them. And parents sneak in a vacation too (occasionally).
So start planning early. Because the best family holidays don’t happen by accident.
They happen because someone (probably you) took the time to think it through properly.