Planning a Big Family Vacation (Without Losing Your Mind)
Planning a big family vacation sounds fun… until it’s not.
And yet, I’m seeing more and more families doing it—and for good reason.
There’s a real shift happening. Families are choosing shared experiences over “stuff,” and when done well, a multigenerational trip can create some of the most meaningful memories you’ll ever have together.
Sometimes it’s grandparents treating the family to something special.
Sometimes it’s siblings finally making that long-overdue trip happen.
And often, it’s parents wanting to create lasting memories with their kids and grandkids.
The tricky part? Getting everyone there—literally and figuratively.
Different ages, energy levels, sleep schedules, and opinions on what’s “fun” can make these trips a bit… complex. But the good news is, with a little strategy, they can be absolutely incredible.
Here’s how to make it work:
Start with a Shared Wish List
Before anything gets booked, ask everyone what they’re hoping for—even the kids.
You might be surprised how much overlap there is. Beach time, good food, and not having to set an alarm tend to win across the board
This helps narrow down destinations early and makes sure the trip feels exciting for everyone—not just the loudest voices.
Choose the Right Space
Being together is the goal… but having space is what makes it enjoyable.
Think villas, vacation rentals, connecting rooms, or multi-room resort setups. That way you can gather when you want to—and have a little breathing room when you need it.
A shared kitchen, or an all-inclusive resort can also be a lifesaver for flexible meals, snacks, and different schedules.
Plan Activities (and Downtime)
It’s tempting to fill every minute, but that’s one of the fastest ways to wear everyone out.
Even the closest families need a break.
I usually recommend one or two “anchor” activities each day, with plenty of free time built in. Think structured mornings and relaxed afternoons—this tends to work really well for all ages.
Think Through Mobility
What works for a 35-year-old may not work for an 8-year-old or a 75-year-old—and that’s okay.
Just plan for it.
Look for hotels with elevators, excursions that offer flexibility, and transportation that doesn’t require long walks or tight spaces. Thinking this through ahead of time avoids a lot of stress once you’re there.
Don’t Try to Do It All Yourself
These trips have a lot of moving parts—different travelers, budgets, and expectations.
Having someone help coordinate it all makes a huge difference.
I may be a little biased but this is where working with a travel advisor really pays off. I help you think through the details, match you with the right options, and take a lot of the back-and-forth off your plate so you can actually enjoy the process.
Ready to Start Planning?
If a family trip has been on your mind, I’d love to help you put something together that truly works for everyone—from choosing the right destination to building a plan that feels balanced and enjoyable.
Reach out anytime, and we can talk through what would be the best fit for your family.