✈️ How to Plan a Multigenerational Vacation (Without Losing Your Mind)
There’s nothing in the world I love more than having all the people I love most in one place. Traveling is my passion—and sharing those experiences with my whole family makes them even more meaningful. But let’s be honest: planning a trip for multiple generations can be challenging.
Right now, I’m planning a trip that includes my parents, my three brothers and one sister and their partners, my wife’s mom, my sister-in-law and her boyfriend, and our son. Plus an aunt, a few nieces and nephews, and few of their friends. That’s a lot of people. And where are we going to celebrate this destination reunion? We’re going to sail across the Caribbean onboard the Carnival Celebration. ! 🎉✨
No matter your destination, the same rules apply. Whether your group is four or forty, here are the most common mistakes I see when planning multigenerational travel—and how to avoid them.
❌ Mistake #1: Not Including Everyone in the Planning
If you’re reading this, chances are you’re the designated planner (just like me). But even if your family says, “I don’t care, you decide,” trust me—they care. And those are often the first people to complain later.
✅ What to Do Instead:
Ask each traveler to choose one “must-do” activity. Make a list, build a flexible itinerary around it, and don’t worry if not everyone participates in every activity. The goal is for everyone to have at least one unforgettable moment.
❌ Mistake #2: Overplanning
When you’re trying to please everyone, it’s tempting to cram the itinerary. But especially if you’re traveling with little ones or older adults, too much can lead to burnout (and meltdowns).
✅ What to Do Instead:
Stick to three activities a day—one morning, one afternoon, and one evening option. Anything else is a bonus. Have a list of backup ideas based on your location so you’re never scrambling.
And always, always build in downtime. A relaxed morning with coffee, a midday nap (even for adults!), or time to explore independently can make a huge difference.
❌ Mistake #3: Spending Every Single Moment Together
Yes, you’re there to bond—but togetherness 24/7 isn’t always the best idea. With different personalities, interests, and energy levels, some breathing room can actually make the experience better.
✅ What to Do Instead:
Plan time apart. My brother and I love traveling together, but even I need a break from his habit of chatting with every single person we meet. My other brother? He refuses to plan or wake up early. So I build in flexibility—everyone knows where I’ll be and when. They can choose to join or not. It keeps the peace and makes dinner conversations full of fun recaps.
❌ Mistake #4: Not Planning Far Enough in Advance
When you’re coordinating travel for a large group, flexibility becomes a luxury. Flights, villas, dining reservations, and group activities can fill up fast—especially during school breaks or holidays.
✅ What to Do Instead:
Book early. If you’re considering a villa or want multiple rooms in one resort, the earlier the better. Most properties offer flexible cancellation policies, so you can hold what you need and adjust later if needed.
❌ Mistake #5: Going to the Same Place Every Year
It’s easy to return to the place you know—especially if it’s kid-friendly and stress-free. But if your family vacation always looks the same, you may be missing out on richer, more meaningful experiences.
✅ What to Do Instead:
Think beyond the familiar. Kids can absolutely handle new cultures, foods, and settings—you just have to plan it right. Don’t underestimate their ability to adapt and grow through travel!
❌ Mistake #6: Avoiding the Money Talk
No one loves it—but skipping the budget conversation is the biggest mistake I made on my first multigenerational trip.
✅ What to Do Instead:
Start early. If it’s your trip and others are joining, lay out estimated costs up front. If it’s a shared vacation, talk to each family member one-on-one to understand what they’re comfortable spending before diving into destination decisions.
Also clarify things like:
- Who’s paying for meals?
- Are you splitting transportation or activities?
- Will one person front group reservations?
The earlier you sort out money, the smoother things will go.
❌ Mistake #7: Doing It All Yourself
Planning a group trip is a full-time job—on top of your actual job, parenting, and daily life. Coordinating flights, hotel rooms, excursions, and preferences? That’s a lot.
✅ What to Do Instead:
Let a travel advisor (like me!) take it off your plate. I specialize in multigenerational travel and think through the logistics you may not even realize are coming. And the best part? My services come at no additional cost to you—I’m compensated by the travel partners we work with.
✨ The Bottom Line
There’s no “right” way to plan a multigenerational trip—just the way that works for your family. Whether you’re dreaming of a beach resort, river cruise, national park, or international villa, I’m here to help make it seamless, special, and stress-free.
💬 Ready to start planning? Let’s find the destination that fits your family best.
📅 Click here to schedule a 30 minute complimentary consultation with me today!
📍 And if you’re still not sure where to go, check out Magical Memories: Planning the Perfect Multigenerational Vacation.
