How to Plan a Large Group Trip Without Losing Your Mind

A real-life guide to multi-generational travel and large group vacations that actually work

Before you start a 14-person group text about “where should we go,” just call me. Trust me.

Large group travel is having a moment. Multi-generational trips. Girls’ getaways. Milestone birthdays. Cousin reunions. Everyone wants time together.

What nobody wants? Being the one stuck coordinating flights, rooms, payments, and 37 different opinions.

If you’ve ever tried to plan a big group vacation, you already know it can go from exciting to overwhelming real fast.

Here’s what actually makes it work.

1. The Right Trip Isn’t Always the First Idea

Whether it’s a multi-generational family trip or a girls’ getaway, the same rules apply.

One of my recent girls groups was excited about Greece and had about four days available.

And honestly, I get it. Greece is incredible.

But once we walked through flight time, time changes, travel days, and what they actually wanted to see and experience, we realized four days would feel rushed. They wanted to relax and explore, not spend most of the trip in transit.

So we pivoted.

They decided the Caribbean would give them more time to actually enjoy the destination without losing days to travel.

Then we looked at the calendar. October. Hurricane season.

That’s when I recommended Aruba. Outside the hurricane belt. Beautiful beaches. Easy pace. Great for multiple generations.

That’s what thoughtful planning looks like.

It’s not about saying no to a dream destination. It’s about choosing the right version of the trip so it actually feels as good as you imagined.

2. The Resort Makes or Breaks the Trip

Multi-generational vacations live or die by the property.

You need:

• Enough dining options
• Activities for teens
• Space for grandparents
• Room layouts that don’t feel cramped
• Something for everyone

I’ve steered families toward resorts with water parks because that’s what keeps the teenagers busy while grandparents relax with a drink and a book.

Balance is everything.

All-inclusives work so well for large families because no one’s arguing over dinner bills or trying to coordinate reservations for 12 people. It’s easy. It’s contained. It works.

That’s why Mexico, Punta Cana, and Aruba keep winning for family groups.

3. Not Everyone Has to Do Everything Together

This is where people get it wrong.

You don’t need to be glued together 24/7.

The best trips include:

• A few group dinners
• Maybe one excursion together
• Plenty of free time
• Space to breathe

Teenagers don’t want to be attached at the hip. Grandparents don’t want to run nonstop. Parents want a break.

You can create amazing shared memories without forcing every moment to be group time.

4. Stop Letting One Person Be the Family Travel Manager

There’s always one person who ends up doing everything.

The spreadsheet. The Venmo reminders. The “did you book your flight?” texts.

If that’s you, I see you.

When I handle multi-generational trips, I manage:

• Room blocks
• Deadlines
• Payment schedules
• Resort communication
• Special requests
• All the moving parts

So you’re not the unpaid event planner.

You’re just excited about the trip.

Why These Trips Matter

Here’s the thing.

These vacations aren’t just about beaches or pools.

They’re about:

Grandparents swimming with grandkids.
Cousins bonding.
Parents actually relaxing.
Families being in the same place at the same time.

That’s why multi-generational travel keeps growing. People want experiences together, not just more stuff.

And when it’s planned right, it doesn’t feel stressful.

It feels easy.

Ready to Actually Book It?

If your family keeps saying, “We should all go somewhere,” let’s stop talking about it and put it on the calendar.

Send me the dates. Send me the headcount. I’ll handle the rest.

You don’t need another spreadsheet.
You need a plan.