Family Travel • Advice from the WOW Team
You know how it goes. The whole family gets together for the holidays, everyone's catching up, and someone says, “We should all take a vacation together next year!”
Grandma loves the idea. The cousins are excited. Someone suggests a cruise. Someone else wants an all-inclusive resort. And before you know it, there's a group chat.
Six months later, that group chat has 147 messages, four destination ideas, three different budgets, and absolutely nothing booked. 😂
Sound familiar?
Planning a vacation with extended family is different from booking a getaway for your immediate household. You're bringing together multiple households, generations, schedules, personalities, and expectations. Whether it's a family reunion, a milestone celebration, or just a chance to spend time together, the planning can get complicated.
But when it works? Those are often the trips everyone talks about for years.
We asked our World of Wonder Travel advisors for their best advice on planning multigenerational and extended-family vacations. Here are the things we wish every family knew before getting started.
How do you start planning a vacation with extended family?
Start with one or two people who are definitely going, choose a realistic timeframe, and let them lead the big decisions. Then invite the rest of the family to join.
Trying to get 15 people to agree on every detail before making a decision is a pretty reliable way to never book the trip. 😂
“Choose one or two people who are definitely going and let them take the lead. Find a trip that works for them, then invite everyone else to be part of it. You want everyone to feel welcome, but you don't need unanimous agreement on every detail to make wonderful memories together.”
That doesn't mean ignoring important needs. Ask about major budget limitations, accessibility requirements, destination concerns, and other true nonnegotiables before making commitments. But you don't need to build the entire vacation around every person's wish list.
It's okay for someone to decide that a particular trip isn't the right fit for them. The family can still move forward.
How do you handle different budgets on a multigenerational trip?
Choose a vacation that allows households to select different accommodation or spending levels, and discuss who's paying for what before anyone commits.
One family may want to keep costs down, while another is ready to splurge. Our advisor Heather loves cruises for exactly this reason: one household can book an interior cabin, another can choose a balcony, and Grandma can enjoy a suite. Everyone still gets to vacation together.
A real planning example from Carrie
Four generations, 14 travelers, and one very generous grandmother
WOW advisor Carrie worked with a family ranging in age from 1 to 70 to plan a retirement celebration. The grandmother wanted to cover most of the trip, with an overall budget of about $25,000. A villa option came in around $22,000.
Carrie suggested that the individual households contribute toward airfare, airport services, and extras. That would let Grandma give her family a meaningful shared experience without being responsible for every single expense.
This is an example of a proposed trip arrangement, not a claim that the vacation was completed or booked.
Before booking, clarify whether each household is paying separately, whether someone is gifting part of the vacation, and how shared expenses will be divided. A travel advisor can often manage individual reservations and payments, depending on the supplier and booking arrangement.
Should extended families rent one big villa or book separate rooms?
A shared villa can be wonderful for families who enjoy spending lots of time together. Separate rooms or cabins usually offer more privacy and flexibility.
A big house where everyone cooks, plays games, and hangs out together sounds lovely. But does your family actually want to share a kitchen, common spaces, and bathrooms for a week? Some families absolutely do. Others are much happier with their own space to retreat to at the end of the day.
“Have the budget conversation as a family before coming to us. Who will pay for what? Do they want a shared space, like a villa, or will everyone be much happier having their own space?”
One particularly important question: What happens if someone backs out of a shared rental?
With many villas and vacation homes, the property cost doesn't decrease just because one household cancels. Before booking, agree in writing on each household's share and what happens if someone can no longer travel. We recommend establishing that each household remains responsible for its agreed share unless a replacement is found or everyone agrees otherwise, subject to the property's actual contract and cancellation terms.
That may not be a fun conversation, but it's much better than a family argument over thousands of dollars later.
What's the best type of vacation for an extended family?
Look for destinations with plenty of options for different ages, interests, budgets, and activity levels, so everyone can enjoy the same trip without doing the same things.
Heather particularly likes Royal Caribbean for multigenerational groups. Teens can enjoy activities, grandparents can relax, younger children have age-appropriate options, and everyone can meet up for dinner. Many all-inclusive resorts offer a similar mix of relaxation, dining, and entertainment.
Destination comfort matters, too. Carrie points out that if some family members strongly object to a destination, it's better to understand that early than spend weeks trying to convince them. The core decision-makers can then choose a place that works for the people who are committed to going.
And don't forget room arrangements. Heather has helped groups look for connecting balconies, rooms sleeping five, and accommodations for grandparents with mobility concerns. Two rooms next to each other don't necessarily have a connecting door, and requests aren't always guaranteed.
“I've worked with families trying to find connecting balconies, groups needing rooms that sleep five, and grandparents with mobility concerns. These are things I always try to work through early because availability can make a big difference.”
Does everyone have to do the same activities on a family trip?
No! Plan a few meaningful shared experiences, then let each household choose how to spend the rest of its vacation.
“They DON'T have to do everything together! Seriously, I think this is so important. Plan a few things everyone can enjoy together, but give people the freedom to do their own thing too. You'll probably enjoy your time together even more!”
Maybe everyone meets for dinner, takes a special excursion, or gets together for family photos. Beyond that, the grandparents might want a relaxing morning while the teenagers head off on an adventure.
For my own family's upcoming trip, I've started an activity voting spreadsheet. I list the excursions and experiences we're considering, and everyone can vote Yes, No, or Maybe. It makes it easy to see which activities have enough interest for us to do together and which are better for just a few people.
Once the destination and main reservations are settled, you don't need the entire group to agree on every activity. That's exactly why choosing somewhere with lots of options is so useful.
Who should coordinate bookings and answer everyone's questions?
Have one or two family contacts work with a travel advisor who can coordinate the travel arrangements and serve as a resource for individual households.
Every family has that one person who starts the group chat, researches everything, reminds everyone about deadlines, and somehow becomes the customer service department for 20 relatives.
Heather has coordinated Royal Caribbean family groups involving cabins, dining arrangements, payments, pre-cruise hotels, transportation, and private shore excursions. That's a lot more than just reserving rooms.
“Probably the biggest thing is that I'm the one answering everyone's questions instead of the family member who organized the trip. They deserve a vacation too!”
Exactly. The person who brought everyone together should get to enjoy the trip, too. And this is just as true when you're organizing a getaway with several families or a group of friends.
How far ahead should you plan an extended-family vacation?
As a general planning guideline, start about 9–12 months ahead for a larger family trip, and earlier for holiday periods, popular school breaks, large villas, or specific room and accessibility needs.
It's one thing to find one hotel room. It's another to find six rooms with the right occupancy, bedding, location, and accessibility features. Starting early gives your family more time to compare options, budget, and make arrangements.
You don't need every excursion decided a year in advance. Focus first on the dates, destination, accommodations, and who is committed to going.
Save this before you start the group chat
Extended-family vacation planning checklist
- Choose one or two committed decision-makers.
- Pick a general travel window and estimate the number of households.
- Discuss budgets and who is responsible for each expense.
- Identify accessibility, room configuration, and destination nonnegotiables.
- Decide between shared accommodations and separate rooms.
- Agree on cancellation responsibility for any shared rental.
- Choose a few group activities and leave room for individual plans.
- Bring in a travel advisor to help coordinate the moving pieces.
How do you finally get the family vacation out of the group chat?
Choose a timeframe, commit to a trip that works for the core travelers, and extend the invitation. You don't need everyone's perfect itinerary before you can get started.
We hear it all the time: “We've been talking about doing this for years.” And we get it. Work schedules, school calendars, and budgets are hard enough to coordinate within one household, let alone five.
But the kids are growing up. The grandparents are getting older. And the perfect year when everyone's schedules magically align may never arrive.
Think about the cousins becoming inseparable, the grandparents sharing new experiences with their grandchildren, and the adults finally having time to catch up without rushing off to the next obligation. Those moments become family stories long after the suitcases are unpacked.
And while we've focused on extended families here, much of this advice works just as well for groups of friends traveling together.
Because years from now, nobody's going to remember who organized the airport transfers. They're going to remember the time they spent together.
Ready to get your family trip out of the group chat?
World of Wonder Travel can help you turn that “we should do this someday” conversation into a real vacation, without leaving one overwhelmed relative to organize it all.
Let's Start Planning