Multi-Generational Travel: A New Spin on the Family Vacation

June 4, 2024 - Meagan Palmer

Last Updated On

Recently, multi-generational travel has been on the rise. Why might that be? These days, our world is so fast-paced that it can be easy to lose track of each other in the hustle and bustle of day-to-day life. We’re all on the go, glued to technology, and just trying to keep up. Sound familiar? If it does, taking a big family trip might be the perfect way to reconnect.

Jumping Ahead

• What is Multi-Generational Travel?
• Why Multi-Generational Travel Has Become More Popular
• How Do You Plan a Multi-Generational Trip?
• Travel Insurance for Multi-Generational Travel

What is Multi-Generational Travel?

Multi-generation travel means traveling with three (or more!) generations. This is a large difference in the trend of classic family vacations, which typically consisted of the nuclear family. Multi-generational travel often means traveling with family, including parents, kids, and grandparents.

Why Multi-Generational Travel Has Become More Popular

Multi-generational travel has become increasingly popular as families look for more meaningful ways to spend time together. According to the 2025 U.S. Family Travel Survey from the Family Travel Association, 44% of families are planning trips in the next two years that bring grandparents, parents, and children together in one place. For families spread across different cities or busy with work, school, and activities, a shared vacation can be one of the few opportunities to truly reconnect. Many grandparents also enjoy the chance to create lasting memories with their grandchildren while sharing new experiences and destinations together.

 

How Do You Plan a Multi-Generational Trip?

Don’t fear the big family vacation! There are plenty of ways to make it easier to plan and even enjoyable to look forward to. Here are some of our top tips to plan the best multi-generational trip.

Start Planning Far in Advance

When a big family with diverse interests and schedules plans a trip, the best thing to do is start planning early. Yonder suggests that you start planning your extended family getaway at least 6 months ahead. Aiming for a year in advance gives you even more time to plan a truly unforgettable trip and minimizes conflict.

Who Should Organize the Trip?

Every successful multi-generational vacation needs a point person. While it doesn’t have to be the oldest family member, it often works best when one person takes responsibility for coordinating logistics, gathering input, and keeping everyone informed.

The ideal organizer is usually someone who enjoys planning, communicates well, and can balance the interests of different age groups. They don’t need to make every decision themselves, but having one central coordinator can help prevent confusion, duplicated efforts, and last-minute surprises. 

First Steps

How do you get the ball rolling? Send out a poll (we recommend Doodle) to all who will be joining to get a sense of which dates work best for all family members. Alternatively, just start asking around –whatever communication style works best for your family.

Starting a group message can help assess areas like:

• Travel preferences

• Length of trip (local day trips can be a great option too!)

• Budget

• Destination ideas

• Family-friendly activities and downtime

The more you discuss and plan together, the more everyone’s voice is heard, and expectations are met. Don’t forget to think about travel insurance! We wouldn’t want you to spend all that time planning only to have your vacation get cancelled and lose out on all your travel investment. 

Pick the Right Destination

No matter what your family is into or how much time you have to get away, we guarantee there is somewhere in the world that will work for everyone to spend time together away from the daily grind. Rather than selecting a destination that requires a lot of structured sightseeing, we recommend finding a location that offers a variety of activities to satisfy multi-generational travel. 

For example, if you head to Costa Rica, those who prefer to spend time lounging at the beach will have that option to relax. In addition, those who’d like to take part in some outdoor adventure can enjoy some thrills. Then, you can come together for mealtimes and evening hangouts. 

Pro Tip: Check out cities or areas that have access to national parks or an ocean. They often offer a new source of fun family-friendly activities for multi-generational trips.

Key Considerations for Selecting a Multi-Generational Travel Destination:

• Travel time to get to the destination: Not everyone has the ability to add in an extra few days to arrive and return from the destination. Also, some travelers don’t do well on long flights due to medical conditions or managing small children.

• Weather at the destination: Is the expectation to enjoy the beach and sunshine or travel somewhere with cooler weather? This will also help you determine the best time to visit that destination to avoid bad weather ruining the trip.

• Activities everyone will enjoy: Does your family have a variety of interests? Are the activities available at the destination suitable for all ages of those in your party? Not everyone has to participate in every single activity. However, if the purpose of your big family trip is to connect, this should be an important point of consideration.

• Average prices to visit the destination: Some destinations are more pricey than others. Consider doing some research on flight costs, hotels, taxes, and tour prices to get a general idea of normal expenses for that destination.

As long as you pick a thoughtful destination and plan to spend time together, you’re bound to have a great time! Open communication from all generations traveling will be ideal in navigating trips like this.

Where Yonder Travel Insurance Multi-Generational Families Are Traveling

While every family has different interests, some destinations consistently stand out among Yonder travelers planning multi-generational vacations.

Based on Yonder’s customer travel data, some of the most popular destinations for families traveling across multiple generations include:

• British Virgin Islands for families seeking a flexible, private vacation with opportunities for both relaxation and adventure.

• Mexico for multigenerational groups looking for family-friendly resorts, convenient travel, and activities for all ages.

• Italy for families interested in culture, sightseeing, food, and shared experiences across generations.

• Uganda for travelers looking for a meaningful adventure and once-in-a-lifetime wildlife experiences together.

• Bahamas for families seeking warm weather, easy-to-reach resorts, and a laid-back island atmosphere.

Methodology: These destinations are based on 2025 Yonder customer travel data for trips that included travelers across multiple generations.

Booking Accommodations for Multi-Generational Travel

After you’ve nailed down a destination, do some research on the lodging available there. If the destination has a plethora of offerings, then determine what type of accommodations works for your family. 

A great option for multi-generational travel is to rent a large house or apartment together (Airbnb is our favorite way to do it!) in a place that’s near a lot of different activities. Depending on the vacation rental, this can even be a cheaper option than booking a hotel.

Pro Tip: If you can swing it, have one person book the Airbnb reservation. Then have the family members pay that person back their “share” of the reservation cost. Check out our article on Airbnb’s insurance offerings and if you should consider alternatives.

If your family has more specific needs, prefers small luxuries, greater privacy, or vacation rentals are scarce at your destination, then booking hotels or resorts can better meet these needs. Plus, hotels and resorts have mostly free activities and amenities for everyone in your big family to enjoy. Be sure to read our tip on getting group discounts at hotels below!

Accommodations Influence Dining Options

Another area that might sway your decision on lodging is where and how you’ll eat. If you end up booking a vacation rental, you might be able to save money by making meals onsite, rather than going out. However, it’s best to determine if everyone’s willing to pitch in the time and money to go grocery shopping and meal planning. 

Families seeking a budget-friendly big trip can enhance their experience by discovering nearby restaurant gems for enjoyable and hassle-free dining.

Look Out For Deals

Because of the trend toward family travel, an increasing number of travel agencies and accommodations offer deals on travel for large travel parties. If your family is planning to stay at a hotel, for example, don’t book online. Instead, call the hotel and let them know your family is looking to book a certain number of rooms and ask for a group discount. Or, if you’re thinking a cruise is more your style, search for cruise lines that offer package deals for group travel.

Some airlines also offer family travel packages. JetBlue, for example, offers deals to tons of tropical vacations, from Orlando to Turks and Caicos. These deals often include airfare, hotels and resorts, and even car rentals at a discounted price. 

No matter where you want to go or where you plan to stay, a little research and a couple of phone calls could go a long way in saving your family money.

Plan Out Finances In Advance

On that note, worrying about money during the entire trip could really put a damper on your fun. If this is something you’re concerned about, try addressing who’s paying for what/when before the subject comes up during the vacation. 

There are so many ways you can go about managing expenses during multi-generational travel. In our experience, it’s definitely better to overcommunicate on budget and spending beforehand for a drama-free vacation. Here are a few ideas:

Each Household Manages Its Own Spending

If you’re planning to jump on the trend and plan a multi-generational trip and have questions about what kind of travel insurance you’ll need, check this out. We know keeping your family safe, healthy, and happy is important to you. We’re here to help make that happen!

Sometimes, it’s easier for each family to manage their own trip expenses from bookings to accommodations to food. If everyone is booking things separately, this might be the most efficient way to keep things organized. 

Plus, it gives that household more autonomy in how they spend their travel budget without having to coordinate expenses with other family members. However, if your family is making reservations together, the other methods below might be more beneficial.

Use Expense-Splitting Apps

Opting for a “pay-as-you-go” method means avoiding the hassle of managing payments and seeking reimbursement from each family member at the end of the trip. An amazing app called Splitwise allows you to create a group for the trip, and then everyone can input what they spend as they go along. 

At the end of the vacation, the app automatically balances what each person has spent or “borrowed”, and settles up the difference. It’ll tell you what you owe and to whom (or what you are owed and by whom). You don’t even have to say a word out loud about the matter! 

Designate Specific Individuals

When booking in bulk, designate specific individuals in your party to make arrangements. Then the other individuals can pay that person back their “share” of the costs. 

For example, you could have one person take the lead on booking and paying for lodging, another person handle dining expenses, and someone else manage activity or entertainment costs. This way, everyone has a specific role, making it easier to keep track of expenses and ensure everything is taken care of smoothly.

Travel Insurance for Multi-Generational Travel

Planning travel for multiple generations creates unique challenges, especially when several households are coordinating flights, accommodations, and activities. If you’re wondering how travel insurance works when grandparents, parents, and children are traveling together, read our guide to Best Group Travel Insurance Plans for Families.

“With most policies, if a family member has to cancel due to sickness, injury, or death, the rest of the family could also cancel their trip and get reimbursed,” says Terry Boynton, co-founder and president of Yonder Travel Insurance. “On the flip side, if one person cancels their vacation, the rest of the group can still travel”.

You can learn more about this option on our page regarding group travel insurance coverage. Check out our page on family travel insurance to learn what benefits are most important when it comes to traveling with kids.

Frequently Asked Questions

Tags: family