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

Recently, multi-generational travel has been on the rise. Why might that be? These days, our world is so fast-paced 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

blue outline of arrow pointing right 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.

grandfather holding his grandson on the ground

blue outline of arrow pointing right 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.

blue circle with white number 1 in middle 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.

How do you get the ball rolling? Send out a poll (we recommend Doodle) to all who will be joining to get a sense as to 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. 

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blue circle with white number 2 in the middle 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. 

at the beach with parasailors in the air

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.

blue circle with the white number 3 in the middle 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.

blue circle with the white number 4 in the middle Look Out For Deals

Because of the trend toward family travel, an increasing amount 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.

Beach walk, family summer and children holding hands with grandparents while walking by the sea on .

blue circle with the white number 5 in the middle 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.

Beach, selfie and happy big family on vacation together in summer by seaside in Australia

blue outline of arrow pointing right Travel Insurance for Multi-Generational Travel

As you can imagine when taking a big family trip, there’s a lot more wiggle room for derailed travel plans. This is especially true if traveling with grandparents and kids. Travel insurance can protect you from losing your trip investment if you or a family member suddenly has to cancel your vacation. Travel insurance can also provide reimbursement for medical treatment, travel delays, and lost baggage during your trip.

For groups of ten or more, a group travel insurance policy can save money without compromising coverage. Plus, most policies have access to emergency assistance. This provides reassurance and immediate assistance during a travel or medical emergency. 

For multi-generational travel, group policies are ideal. Essentially, each insured individual would still have their own coverage. 

“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. Alternatively, each household could purchase their own travel insurance plan to insure their nonrefundable trip expenses and obtain medical and travel loss/delay coverage. Check out our page on family travel insurance to learn what benefits are most important when it comes to traveling with kids.

Where have you gone on a trip with more than one generation in your family? Tell us about it, and we might even share your story here on the blog! You can share on Facebook, Twitter, or Instagram (or tag us @insureyonder).

As a seasoned professional with over five years of experience in the travel insurance industry, Meagan has honed her expertise in marketing and operations working for Yonder Travel Insurance. Throughout her career, she's shown dedication assisting customers at every stage of their travel insurance journey, from the initial quote process to navigating the claims process. Her expert understanding of travel insurance equips her to provide unbiased and valuable insights, which help travelers find the best coverage and maximize its benefits.


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