18 Tips On How To Plan A Happy Vacation With Grandparents & Kids

This post may contain affiliate links. We may receive a small commission, at no cost to you, if you make a purchase. Read Disclosure.

If you’re planning a family vacation with your kids and grandparents, then you might be wondering how it will work with so many generations, travel styles and personalities rolled up into the mix.

On the one hand, it could be an amazing bonding experience for everyone, but on the other, you could have some family members feeling bored, there may be disagreements over where to eat, and some people want more adventure than others.

It’s never going to be perfect, but it doesn’t have to be stressful. The positives of traveling with three generations far outweigh the negatives.

Just like traveling with kids is worth it despite how hard it can be, so is bringing along the grandparents for the journey.

Just think of the extra pair of hands you’ll get for help, and possibly even a date night out with your partner!

So, to make sure you receive the benefits over the cons, we’ve put together our top tips for how to plan a happy multi-generational family vacation so you can leave the stresses behind you.

Tips For Planning a Family Vacation With Kids and Grandparents

We took a road trip with my parents from Dallas to Boston for one month – that’s six people of three generations.

We hadn’t seen them since we moved from Australia to North Carolina 14 months before, so it was a wonderful opportunity to spend quality time together, especially for our kids to spend time with their grandparents.

At the same time, my parents were able to visit many places in the USA they’ve dreamed about for years, so it was more than just a catch up for them, too.

Here are some of the tips we learned from this experience…

1. Plan And Book As Much As You Can Beforehand

It’s not easy to plan for group travel. The more people you have, the more interests and diverse travel styles, and the more that can go wrong.

But our USA road trip went even better than I hoped. One reason it went so smoothly is because of the travel planning and scheduling that was done before our family vacation.

We’re usually more open ended and don’t book too much in advance, but for this trip I had it booked and organized as much as I could before we left.

Planning for travel while you are already traveling is super exhausting and time consuming, and you don’t get to feel as present when you’re constantly thinking about “what’s next?”.

I don’t recommend winging it when you are traveling in a large group, especially if that involves multigenerational travel. You want to actually enjoy the trip you’ve worked hard to create.

Engage the kids and the grandparents in the planning process so you’re all clear on what you’re going to do on your trip and are happy before you go.

2. Cater to Everyone’s Style, Budget and Interests

Before the trip, consider all travelers’ interests, bucket list dreams, travel style, travel comfort, and travel budgets.

Have a conversation about this at the beginning stage of the travel planning.

Write a list of everyone’s must do items and fit them in as best you can. It doesn’t mean everyone has to do them, but you can work a plan so those who want them most can.

We split up as a group a couple of times in Nashville and Memphis as my parents wanted to experience attractions we had previously done before.

Instead of taking the kids and having them complain, I took my parents whilst Craig took the girls to do fun kid things instead.

Consider everyone’s budgets, so you can book the right style of accommodation and attractions. Having an awareness of expected travel costs during the planning phase will help everyone have a better time on the road.

Carefully consider the time you have for your family vacation.

We had to reduce our six weeks travel plan down to four weeks once we realized our parents could only come over for four weeks.

It helped us be more strategic with our road trip direction and dropping a few places that may have been cool but weren’t essential.

You can always save more for your next multigenerational family vacation.

3. Have a Group Organizer

Choose one central person as the group organizer for the trip.

Work together to see who the best person for the job would be and then say goodbye to democracy. It will be cheaper and faster to have one boss!

Obviously, since I’m an expert in travel, we live in the US, and we were traveling with my parents, it made sense for me to take control.

Once I knew what the bucket list items were, knew what my parents were interested in based upon years of conversations with them, and what our time frame was I could work on creating a plan.

Having one person to plot this out and see all these connections makes it easier than managing different viewpoints coming in at once.

Collect the viewpoints first and then have someone put it all together.

4. Use a Google Spreadsheet for Group Travel Planning

A Google spreadsheet helps make group travel planning easier and interactive.

On our spreadsheet I had a column for:

• dates
• accommodation
• itinerary ideas
• driving distances
• notes to add in any questions, suggestions or concerns.

You can also create a folder in Google Drive to add in booking confirmations and receipts etc. for easy access while you are traveling.

This is especially handy if you have multiple people in your group taking care of different travel arrangements.

My parents could then easily check what was happening each day and tell me what looked of interest to them.

It made it easier for me to know what to schedule in and book, and whether it was cost effective to purchase city sightseeing passes or not.

For those with parents who aren’t tech savvy, stick to the simplicity of a Google spreadsheet and regular phone conversations.

If you have the group organizer this should flow easily and effortlessly.

If you like using apps for travel planning, particularly for group travel, then Travefy comes recommended as a good travel planning app for building your trip together with a group through sharing of itinerary, notes and discussions.

5. Choose the Right Mode of Transport for Group Travel

Be sure to choose the right mode of transport when you travel in a group, so you don’t exhaust everyone’s energy and finances.

Road tripping is a wonderful way to experience multigenerational travel. It’s easy, flexible, and the kids and grandparents can play games and chat.

Thankfully, we have a Kia Sedona minivan so could fit the whole family in.

Consider luggage space as well as people space. We purchased a Yakima Skybox for the top of our car so all of our luggage could fit in as well.

If you’re renting a car, will you rent one or two cars? If it is two, who will be the drivers? If you have two cars, how will you communicate and ensure you end up in the same place?

Be sure to consider all of this before you set off on your multi-generational trip.

In the cities, it can also be cheaper to catch Ubers or Lyft in a large group, rather than public transport.

After doing the math in Boston, we realized Ubers were about the same price for all of us on the train, so why not get there with ease, comfort and at a faster pace?

If you are flying together, Uber, or private car transfers will possibly be the cheapest and easiest way to get from the airport to your hotel.

6. Consider Group Travel Accommodation

What accommodation is best for multigenerational travel? Staying in hotels can get expensive when you are traveling in a group with more than 4 people as you typically have to book two or more rooms.

Unless you can get great deals, or find suites, it’s better to book apartments or villas or vacation homes like VRBO.

It will be cheaper and is nicer to share a home together.

That’s why you’re traveling together in the first place, right, to hang out? Staying in separate hotel rooms takes this bonding time away.

But you can stay in some awesome hotels, like our hotel in San Antonio right next to the Alamo.

Plus we did get sick of eating out all the time as well, so it was nice to have a home with a kitchen to cook in for dinner or breakfast. It will also save you a lot of money.

If you are booking hotel rooms, you can sometimes get interconnecting rooms, which can give it more of that homely feel.

7. Use Booking Sites You Trust

Spending hours trying to find the perfect deal to save $50 on a room can be a complete waste of your time and energy.

Can you use those four hours to create more than the $50 savings?

One way we save on time is to use booking sites we like and trust. Our preferred sites are Booking.com.

You can easily share your bookings and trip information with all the parties in your travel group.

Plus you can find apartments on Booking.com as well, which is super helpful as sometimes Airbnb can be expensive or booked out.

Sometimes if I have points, or can collect substantial points, I’ll book directly with the hotel.

The hotel chain we use the most is Hilton. It’s a brand we trust, we get discounts for being Hilton Honors Members and they have a range of property types to suit all families.

Double check your dates and prices, including extra fees like cleaning, as these can make a significant difference.

8. Purchase Sightseeing Passes

Sightseeing or city passes are a fantastic idea for popular destinations like New York City, especially if you are traveling in a large group with different interests.

They usually cater to a variety of attractions and will save you money if you plan on visiting a few.

The Sightseeing Passes, or City Passes, also help you plan your daily itinerary.

As they often have time or attraction limits, you’ll put more thought into a clearly defined schedule each day, so you can be more efficient with your sightseeing.

You’ll know what you want to see and when. Plan to visit the busiest attractions as soon as they open so you miss the lines.

If you are traveling to multiple big attraction USA cities over a 30 day period I recommend you get a the USA Sightseeing Pass which will save you LOADS!!

We have used city passes to good effect in:

9. Allow for the Unexpected

Our itinerary was booked and scheduled in advance with attractions and activities before we left.

I didn’t plan anything on our first night in Dallas as my parents were flying in from Sydney, so I knew they’d be jet lagged and tired.

But, when I realized we were staying around the corner from Dealey Plaza we decided to go for a walk to check it out. My parents are big JFK fans, so I knew they’d appreciate it.

While there we noticed the JFK Museum.

We had only an hour before closing but decided to go in and check it out as we wouldn’t be here again. We all loved it and are glad we made that spontaneous decision.

It was a highlight for Mum and Dad.

10. Book Your Tours in Advance

As we mentioned, there was no winging it on our multi-generational trip. As we’re traveling with six people, it’s essential to book tours in advance to ensure there is enough space for us.

The US is a popular destination and things can quickly book out. I almost forgot to book our ferry to Martha’s Vineyard and remembered just in time before it was full.

Same goes for accommodation in big cities, so be sure to book everything in advance at the planning stage.

Most tour companies and booking platforms have free cancelation up to 24 hours before, so you can always change your plans at a later date if you need to.

11. Plan for Meals

If I were to plan this road trip again, I would spend more time researching places to eat as this was very time consuming to do each day on our trip!

Especially as we are a family of various dietary needs.

Ask people for recommendations, read blog posts, and a simple Google search like “gluten free places to eat near x” can make your research quick and efficient.

Once you have a list of places you want to eat, you can even make a reservation.

Some places in America, particularly in popular tourist destinations like Nashville and New York, can have long wait times.

My research on Magnolia Table in Waco let me know that it was best to turn up as early as possible for breakfast after the 6 am opening.

I rearranged our plans for an early Dallas departure to get to Magnolia Table in Waco by 8am. We only had a 20-minute wait, but if we were a couple of hours later it would have been up to a four-hour wait!!

Because my technophobic Mum saw me quickly find so many wonderful places to eat, and other things on my phone as we traveled across the US, she is now using her smart phone at home to find cool places.

She was excited to tell me on the phone that she found a great gluten free cafe a 10-minute walk from her house because she said, “Google. Where is a good gluten free café?”

How technology has saved us!

12. Plan for Plenty of Restroom Breaks

Younger, and older generations tend to need frequent bathroom stops.

Rest stops can be miles apart on highways so when you see one coming ask who wants to stop and use them.

Some tours can last over an hour long so be sure to stop in at the restroom before you start your tour!

Always ask where the nearest restroom is when visiting an attraction in case you need it later. If you are doing your own walking tours in various city areas, research restrooms en route.

We were caught out a couple of times, especially in New York. A simply google search “Public restrooms near me” will help. There is always McDonalds or Starbucks.

13. Incorporate Time to Absorb the Moment

Schedule in time for coffee and cake, or meal times to sit and talk about what you just experienced.

We did so many amazing and thought provoking experiences on our road trip, it was always wonderful to sit after it and talk it over with Mum and Dad.

It’s how you process, learn greater insights and develop further curiosities.

14. Move Slowly When Traveling With Multi-Generations

My family and I didn’t follow this tip!!

My parents are both pretty fit and strong, and I only operate in one gear, which is fifth.

I was confident they could handle the pace of our USA road trip, and they did awesome, especially considering that long-flight from Australia to Dallas.

If you have a long flight to start off your multi-generational travels, you may want to have the first day of rest.

We had the afternoon and evening to have a good sleep after their arrival in Dallas and then, after an early start and the morning in Waco, had a few hours’ drive and a restful first afternoon in San Antonio exploring the Riverwalk.

Because we did move so fast, I feel like time sped by and we didn’t get time to savor one experience before loading another one on top of it.

I didn’t like this, but I don’t know the solution to it, except don’t do as much!!

But on a trip like this the objective was to do as much as we could, as it was a once-in-a-lifetime trip.

15. Consider Any Physical Challenges

My Dad had two knee replacements last year. He’s as strong as an ox and can still move well and walk long distances, but he’s also not a superhero.

We planned for more rest times and we took morning jogs out of the itinerary!!

If you are traveling with grandparents who have had replacements, be aware that you’ll be body scanned every time you go through security at the airport or at many popular attractions.

My Dad would let security know before he went through he had replacements and they’d often just go straight to the body scan.

My Mum, Craig and I have a few extra dietary concerns, so we had to consider this when planning for meals, always looking out for supermarkets as backups.

Whole Foods Market came to our rescue on more than one occasion.

16. Select one Person to be the Photographer

It can get a bit much in a large group travel experience for everyone to be taking photos. So it’s a clever idea to choose one person to take care of the photography.

It’s less time consuming and less chance of heads being chopped off. Then you can share the photos with each other at the end.

My Mum and Dad took a few photos on their own small camera, but Craig was mostly responsible for taking the photos on the trip.

He made sure to capture a lot of Mum and Dad in the moment of the travel experience, plus the typical “I was here photos” with everyone.

They were delighted with the photo memories they now have of our four-week road trip.

17. Money Tips for Group Travel

We put many of the travel expenses on our credit card, so we could take advantage of reward points accumulation.

If you have this set up and your parents don’t, or vice versa, consider doing this to help the relevant person accumulate more reward points.

Splittr is an app that simplifies the process of splitting the bill.

It works offline and integrates currency conversion, adding expenses as you go and then settling them into the home currency.

You can tag who is responsible for, or contributing, to certain bills and then a final bill is given to each traveler as a PDF.

If the grandparents are visiting from an international destination, you may want to consider them transferring money to your bank account using a transfer service like Wise.

This will save them a substantial amount of fees and low currency rates the banks typically give.

I use ofx.com all the time for my international money transfers and they have saved me thousands!

If I was to do it again, I’d put all the travel expenses on our credit card and then tell Mum and Dad to wire the money to me at the end of the trip using OFX.com.

18. Don’t Leave Home Without Travel Insurance for Multigenerational Travel

Even if you are traveling domestically, get travel insurance, especially for grandparents!

As much as you can prepare and plan for travel, there is still a lot that can unexpectedly go wrong.

You want to travel with peace of mind to know you are covered if something unexpected or an emergency happens.

Even though we had a problem free trip, and often always do, we always get travel insurance, it’s a small price to pay for peace of mind, because you just never know.

If something unexpected does happen and you are not insured, you can be up for a lot of money AND inconvenience.

So don’t shrug off this step. It’s one of the most important vacation planning tips!

What happens if:

• You need to cancel your trip unexpectedly
• There is a terrorist event
• You get sick or injured on your trip
• Your luggage is lost or stolen
• You lose your passport
• A hurricane damages your destination

Can you believe Hurricane Irma interrupted our Caribbean cruise? It cost us an extra couple of thousand dollars to get home because we couldn’t cruise back to the Port of Miami and had to fly home from Cancun.

Thankfully we had travel insurance to help us cover those unexpected costs. Get a quote. 

Final Thoughts

Now you’re all set to travel!

Go create some special memories with those you love most and appreciate this opportunity to spend quality time together.

Now to convince my parents to come over and do it all again next year! If only that flight wasn’t so long!

Pin to Save on Pinterest