How to Plan a Family Vacation for Multiple Generations

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So you’ve decided to plan a family trip that includes several generations – a chance for the entire family to spend time together. Not only is this a nice “Thank You” to those who may have played a role in raising you, it’s often fulfilling to spend quality time with family or friends that you might not get the opportunity to connect with as often as you once did.

This is also the ideal time to get a picture for the holiday card without nagging everyone and buying matching Christmas sweating!

But of course this type of trip planning can be a little trickier than for just you and your family. Here are some simple tips to help you out, ensuring that all generations on this trip will have a great time.

Consider Everyone’s Needs

First and most importantly, before choosing specifics, try to put yourself in their shoes. Depending on age and health, this could be as simple as accounting for their tastes, or as valuable as knowing they will need wheelchair accessibility, special meals, or only like to walk a mile or so each day. A little bit of consideration will go a long way in the success of the trip for everyone.

Once you’ve accounted for specifics, you can dig into the planning. Below we’ll cover our favorite trips for adventuring with multiple generations.

Take a Rail Journey

Our first recommendation is a rail journey. Whether straight from your own backyard on Amtrak, across Europe with Rail Europe, or perhaps one of the world’s great train journeys on the Orient Express, a train trip is a unique and unforgettable way to travel.

Trains offer many advantages over a more standard travel plan. If any members of your group doesn’t enjoy flying or aren’t able to, a domestic train journey can be the perfect way to have a wonderful vacation far from home without the stresses of being packed into a plane or a car.

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Train journeys offer convenience of getting to see several places with less hassle of getting to those destinations. Bonus: in Europe, train stations can be some of the city’s best architecture!

Is mobility a concern? Or perhaps some of your team become tired after a relatively short time. A train trip allows everyone to see the sights and beautiful places as you slowly travel down the tracks.

Unlike airline travel, the journey truly is an experience to remember (unless you have the worst row mate ever and leave with horror stories). A well-planned train journey can be a luxurious and comfortable experience that requires very little from the travelers and offers plenty of quality time to spend with those you bring with you.

Train travel can be nostalgic for older generations, and exciting for the younger ones since it’s not as common as say a trip to Disneyland. Although, you could take a train to Disneyland to combine the best of both worlds!

Cruise into Bliss

Our next pick for travel that keeps kids, parents, and grandparents happy is a cruise. Cruises are nearly tailor-made for vacationers of all ages to enjoy. With this option, you can choose the length of stay, decide on the type of cruise – like fjords of Alaska or Caribbean beaches, and choose a boat that will keep everyone happy.

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From elegant dinners to some serious pool time, a cruise is perfect for entertaining all ages and desires.

Onboard, the kids can stay entertained with swimming, cruise programs for children, and eating pancakes with whipped cream every morning. On the subject of food, cruises typically offer a wide range of dining options, something that comes in handy when trying to please the entire family.

Relax with All-Inclusive

As a honeymoon destination, or a place to get away with small children, all-inclusive resorts are also one of our top choices for traveling with many generations of family members. The conveniences of all-inclusive resorts span all generations, needs, desires, and preferences. Even your pickiest aunt can enjoy an all-inclusive resort. Or your mother-in-law who hates nearly every travel experience.

All-inclusive resorts aim to please everyone, and this is exactly what a family vacation with several parties needs. Options for activities, dining, and the ability to be near each other without staying in the same room, are all benefits of staying at these resorts. Not to mention, you may have some built-in babysitters available so you can get away for a spa day, romantic dinner, or a swim in the ocean for two.

Once the bags are packed and everyone has made it to the gate at the airport without recreating the scene from Home Alone, an all-inclusive resort is smooth sailing. 

Find Some Meaning

Our final vacation idea is the one which may take the most, or perhaps the least research of all. When choosing a destination, one of the most rewarding journeys could likely be right in front of your nose. That special person or people you are planning this trip for, consider the events of their life. Have they always wanted to visit their mother’s hometown in Hungary but never got around to it? Were they born in Alaska, but moved away at some point and haven’t been back? Or maybe they served in the military and spent time in France, but have not been able to return. Their personal stories are some of the most valuable hints you could have to provide a beautiful memory for a lifetime for everyone involved. 

This doesn’t necessarily need to be far away to be a meaningful journey. Maybe your father grew up in the country on a farm but moved to the city in search of work and big dreams. In that case, perhaps a simple hotel rental and trying to get in touch with a few people he graduated high school with to meet for coffee could be the most touching trip he could imagine.

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A trip down memory lane may be the best option. If it’s within reach, an RV trip could be a great option.

We all have our stories, and those moments or periods in our life that shape us. Talk to that special someone and try to help them revisit those moments. The rewards can be far greater than the monetary cost of the trip itself for everyone involved.

Ready to Plan a Great Family Vacation Everyone Will Love?

We understand this can be a tricky one to plan. Which is why we’re here to help! Let us know what you’re after and we’ll find the perfect itinerary for you and your family. Reach out to us and we’ll get planning!

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