Planning a Multi Family Vacation: A Guide to Traveling with Children and Grandchildren with Ease

family walking on the beach, smiling and laughing, enjoying their multi family vacationFamilies don’t just get together at the holidays anymore. These days a multi family vacation is a popular way for grandparents too who want to spend more time with their grandchildren – and leave a lasting legacy as well. Traveling with three generations is becoming increasingly popular.

When families are spread out all over the world, what better way of creating close connections and lasting memories of times together than a well-planned trip that every generation can enjoy?

That said, coordinating and planning a family trip catered to everyone’s needs and wants seems quite daunting. But here are some guidelines to make the planning a breeze!


4 Steps to Plan the Multi Family Vacation of Your Dreams

family on their multi family vacation at the Aboard National Geographic Endeavour in Galápagos, following Theresa Jackson's luxury family travel trends

Willy and Sheila Walker and family,

Aboard National Geographic Endeavour in Galápagos


Step #1 – Plan Early

For the whole Clan

Because you are planning EVERYONE’S vacation, a year’s lead time is needed. While grandparents can be more flexible with their time, the work schedule of the adult children and school and goodness knows, the activity schedules of the grand kids really dictate when time together can happen!

Also it is best to get everyone involved in the planning – or at least the dreaming portion. Even the youngest can have an opinion – even if it is the comfy-ness of their crib!

The 1st step in planning a family vacation is looking at the calendar 6 months to a year ahead. Click To Tweet

children, parents and grand parents on their multi family vacation, participating in a safari

Seriously, though, for all to “buy in” to a trip have them make a Top 5 list of family travel destinations they’d like see along with a Top 3 list of their interests and desires of things to do. It can’t be stressed enough that ALL should feel as if their travel needs were met.

For One-on-Ones

When a grandparent is taking one grandchild at a time on their multi family vacation, it is important to enlist the kids in the planning. 

You want the trip to be fun for you both.   Sure, you can show them the world (or a smaller corner of it), but no one likes to be dragged around to all the “important” sights.

  • Build in play, downtime and time to explore a particular interest.
  • Make sure you add in activities you can enjoy together like catching an international soccer game, or taking a cooking class.
  • If the child has a particularly strong interest, take your lead from them and build a trip around that.
  • Do they love animals? A safari experience and perhaps some time volunteering at an animal refuge might be a dream come true!

zebras watched on a safari, part of their multi family vacation

When planning a luxury travel experience with your grandchild, make sure to build in fun as well as learning. Click To Tweet


Step #2 – Talk to a Travel Advisor and be STRESS-FREE

Now that you have your lists are compiled, it is time to create structure. 

A Travel Advisor not only can get you group rates for your tribe, she can also make sure everyone’s special needs are met.

No one knows your kids (and grand kids) like you do ….

BUT trust an expert to take your knowledge and work out all the details, from the big (rooms, transportation and activities) to the tiniest (who needs allergen-free pillows or has special dietary needs).

family takes a cooking class together on their multi familiy vacationBut here’s the BONUS.

Your Travel Advisor is the expert who can who takes the calls to answer questions and deal with the particulars.

The planning process should be fun – even for the lead organizer.

You should not, in other words, be left as the “head cat-herder” to make this experience happen!  Put that on someone else’s shoulders. 

Additional Bonus:

Your travel advisor can not only arrange private tours, get special rates, get you front-of-the-line access (because nothing says “get me outta here” more than a bored child on a looooong line) and other benefits you can’t get on your own, the right travel advisor can suggest things you wouldn’t know to ask for!

Let a Luxury Travel Advisor handle all the details of your family vacation and make your travel a breeze! Click To Tweet


Step #3 – Plan for times together – and times apart!

Yes, we love our family, but we can’t all be in step all of the time. 

Kids need naps, young adults will want to be very active, grandparents may dream of sitting a reading a book every so often. After all, this IS a multi family vacation, right? So make it a vacation for everyone, according to their style:

  • Plan time for activities together all will enjoy, and put these on the itinerary first as the cornerstones.
  • This way, everyone will know what to expect and when.

family in Costa Rica on her multi family vacationOn a recent trip to Costa Rica a family wanted to learn to surf together, so that was placed on a day during their beach portion.

…but It is just as important to “plan” breaks.

The family knew the older kids would want to practice their new-found skills more, while the others could rest, relax, let younger ones nap.

So plan those breaks, but plan also to keep the grand kids occupied during those times.

There are many ways to do this, from a guided activity just for the younger ones so that parents can pursue another interest and grandparents can enjoy some down time to a kids’ camp on property.


mom and dad on a special date during their multi family vacation timeMom and Dad Go on a Special Date

It is just as important to plan days or portions of days where free time can be spent apart so family units or individuals can have the opportunity to purse their own interest s – or just take a break from activity.

Imagine the fun of gathering again at the end of the day to tell stories of your luxury travel adventures!

Another option is to hire babysitters for time for mom and dad to have a special date.

For a successful family vacation, make sure that downtime and “me time” are factored into your plan. Click To Tweet


Step #4 – Expect the Unexpected

As with any large gathering or important event, it may not always go exactly as laid out. 

The weather may turn uncooperative for the day you wanted to go up the Eiffel Tower; a luggage piece might not make it to Santiago when you do.  A multi family vacation is supposed to be relaxing, fun and memorable.

  • Spend any time not exactly in the plan by sharing stories (“what your Mom was like when she was your age”) and create a legacy of calmness and flexibility in the face of the unexpected.
  • Just remember that you have a Travel Advisor as your secret weapon to fix hiccups and smooth your way. All you have to do is relax and enjoy the journey.

multi family vacation, celebrating their luxury family travel trip on beach


So here are a few ideas to get you started on planning your next multi family vacation and gathering:


#1 Make it easy with a luxury cruise or sailing.

Luxury cruises are good because they have an all (or most all)-inclusiveness about them. A floating hotel so you unpack just once. Dining and activities for all ages abound; kids and teen clubs; entertainment for all.

  1. To make your experience more exclusive, and therefore more contained, book space in the concierge levels of the ship.
  2. For more cultural immersion- particularly for the tweens and teens as well as adults, consider a family river cruise into the heart of a region.
  3. Another fun option might be to charter a yacht with a captain and crew- the ultimate in freedom!


#2 A fun way to engage everyone and meet new people who share the same interests and kids of the same ages is an organized tour.

They are great when you want a built in itinerary with planned activities and down time to explore. But don’t choose just any one.

Choose one that will get you all the great benefits and access a family needs.  (Your Travel Advisor can help).

**Here’s a good tip: Your family could take over the whole group space!


#3 Plan a theme for your multi family vacation.

What fun to be immersed in an idea! 

  • Does nature excite? There are exquisite trips to the Galapagos.
  • Adventure? Excitement abounds in Australia! The Great Outdoors?
  • Why not a luxury ranch or a privately guided trip to the great National Parks out West?

One of my clients went to Greece around the themes of culture, ancient history and Biblical history.  The kids made local handicrafts, the family ate with a Greek family; they dressed as characters from ancient Greece and acted out roles from history at the Acropolis with their very engaging scholar-guide; they followed in Paul’s footsteps one day to Corinth and beyond.   Another client took his grand kids to New Zealand because they loved loved loved movies- especially the Lord of the Rings trilogy. Not only did they visit sites where the movies were filmed, they went with private access to the filming and post-production studios where they were immersed in sound and makeup methods.  They even held an Oscar!

Anything can be done to make your family time moments to remember for always!

If you’d like to have more ease in your travel planning, I’d love to help!

You can stay informed and inspired in planning your travel in 2018 by reading more of my blogs. You can also follow me on Facebook. Twitter @enlitndjrntrvl, and Instagram @enlightenedjourneystravel. Sign up to receive the blogs and a newsletter filled with more insights and offers so you don’t miss a thing.

luxury travel advisor Theresa Jackson on one of her adventures journeys

At Enlightened Journeys Travel, we design handcrafted travel itineraries for your immersive journeys of a lifetime.

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