If you dream of traveling someplace with your big, extended family on a trip that’s all about connection, fun, and time together, then it’s time to start planning. To help you ensure your family vacation is easy and fun for everyone, here are the questions to ask, and mistakes to avoid, when planning a multigenerational trip of a lifetime.

What one word would you use to describe your ideal family adventure? 

Before we even get into the logistics, it’s important to uncover your vision for this trip. What does your family need right now, and how can a trip help you get it? Do you want to spend more quality time together, to unplug, explore, learn, and reconnect?  Knowing your “why” will help you shape a travel experience that’s meaningful for everyone. Choosing one “theme word” ensures your trip planning stays focused on your big goals. 

Will anyone you travel with have mobility issues? 

This is an especially important question if you’re traveling with grandparents or older relatives, but keep in mind any wee ones who tire quickly or family members with special needs. You don’t want to pick a vacation style that makes some family members feel left out of the fun, so start with this question. It can guide you to the perfect destination, property, and/or cruise. Some places are more friendly to walkers and wheelchairs than others.

What ages—and developmental stages—are included among your traveling companions?

This question mostly applies to the kids. Because a thrilling zip line adventure through the jungle for a pre-tween is a total nightmare for a 5-year-old. I often see this issue come up when planning trips for my clients, because there are simply some things kids can’t handle on vacation, depending on where they’re at developmentally.  Don’t set the stage for a stress-fest by picking a vacation the kids aren’t old enough to enjoy.

How much independence does everyone want on vacation?

Together time is important, yes, but so is “me time.” If you’re traveling with aunts, cousins, grandparents, etc., consider property styles that allow different family units to have their own space with central areas where you can all gather together.  You’ll also want to keep in mind tweens and teens who crave a bit more independence. That’s hard to give them on, say, a guided tour through Morocco, but cruises with kids/teens clubs or villas with room to spread out might be a better bet. 

The next question is the hardest question of all, and it’s about money.  It’s awkward. It’s uncomfortable. But If you dream of taking a big multigenerational family trip, you have to talk about money before you depart. Otherwise, you’ll be stuck trying to manage vastly different expectations and possibly a huge bill. 

The “money question” is several questions … really, it’s a discussion.  So, here are a few cash related questions to get straight on before the trip:

  • What’s the budget, and how much can everyone afford?
  • Who is paying? Sometimes, grandparents or other family members will chip in to cover more of the cost. That’s important to figure out upfront.
  • What level of accommodations will satisfy everyone? If you’ve got 5-star folks and happy campers in the family, you may need to compromise. The general rule for luxury travel is $1,000 per person, per day.
  • What’s the actual trip cost? It goes beyond flights and accommodations—excursions, meals, and tickets add up!
  • Look at what’s included in the trip and decide what each family/traveler will pay for on their own. This could be an excellent way to manage differing budgets. Not everyone has to participate in the super fabulous (but expensive) truffle hunt or VIP museum visit! Sorting out the money question is too important to shy away from if you want your big family trip to go smoothly (and who doesn’t want that?).

Other questions to consider:

  • How far is everyone willing to travel?
  • Do school vacation schedules limit some participants availability?
  • Have you planned something everyone will enjoy?
  • Do you want everyone to unplug?  Will everyone agree to that?  Would you be satisfied with no electronics during dinner?
  • Do other’s want to help with the planning? How will you manage different ideas and expectations?

Mistakes to Avoid:

  • Planning everything yourself, no one will be happy and you’ll be resentful by the time the trip rolls around.
  • Not designating a decision maker. Think about how many times you’ve been part of a group with decision paralysis.  Ask the question “where does everyone want to go to dinner” and you may be deciding until breakfast.
  • Avoiding discussions about money.
  • Not buying tickets to must-see places or activities. Wait until you get there and you might be out of luck or you’ll be stuck in line for hours, especially with a big group.  
  • Letting stress ruin your trip.
  • Not planning for group transportation, some meals, and entertainment.  
  • Not giving yourself enough time to plan.

There’s a lot to consider when you’re planning a multigenerational family escape. The best way to plan a big group or multigenerational trip is to hire a professional travel advisor who handles all of the planning for you. With the help of a travel advisor you’re free to relax and enjoy time with those you love. 

Do you want help putting a big group trip together? Contact me here to schedule a free 30-minute trip consultation. I love helping groups of family and friends spend precious time together on an amazing vacation of a lifetime.

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