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How To Avoid These 5 Common Mistakes When Planning A Multi-Generation Family Vacation

September 28, 2023

Planning a multi-generation family vacation is equally frustrating as it is rewarding. At some point in your life, you’ll have the dream of taking everyone – grandparents, aunts, uncles, cousins – on a big family getaway.

However, there are a few reasons these dreams never happen. Or it ends up being a disaster. And these 5 common mistakes are usually to blame.

Ignoring Interests and Needs

One of the biggest mistakes of planning a multi-generation family vacation is not taking everyone’s interests and needs into consideration.

Communication is key. Each generation may have different preferences when it comes to activities, accommodations, and travel pace. So, before making any concrete plans, gather information from everyone going on the vacation. What do they want to do? Is there something for everyone?

Consider creating a flexible itinerary. That way, everyone has a chance to enjoy activities they love.

Overbooking and Overplanning

In the excitement of planning a family vacation, it’s easy to fall into the trap of overbooking and overplanning every minute of the trip.

I do believe having a good itinerary is the key to success. Not only does a good itinerary help keep budgets in check, it’ll allow you to see firsthand if you’re scheduling too much before you actually get to your destination.

A good itinerary should have a mix of scheduled activities, downtime, and a little spontaneity. Overplanning can lead to exhaustion and may even cause others to not enjoy the vacation you worked so hard to put together. And no one wants that.

Ignoring Health and Mobility Concerns

Growing up, I used to spend one week every summer visiting my Grandma in Massachusetts. We’d get together with my aunt, uncle, and cousins. And we would do new things every summer.

As we got older, my Grandma couldn’t go anywhere that wasn’t wheelchair accessible. She also couldn’t spend too much time in the sun. And although there were 10 of us who didn’t have any restrictions about where we could go or what we could do, Grandma’s health was a priority. So, our activities were chosen based on her being able to come with us.

Every member of the family may have different health conditions, mobility levels, or dietary needs. Ignoring these considerations can cause discomfort, inconvenience, and resentment from the person feeling excluded.

Make sure you’re aware of any special requirements and make necessary arrangements. Choose accommodations and activities that are accessible and suitable for everyone’s physical capabilities. And if you’re planning to eat out, make sure there is something on the menu for everyone.

Underestimating Budget and Expenses

Budgeting for a multi-generation family vacation is more complicated than many realize. What may be reasonable for one may be extravagant for another.

Travel costs, accommodations, meals, and activities can add up quickly, especially for a larger group. Take the time to carefully plan and budget for all anticipated expenses, including potential unforeseen costs.

Find some way to involve everyone and establish a budget that everyone is comfortable with, so there’s no surprises down the road.

Lack of Effective Communication and Planning Ahead

I know I’m mentioned communication a lot already. But, that’s how important it is, especially while you’re planning a giant multi-generation family vacation.

As a Travel Advisor, I like the process of creating a private Facebook Group. Everyone can ask questions without feeling like they’re interrupting everyone else’s day with constant text messages. I also use a Travel Itinerary App to keep everyone informed of the itinerary, updates, and any changes that has been made to their plans, including automatic flight changes. This works well because everyone is seeing the same itinerary, in real time.

However you choose to communicate your plans, encourage everyone to address concerns or preferences early on in the planning process. That way, everyone feels like they had a part in the planning process. And at the end of the day, all we really want is a harmonious and enjoyable vacation for everyone.

Got questions? Feeling a bit anxious? Not sure where to begin? We help families, just like yours.

Planning an entire vacation can be overwhelming. But, here’s the good news: we have the answers to the questions that have been stopping you from pulling the plug on your next vacation.

We understand the journey, the ups, and the downs. We’ve been through the training, made our fair share of mistakes, and learned valuable lessons from them. This is what makes us the perfect people to assist you.

From thoughtfully crafted itineraries to having direct access to your dedicated Travel Professional, our mission is to remove the stress from your vacation planning. With our simple 3-step process, we’re here to help you every step of the way, ensuring that your dream destination becomes an unforgettable reality. is not authorized or endorsed by, or officially connected with The Walt Disney Company, or any of their affiliates. For official Disney information, visit

Hawaii Destination Specialist

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