There is nothing in the world that I love more than having all of the people I love the most in one place. I love to travel and I love to share my new experiences with my family…and I mean my WHOLE family. But it is not easy planning for so many people with so many interests. There are some common mistakes I see many people make when plnanning a multigenerational vacation. If you want to have the best multigenerational vacation just follow these tips… and don’t try to please everyone!

I am currently planning a trip that includes my parents, my brothers (I have 3!!) with their significant others, my husband’s parents, and my sister-in-law and her boyfriend – with my husband and my daughter that is 14 people total. I am so excited to spend my daughter’s first birthday with everyone in the Most Magical Place on Earth…of course I am going to Walt Disney World 😉 but the insight I am sharing here applies to all destinations. Here are some common pitfalls to avoid when planning a trip for multigenerational travelers, whether your group is 14 people or 4. 

Not Including Everyone in the Planning 

If you are reading this you are probably (like me) the designated planner of the group. Whether you enjoy the planning and coordinating (again, like me) or it was thrust upon you, it is super important to get everyone involved in the planning. Even if they push off the responsibility onto you and insist they don’t care what you do – they care! It happens all the time: someone who doesn’t care and doesn’t want to be involved in the planning is the first to complain when they don’t like something or they missed something they would like to do. I have a rule that everyone MUST pick the one thing that they want to do while we are at their destination. 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.

Trying to Do Too Much 

Building off of the last tip, it is important to not try to plan too much beyond those “one things” you got in the previous step, especially if you are traveling with little ones. I like to plan 3 things per day, one in the morning, one in the afternoon, and one in the evening. If everyone is feeling great and ready to keep going, we do more, but anything extra we fit in is a bonus. I hate wasting time trying to figure out what to do, so what I do when I plan my three things is have a list of other possibilities that make sense based on where we will be. You can give the group those few choices and be on your way. And it is important to build in downtime. Planning with a spread of ages means you will have varying levels of stamina. Keeping the kids on their nap schedule, or building in a morning to sit and drink some coffee and chat in a cafe will help minimize the meltdowns from children and adults alike. When we travel even my husband needs his nap!! 

Spending Every Single Moment Together 

The more people you have, the more interests, diverse personalities, travel styles and possibilities to push each other’s buttons. It is ok to split up, especially if somebody’s one thing is worse than going to the dentist for someone else. My brother Michael and I have similar travel styles, interests, and love going places together. I still need a little bit of a break from him and his need to stop and share life stories with EVERY SINGLE person we encounter. My brother Greg and I, on the other hand, are on complete opposite ends of the planning spectrum. He doesn’t like to plan in advance, he doesn’t like to get up early to beat the crowds, yet he would rather skip something than wait for it. When we travel together I create a plan, tell him where we will be and when, and leave it up to him if he is going to join us or not. If I spend a whole week nonstop with my family it will end with me in tears. Over the years I have learned it is ok to take breaks from each other. It makes it so much fun to reconnect over dinner and hear about what everyone experienced that day. 

Not planning far enough in advance 

When you are dealing with travel arrangements for more than a few people, everything gets a little more complicated. Dealing with schedules can be difficult. In most cases you are dealing with a small window where everyone is available, and the more people you add the more your dates become less and less flexible. This is extremely important when booking accommodations and you need multiple rooms. If you are considering a villa style accommodation, those usually book months and months in advance, so book early to ensure that you are able to get what you want. Most resorts have flexible cancellation policies, so it is always better to book more than what you need if you think more people may be joining you. 

Going To The same place year after year 

I see this all the time: you take your first vacation with your kids and enjoy it, so you book the same destination again the following year, and the year after that. You know you will like it, you know the kids will like it, why take a risk? But if this is the only way you vacation, you are missing so many amazing destinations and cultural experiences. Just because you have kids does not mean you are restricted to only vacationing at a theme park or the all inclusive restaurant with kids clubs. Don’t underestimate your kids. 

Not Talking About $$ 

I know it is always the most awkward topic, and it is the biggest mistake I made when planning my first trip with my parents and in-laws. Not having the conversation about budget at the beginning stage of the travel planning makes it more and more difficult as you go. There are two ways to approach the conversation – if it was your vacation, and as you talked about it family members jumped in, lay out the costs. Consider as much as you can, including food, gratuities, and transportation. “We would love if you would join us, the cost is going to be x.” If you are going into the vacation intending it to be a trip you can all enjoy together, talk about the budget. I like to do this with individuals before coming together as a group to talk destinations and experiences, so no one feels embarrassed if their budget isn’t as high as others. Then find a destination that works for everyone! I also like to discuss things like who will be paying for meals and drinks if you are not at an all inclusive location – this helps avoids fights over the check or your card declining if you were expecting to split meals and everyone looked to you when the bill arrived. The earlier you have this conversation, the less awkward and stressful it will be. 

Doing it yourself 

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. Whoever takes on the bulk of the planning also takes the responsibility for everyone having a good time. Coordinating arrival times for different cities or transportation to your excursions can become a full time job. You already have two full time jobs (I am a Mom too, I know!) and you don’t need the added burden of worrying about everyone else. That is why there are people like me to help. I am a Family Travel Advisor and I specialize in planning multi-generational trips, so I think of all the things you may not have. I get paid a commission that is built into the cost of your vacation by the supplier – they either keep it or they pay me, so my services are no additional cost to you. 

There’s no right or wrong when it comes to choosing a destination, there’s only what works for your family. Beach vacations, ski vacations, cruises, theme parks, and even dude ranches can make great multigenerational trips if you plan wisely. Before the trip, consider all travelers’ interests, bucket list dreams, travel style, travel comfort, and travel budget. 

If you are ready to start planning your next adventure but not sure where that should be check out some of my favorite destinations for multigenerational families.

 

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