Planning a Multi-Generational Family Vacation

Kimmie Moehring, CFP® CDFA®
Aug 10, 2023 4:15:00 PM

A family vacation sounds great, right? Until someone has to make a decision that affects everyone on the trip.

Being in the decision-making seat can be very stressful when you know that different things make different people happy, and another layer of complexity is added when planning activities for a wide range of age groups.

Where do you start? I just planned a family vacation, which included my parents (grandma and grandpa), my brother and his wife, and their two girls (ages 3 and 5), and it sparked much discussion. As a group, we needed to agree on where to go, how to get there, what to eat, what to do, and for how long. With the vacation now completed, I wanted to share some of the takeaways from our experience, specifically for a vacation with multiple families and generations.


“It’s so great to have found that special person to make the daily decision of what we’re having for dinner for the rest of our lives!” This sentiment was in a recent anniversary card my dad had given my mom on their 45th anniversary. Married or not, we can all relate to the “what’s for dinner?” dilemma. As a perpetual reality for all of our lives, it’s a daily decision we as adults make. Some might perk up at the thought of making delicious, gourmet cuisine, while others dread the inevitable decision. The goal for our vacation? Avoid that daily decision – three times per day for nine days—our solution: family Disney cruise.

We chose a cruise because of all the activities, entertainment, and excursion options. An all-inclusive could have the same impact on the meal situation, but we also wanted to be sure everyone, from the littlest to the most experienced traveler of the group, would be entertained. It was worth the extra cost for our family as it allowed everyone to be more relaxed and avoid anyone getting too “hangry.”

Where to Go?

Determining a place where no one has “home field advantage” allows everyone to get out of their routine and unwind from reality. Consider if there are any bucket list destinations for the family. Maybe someone has an idea that would be unique. We wanted to do something no one had done together so that we were all experiencing something new. If you are taking off on a cruise, please plan to arrive at your port of departure area the day before the cruise departs. I know too many travelers who didn’t get to their cruise because of delayed or canceled flights and insufficient wiggle room for another option.

What to do?

Knowing travelers' ages and physical abilities to do various activities would benefit any trip planner. Catering to both ends of the spectrum is hard to balance, but getting feedback from the group on what type of activities people are interested in, how many activities to do in a day, and how much downtime everyone needs are all important factors. For example, in our family of 5 adults and two small chuldren, we knew we would want to have a lot of family time but also some adult time. Did you know Disney has an “It’s a Small World Nursery” on all their ships? From playtime, to nap time to bedtime, they are open. Your little ones can stay on their nap schedule while the older ones play or go down to bed earlier as the adults enjoy a later night together. This service was one of the best values on the ship and allowed everyone to have a great time!

We also decided that the girls operate best when they have breaks from big activities, so we only had one activity per day and planned for “free days” to be spontaneous. My wise brother recognized the reality of the level of energy and time it takes with their little ones to transition from event to event,  and it created a good cadence of events. Each traveler also added what was on their vacation wish list, and each person’s activity was considered. Everyone was able to do what was on their list!  Every family will be different, so I just share with worked for us.

Financing the Trip

Of course, we, as financial planners, want you to plan your finances so you are not putting it on a credit card with an 18% interest rate. You can be creative with your vacations and find something that fits your budget. But most importantly, the sooner you plan the trip, the sooner you can start saving. Or better yet, you create a “travel fund” now, and start contributing to that monthly, so when you are ready to go, you already have a running start on your financing!


Even with all the planning, things don’t always go as planned. Two of our three excursions were canceled (and thankfully, refunded!) due to unsafe wind conditions, and we had rain for half of the days. Weather will always be out of our control, but because of all the great things to do on the boat, we had a great time and made the most of it. Communication before the trip and determining a plan/itinerary helps make the experience as best for all! Despite the weather, we would all do it again in a heartbeat. 

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