Multigenerational Family Vacation Planning: How to Create Meaningful Travel Experiences for Every Generation
Study after study has found that spending money on experiences yields far greater rewards than spending on material possessions. Imagine how rewarding it will feel to plan a multigenerational family vacation that creates lasting memories and improves the return on life (ROL) for multiple generations of your loved ones.
When stepping into a new chapter of life—perhaps after a loss, divorce, or becoming an empty nester—planning a multigenerational family vacation can be especially meaningful. Planning a multigenerational experience allows you to celebrate resilience, reconnect with loved ones, and create new traditions. You don’t need to have all the answers or carry the whole load yourself. Just opening the conversation can lead to something beautiful.
Of course, getting everyone on the same page will be no small feat. Hopefully, the challenge of arranging all the details will be part of the fun, as coordination will be difficult with so many people involved. If you’re wondering how to plan a multigenerational family vacation that honors everyone’s preferences, this checklist will help you get started.
1. Open the dialogue.
Tagging along on someone else’s vacation can ruin the trip for everyone. No one wants to feel pressured to take off work, spend money they don’t want to spend, or go somewhere they’re not really interested in.
One of the most crucial steps in multigenerational family vacation planning is opening the dialogue early. A successful trip requires navigating the varying stages of life and responsibilities across generations. Grandma and Grandpa might have nothing but free time, while younger family members may be juggling school, sports, and work schedules. That’s why family travel planning across generations requires clear communication and shared flexibility.
Even if, as the organizer and main benefactor, you have some ideas or destinations in mind, try not to preplan your big family vacation. Use video chat, a shared Google Doc, or your next family gathering to initiate a dialogue with everyone you’re inviting. Let every member of the family voice their ideas about where to go and what to do. Start a group calendar so everyone can share their availability and schedule. Once you have some common ground, it will be easier to get everyone there at the same time.
2. Balance shared activities with alone time.
When planning a vacation for a large group of people, it’s essential to strike the right balance between spending time together and having time apart. Not everyone has the same hobbies, skills, or interests. And even activities that a large part of your family are excited to do might exclude young children, older seniors, and their caregivers.
And that’s okay—provided that your schedule and your destination are both flexible. Let the golfers schedule a tee time while the musical fans take in a show. Drop the teenagers off at a theme park so their parents can have a spa day. If one family wants to cash in their frequent flier miles at a five-star hotel, the Airbnb enthusiasts can stay at a nearby condo. As different families and generations take their own paths through the trip, your loved ones might feel like following each other on a new adventure or discover that those cousins they only see every other year also share a love for museums.
One time when we were vacationing in Florence, my wife, one of my sons, and my daughter wanted to go shopping along the Ponte Vecchio. My other son had no interest in shopping. I pulled out my phone and found what appeared to be a nice hike. He and I went hiking while the others were shopping. It was one of my favorite parts of the trip. We hiked above the center of Florence and had a fantastic view.
Give everyone a little room to do their own thing, and anchor your vacation around activities that everyone can enjoy together, such as spending time at the beach or meeting up for dinner.
Remember, this kind of trip is about more than money. It’s also about how you choose to spend your TEAM of resources—Time, Energy, Attention, and Money—with the people who matter most. By giving everyone the freedom to explore in their own way while also carving out moments of connection, you’re investing in shared joy and deeper relationships.
A thoughtful, multigenerational family vacation strikes a balance between structure and freedom, creating moments for both connection and personal fulfillment.
3. Set and stick to a budget.
Nothing can kill the mood in a room—or on a plane—faster than money talk among family members.
When budgeting for a big family trip, it’s important to consider everyone’s comfort zone and plan accordingly. Avoid choosing a destination that will significantly impact anyone’s budget solely due to airfare costs. Select a locale that offers something for everyone. Families who want to spend more on amenities and experiences will have the flexibility to do so during their “me time” without making more frugal vacationers feel like they must break the bank.
Whether you’re funding the entire trip or coordinating group expenses, multigenerational family vacation planning requires a clear understanding of everyone’s comfort zones when it comes to spending.
And if you’re generously cracking open your nest egg to fund a once-in-a-lifetime family vacation by yourself?
Then budgeting is even more important. If you don’t set some limits, your goodwill might get the best of you—and your money.
4. Take Your Age and Health Into Consideration.
When planning a trip that spans multiple generations, it’s also important to consider each person’s age, health, and life stage, including your own. If your dream vacation involves more physical activity or travel logistics, consider taking it while you’re still able to enjoy it fully. Waiting too long may mean missing out on the energy or mobility that would make the experience more enjoyable.
This doesn’t mean rushing or pressuring yourself, but rather honoring your current capacity and choosing joy in the present moment. I explore this idea further in my blog post, “Bucket List Planning: Align Your Health With Your Goals.”
5. Closing Thoughts.
If you’re considering a big family trip—and especially if you’re navigating a new phase of life—it’s worth taking a step back to see how this experience fits into your broader picture. Let’s discuss how to align this trip with your values, relationships, and financial goals. Together, we can ensure that your Life-Centered Financial Plan supports both the memories you want to make and the life you want to live.
Schedule a call, and let’s start the conversation.
This Week’s Favorite Reads
This week’s favorite reads include articles discussing financial decluttering and building better money habits, ways to avoid replacing old products, a guide to essential estate planning documents, the productivity paradox, and some benefits of working longer.
Here are the links to this week’s articles, as well as a brief description of each and why you should check it out:
1. Build Better Money Habits: 10 Financial Things You’ll Never Regret Throwing Away.
When it comes to decluttering, we often focus on clearing out our closets and getting rid of things we no longer use or want. However, we can also declutter our financial lives. Performing this task can help us build better money habits. This article suggests 10 financial things you won’t regret getting rid of. Several of these items jumped out at me. For example, according to a survey cited in the article, consumers have an average of 3.3 subscriptions they don’t even use. The average cost? $32.84 per month, or close to $400 annually. If you take the family trip referred to above, you could use that money towards a nice dinner for everyone.
2. Getting Bored With Your Old Products? You Don’t Have to Replace Them.
Do you often get bored with what you have and feel compelled to buy new stuff? Could there be a better way? We find new products and experiences exciting. They bring us joy. On the other hand, old ones fall out of favor. The result? We want something new. Acting in this way gets expensive. It’s also not environmentally friendly. What would happen if we chose to change the accessories that go with the things we own? The article suggests that changing a superficial feature can make a difference. For example, consider buying a new case for your phone that reflects current trends or your interests. The article suggests that “finding happiness with material goods isn’t solely about acquiring more; it’s about deriving joy from what we already own.
3. An Expert’s Guide to the Estate Planning Documents Everyone Needs.
Creating a financial plan—or even better, a life plan—can help you achieve a sense of financial security and peace of mind. But what happens if you die suddenly, or can no longer manage your affairs due to incapacity? These events can unexpectedly happen to anyone, which is why you need an estate plan. Estate plans ensure that the people to whom you want to pass your wealth receive the assets in the right way. You also want to plan for your incapacity. As a result, your estate plan should include a financial power of attorney, a healthcare power of attorney, and a living will. In short, you want to have the right team in place to carry out your wishes when you are no longer here. Check out the article to learn more.
4. The Productivity Paradox.
Can doing less make you more successful? Often, as soon as we wake up, we start going through our mental to-do list. We keep working, pushing through exhaustion. For many, caffeine, willpower, and the fear of falling behind keep them pushing through. We praise those who hustle and keep going. However, the article suggests that behavior could be holding us back instead. After all, our brains are not built for constant output. We need to take at least the occasional break. Studies show that cognitive performance declines dramatically after 90 minutes of focused work. We end up with decision fatigue, mental fog, and burnout. This behavior can lead to a drop-off in performance. Read the article for some suggestions on how to address this issue.
5. Why Women May Want to Work Longer: It’s About More Than Money.
Many older workers are choosing to retire later. As stated in the article, there are many potential causes for this. The rise of remote work and the impact of financial stress sit near the top of the list. Changes in England’s retirement laws have increased the amount of time women remain in the workforce there. Researchers studied these women and discovered that “women who continue to work beyond age 60 have, on average, significantly better cognition and fewer signs of physical disability than had they retired at age 60.” Those working in physically demanding jobs found a health boost. On the other hand, those working in sedentary jobs saw a decline in their health. To learn more and understand why, check out the article.
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