There’s something special about experiencing the world through your grandchild’s eyes, whether it’s watching them marvel at the ocean for the first time or sharing stories over gelato in a quiet piazza. Retirement gives you the gift of time, and for many, the financial flexibility to turn those once-distant dreams into reality. Many of my clients come to me wondering how to weave family travel into their retirement plans, and it’s one of the most rewarding parts of my work. That’s because when your money supports the life you want to live, it becomes more than a plan—it becomes a legacy. If multigenerational travel is part of your vision, here’s how to bring it to life.

Why Multigenerational Travel Is Worth It

Multigenerational travel isn’t just a getaway; it’s an investment in your family’s story. Sharing new experiences across generations builds lasting memories and deepens bonds in a way that day-to-day life often can’t.

For many retirees, these trips are a chance to pass down more than just family traditions—they’re a way to share values like curiosity, gratitude, and togetherness. And while it’s easy to focus on the logistics or price tag, the real return is emotional: laughter around a dinner table in a new city, inside jokes from shared adventures, and the joy of simply being together.

Research from the National Library of Medicine backs this up. Social connection and meaningful travel can boost your health, mood, and mental sharpness in retirement.

In short, these experiences can be as good for you as they are meaningful for your loved ones.

5 Practical Ways to Structure Multigenerational Trips

There’s no one-size-fits-all approach to planning multigenerational travel. The best structure depends on your intentions, your budget, and what feels most meaningful—and manageable—for your family.

Here are a few thoughtful ways to design a trip that works for everyone:

#1: Treat the Entire Family

Treating the entire family to a vacation is a generous way to celebrate togetherness and create lasting memories. This often means covering major costs like airfare, lodging, and sometimes meals or activities to ease the financial burden on your kids and grandkids.

One key benefit is simpler logistics—you can choose the destination, set the schedule, and make decisions that align with your vision. It also makes it easier for everyone to say yes.

That said, be mindful of your retirement budget. Costs can add up quickly, especially during peak seasons or for large groups. Set a clear budget and communicate what’s covered to avoid surprises.

It’s also helpful to manage expectations. Treating the family is a wonderful gift, but framing it as a one-time opportunity—not a recurring obligation—helps keep it special and sustainable.

#2: Subsidize Key Expenses

If covering the full cost isn’t feasible or doesn’t feel quite right, you might choose to subsidize key expenses like airfare, accommodations, or a group activity. This approach offers meaningful support while keeping your own financial outlay more manageable.

The benefit here is balance. You’re helping ease the cost for your children and grandchildren without taking on the full responsibility. It also allows for shared ownership of the trip, which can foster appreciation and collaboration.

To avoid confusion, it’s important to clearly communicate what you’re offering to cover. Whether it’s a flat amount or specific items, setting expectations early ensures everyone is on the same page.

#3: Split Costs

Splitting costs with your children is a collaborative approach that can work well when everyone is in a position to contribute. It creates a sense of shared investment and encourages joint decision-making around travel plans.

The main advantage is that it distributes the financial responsibility, making the trip feel like a team effort. It can also open the door to more frequent or flexible travel, since no one person is footing the entire bill.

However, this approach also requires clear communication and coordination. Be sure to discuss budgets, expectations, and who’s covering what to avoid misunderstandings or stress leading up to the trip.

Finally, keep in mind that not all families are financially aligned, so flexibility and empathy go a long way.

#4: Gift an Experience

Gifting a trip can be a meaningful way to celebrate a holiday, graduation, anniversary, or other milestone. Instead of giving material items, you’re offering something far more lasting—quality time and shared memories.

The beauty of this approach is its thoughtfulness. It allows you to be intentional with your generosity while tying the travel experience to a special occasion. For families who value time together over “things,” it can be especially impactful.

If you’re considering this option, it’s still important to plan within your financial comfort zone. Depending on your estate plan, gifting travel may also have potential tax or legacy planning implications—something to review with your financial planner.

#5: Rotate One-on-One Trips

Rotating one-on-one trips with each grandchild can be a heartfelt way to create deeper, more personal connections. These smaller adventures give you the chance to focus entirely on one child at a time without the distractions of a larger group.

This approach allows for flexibility in both scheduling and budgeting. You can space the trips out over several years and tailor each one to the child’s interests and age, making the experience feel truly special.

The key is to plan with consistency in mind. If you start the tradition with one grandchild, you’ll likely want to continue it with the others. Budgeting ahead and setting expectations early can help ensure the experience is joyful for everyone—now and in the future.

Financial Planning Considerations

Incorporating multigenerational travel into your retirement plan is a meaningful way to align your financial resources with what matters most—connection, legacy, and shared experiences. Like any important goal, it’s most effective when thoughtfully integrated into your long-term strategy.

If family travel is part of your vision, here are a few key planning considerations:

• Build it into your budget. Create a dedicated “Family Travel” line item that reflects how often you’d like to take trips—annually, every few years, or tied to specific milestones. A bucket strategy can help you determine how much discretionary spending is available without compromising your long-term financial security.
• Understand the tax implications. If you’re gifting travel, be mindful of the annual gift tax exclusion ($19,000 per recipient in 2025). Some families use trusts or 529 plans to fund educational travel, particularly when the trips are cultural or academic in nature.
• Maximize travel rewards. Credit card points, airline miles, and hotel programs can help reduce costs or add special touches to the experience.

Lastly, consider the legacy you’re creating. Funding purposeful experiences now can be just as impactful as leaving money behind later. Whether through ethical wills or charitable travel, you have the opportunity to pass down not just wealth, but values and memories that last.

Planning Your Multigenerational Travel Itinerary

Planning travel for a large, multigenerational group can feel like a logistical juggling act, but it doesn’t have to be stressful. With the right resources and a little support, you can focus more on the fun and less on the coordination.

Here are a few companies that specialize in multigenerational family travel and can help bring your vision to life:

• Tauck Bridges. Known for their family-friendly itineraries in Europe, the U.S., and beyond, Tauck Bridges offers all-inclusive guided trips designed to engage travelers of every age, with activities that balance fun, learning, and cultural immersion.
• Road Scholar. Road Scholar’s intergenerational programs pair grandparents and grandchildren for educational adventures, from wildlife safaris to U.S. national park tours, with a focus on learning and connection.
• Adventures by Disney. These group trips offer Disney’s signature level of service and storytelling with a cultural twist—think VIP access, expert guides, and family-friendly accommodations around the world.

With the right partner, you can turn planning into part of the fun and ensure everyone has a trip to remember.

Multigenerational Travel and Your Retirement Plan

Multigenerational travel is one of the most rewarding ways to spend your retirement years—creating meaningful memories, deepening family bonds, and passing down your values through shared experiences. But like any worthwhile goal, it takes thoughtful planning to do it well.

At Align Financial, we specialize in helping clients align their money with the life they want to live. If multigenerational travel is part of your retirement vision, we’ll work with you to create a plan that brings it to life without compromising your future goals. Reach out today to see if we’re the right fit, and take the first step toward the meaningful, memorable retirement you’ve imagined.