Multigenerational Travel: How to Plan a Trip With Your Grandkids in Retirement

The Trip Three Generations Actually Want to Take Together

If you've ever tried to plan a family vacation that works for a nine-year-old, a 45-year-old, and a 68-year-old, you know it isn't easy. But more retirees are figuring it out anyway. Multigenerational travel — grandparents, adult children, and grandkids all traveling together — has quietly become one of the biggest trends in the travel industry, and retirement is often what makes it possible. You finally have the time. The question is how to plan a trip everyone will actually enjoy, without blowing up your budget or your back.

Why This Is Having a Moment

This isn't just a feeling — the numbers back it up. In Road Scholar's 2026 Multigenerational Travel Survey, more than 57% of respondents said they'd already taken a multigenerational trip, and over half said they're actively considering one in the next year. Interestingly, the same survey found a real shift in priorities: respondents increasingly value shared memories and emotional connection over hitting bucket-list destinations, and nearly 76% said unique learning experiences matter as much as — or more than — just seeing a famous landmark.

In plain terms: your grandkids probably aren't dreaming about a hotel pool. They're dreaming about time with you.

Let Your Income Plan Do the Worrying, Not You

One quiet reason multigenerational trips get postponed year after year is money anxiety — not because the trip is unaffordable, but because it feels risky to spend from savings you're not sure will last. This is exactly where having a clear "retirement paycheck" changes the conversation. When your essential expenses are already covered by predictable income sources, a family trip becomes a line item in a plan instead of a gamble against your nest egg. You're not asking "can we afford this?" in a panic every time — you already know the answer, because your income plan already answered it.

If travel is a priority for you, it's worth building it into your retirement income conversation explicitly, rather than hoping there's "some left over" each year.

Choosing a Trip That Works for Every Age

The survey data points to a few patterns worth borrowing from:

• Built-in activities for every age. Nearly 38% of respondents ranked "activities for all ages" as the single most important factor in planning — more than destination itself.
• Nature and hands-on experiences win. Wildlife encounters and national park trips were the top choice for 44.8% of multigenerational travelers, likely because they naturally give everyone something to do at their own pace.
• All-inclusive simplifies everything. Almost 70% of respondents preferred an all-inclusive style trip that bundles lodging, meals, and activities — one less thing for anyone to coordinate or argue about.
• Shorter can be better. A 6-to-9-day trip was the sweet spot for over a third of respondents — long enough to feel like a real getaway, short enough that nobody runs out of patience.

The Practical Logistics Nobody Warns You About

A few planning habits go a long way toward keeping the trip about connection instead of chaos:

• Ask about mobility needs honestly. Nearly one in five survey respondents specifically cited accessibility for varying mobility levels as a top concern — don't assume everyone in the group moves, or wants to move, at the same pace.
• Build in downtime on purpose. Schedule at least one "nothing planned" day so young kids can nap and grandparents can rest without feeling like they're holding the group back.
• Talk about paying before you go, not during. Whether one family covers lodging and another covers activities, agree on the split ahead of time so money never becomes part of the trip.
• Loop in a travel advisor for bigger trips. For anything involving flights, multiple rooms, or international travel, a specialist who handles multigenerational trips can save real time and headaches.

The Takeaway

Multigenerational travel isn't a luxury add-on to retirement — for a lot of families, it's becoming one of the main reasons retirement matters. The families who make it happen year after year usually have one thing in common: they've already answered the money question ahead of time, so it never competes with the memory-making.

If you're not sure whether travel and other lifestyle goals actually fit into your current retirement income plan, that's a conversation worth having before you start booking flights. We're happy to walk through it with you — no pressure, just clarity.

Source: Road Scholar, "Multigenerational Travel Survey Insights for Families," 2026.