Why Families Should Stop Waiting for the “Perfect” Time to Travel

Planning the Trip of a Lifetime—Without the Stress

Family travel often comes with a long list of challenges: school schedules, sports tournaments, fluctuating prices, and the constant question of when to book. Many families believe that waiting for a “better deal” or the right time will make things easier. The reality? The best trips are usually the ones planned early and rooted in purpose, not perfection.

Travel advisor Jill Benedict, who helps my family plan our vacations, has seen this play out countless times. She explains that families who book early often get the best prices—and better options. Cruise lines, resorts, and theme parks frequently offer price protection, meaning if rates drop before your final payment, you can adjust and save. Waiting for Black Friday or last-minute deals, on the other hand, can lead to paying more or missing out entirely.

When we look at travel through a financial lens, this advice holds up. Just like investing early can maximize long-term gains, booking early multiplies your opportunities—from cost savings to upgraded experiences.

Experience Over Everything

During our recent Mediterranean cruise, I saw firsthand how the right preparation can turn a trip into a lifetime memory. My wife and I spent a few days in Rome before boarding the ship, a decision that made all the difference. We weren’t rushing from one flight to another, trying to make up for lost time. Instead, we eased into the experience, explored the city, and created the kind of memories you can’t schedule.

Jill often reminds clients that a trip isn’t just a destination—it’s a sequence of experiences. Hiring a local guide, for example, gave us access to hidden corners of Rome, from small-town pasta lunches to lesser-known cathedrals. Those moments were just as meaningful as visiting the Colosseum or the Vatican.

When families think about travel only in terms of cost, they miss what really matters: shared time and connection. Experiences have a lasting emotional return that far outweighs the expense.

The Hidden Costs of Waiting

Families often hesitate to book trips early because they’re waiting for school and sports schedules to settle. Jill shared a story about a client who planned a milestone family trip to Hawaii months in advance. They booked early, secured a two-bedroom villa at a significant discount, and looked forward to celebrating a grandmother’s birthday together.

Then the call came: their son’s baseball tournament had been scheduled for the same week. Moving the trip meant losing a $6,500 discount. Suddenly, they faced a choice between a fleeting tournament and a once-in-a-lifetime family memory.

As a parent of four, I understand that struggle. My own daughter, Madison, made a swim team that qualified for a major competition—scheduled the same weekend as our family’s European trip. I never miss her meets, but this time I told her, “We’re getting on that plane.”

It wasn’t the Olympics, and missing one event wasn’t going to define her career. But our time together as a family—those experiences—will shape who she becomes. There are only so many summers left before our kids leave home.

You Can Do Most Things, But Not Everything

In my work with families at TAMMA Capital, I see this tension every day. Parents want to do it all: fund college, retire comfortably, support their kids’ passions, and still make room for meaningful family experiences. But life requires trade-offs.

I often tell families—and my wife, Teresa—“You can do most things in life, but you can’t do everything.” The families who find peace are the ones who define their priorities clearly. If experiences and connection matter most, then plan for them intentionally. Build them into your financial strategy the same way you plan for college or retirement.

When your purpose is clear, your decisions become easier. Whether that means saving monthly for a yearly trip or booking that cruise a year in advance, you’re aligning your spending with your values instead of reacting to whatever’s cheapest in the moment.

The Social Media Trap

Part of what drives the pressure around travel and family life is comparison. Instagram and TikTok are full of people showcasing perfect vacations, new cars, and elaborate lifestyles. What we don’t see are the financial realities behind those posts—credit card debt, loans, or even inheritance windfalls that make them possible.

As Jill pointed out, some families save for years to take a single dream trip, while others finance experiences they can’t really afford. From a financial planning perspective, neither choice is right or wrong. What matters is whether those decisions align with your goals.

Social media is a highlight reel, not a financial plan. Comparing your family’s story to someone else’s is a losing game. The real measure of wealth is freedom—the ability to spend time where it matters most.

How Many Summers Do You Have Left?

One of the most meaningful tools I’ve shared with families is something I call the Calendar of Memorable Moments. It’s a simple chart showing how many summers are left before your children leave for college. When parents see that number—five summers, three summers, maybe just one—it’s often emotional. It puts things in perspective.

When you look at time through that lens, suddenly the question shifts from “Can we afford this trip?” to “Can we afford not to take it?”

For my wife, Teresa, that visual hit hard when our triplets started high school. It was a reminder that the window for shared experiences is shrinking. We can always make more money, but we can’t make more time.

The Joy of Paying It Forward

There’s also a beautiful generational ripple effect that comes with family travel. Jill has seen an increasing number of adult children booking trips and inviting their parents along—sometimes even covering the cost as a way to say thank you.

These multi-generational experiences are about more than sightseeing. They’re about gratitude, legacy, and shared joy. Whether it’s grandparents taking their kids and grandkids on a Disney cruise or adult children treating their parents to a European trip, travel becomes a tangible expression of love and appreciation.

And for parents who still have kids at home, these experiences lay the foundation for something even more meaningful: raising children who want to come back and travel with you as adults.

Travel Is an Investment in Family

Families often think of travel as an expense, but I view it as an investment—one that compounds in emotional value. Years from now, your kids won’t remember the new sports gear, but they’ll remember snorkeling in Hawaii, exploring ancient ruins, or laughing together over a bad meal on a cruise ship.

The destination matters less than the shared experience. Whether your family’s trip is a modest road trip or an international cruise, the memories created together form the real return on investment.

When you plan early and spend intentionally, you give your family something that can’t be replicated—a sense of belonging, adventure, and connection that outlasts any season of busyness.

Forget Perfection

There’s no perfect time to travel, just as there’s no perfect financial plan. Both require intention, flexibility, and a clear sense of purpose. Whether you’re navigating a sports schedule, saving for college, or planning your next vacation, remember this:

You can do most things in life, but not everything. Choose the experiences that matter most—and start planning them today.