How to Know You’re Picking the Right Trip for Your Family (Without Second-Guessing Everything)

You’ve got 14 tabs open, three group chats with conflicting opinions, and a spreadsheet that’s starting to look more like a research project than a vacation plan.

It’s no wonder so many families get stuck in what I call “travel decision limbo”—so many amazing options, but no clear way to know which one is right.

Here’s the good news: there isn’t just one “perfect” trip out there. There’s the one that’s perfect for you.
And that’s exactly what I help my clients figure out.

The Truth: There’s No One-Size-Fits-All Vacation

It’s easy to get caught up in what everyone else is doing. Maybe your friends swear by their Hawaii trip, your sister loved her European cruise, and your coworkers can’t stop talking about Costa Rica.

They might all be right—but that doesn’t mean any of those trips are automatically right for you.

The best trip isn’t the trendiest or even the most luxurious—it’s the one that fits your family’s pace, personality, and priorities. The one where everyone gets what they need, without anyone feeling like they’re just “along for the ride.”

And when a destination is new or unfamiliar? That’s when the overwhelm really sets in. It’s hard to know where to start—so people do what feels easiest: they ask around. But when you crowdsource, you’ll get 100 different opinions… and none of them are built around you.

That’s where I come in. I help you quiet the noise, narrow the focus, and build a trip that feels like it was designed just for your family.

How to Tell If a Trip Is the Right Fit

When I’m helping clients choose where to go, these are the questions I always guide them through:

1️⃣ What’s your family’s energy level?

Are you happiest exploring from sunrise to sunset—or do you prefer a mix of adventure and downtime? Matching the pace of the trip to your family’s natural rhythm is the key to coming home refreshed, not exhausted.

2️⃣ What’s everyone excited about?

Kids, teens, grandparents—they all have their own version of fun. The right trip balances everyone’s interests so no one feels left out (and everyone gets a “that was my favorite day” moment).

3️⃣ When are you traveling—and what’s realistic for that time of year?

Timing can make or break a trip. I help clients choose destinations that shine in the season they’re traveling—whether that means avoiding crowds, finding better weather, or taking advantage of unique experiences that only happen at certain times.

4️⃣ How far outside your comfort zone do you want to go?

For some, adventure means ziplining through a rainforest. For others, it’s trying a new dish or navigating a local market. Knowing your family’s “adventure threshold” helps me recommend the right kind of experience—thrilling or gentle, but always fun.

5️⃣ How do you want to feel when you come home?

This is my favorite question. Do you want to feel energized and accomplished—or rested and reconnected? That answer tells me everything about the type of trip we should build.

How I Help My Clients Find Their Perfect Fit

Every family is different. That’s why I start with a conversation, not a checklist.

I listen for what lights you up—those offhand comments about “we love good food” or “the kids would lose their minds if we saw penguins.” Then I use that to guide everything from destination selection to resort choice and pacing.

I often work with families who know they want something different, but aren’t sure what that looks like. Maybe they’ve always done all-inclusives but want to try Europe or an Alaska cruise. Maybe they want something adventurous, but still comfortable.

I remind them there’s no right or wrong—just your trip. The one that fits your family’s interests, comfort level, and style. My job is to help you find the best options, simplify the process, and make the decisions easier so planning doesn’t feel like another full-time job.

“You made the whole process so easy. We didn’t just love the trip—we loved how much it fit us.”

That’s what I want every client to say when they get home.

Because You Deserve More Than Just a Vacation

You deserve the kind of trip that feels effortless, thoughtful, and exactly right for your family. The one that balances excitement with ease—and lets you actually be in the moment while you’re there.

That’s what happens when you stop second-guessing and start planning with someone who knows how to connect the dots between where you are, what you love, and how you want to feel.

Ready to find your perfect trip?

Let’s take the stress off your plate and build a vacation that fits your family—not someone else’s.