Should You DIY or Work with a Travel Advisor?

A Guide for Busy Parents

Let’s be honest—planning a family vacation sounds fun in theory… until you realize it means juggling school calendars, navigating flight options, decoding hotel reviews, and Googling “best things to do in [insert destination]” at 11:30 p.m. with way too many browser tabs open.

As a mom of three and a luxury travel advisor, I’ve been on both sides of that screen. And while I fully believe that travel planning can be exciting, I also know how quickly it can go from fun to frustrating—especially when you're the one holding it all together at home.

So, should you plan your next family trip on your own? Or is it time to bring in a little help?

Let’s talk it through.

The Hidden Cost of “I’ll Just Figure It Out”

Trying to plan a vacation while juggling everything else? We’ve all been there.

There’s a common misconception that planning a trip is just a few clicks—book a flight, grab a hotel, done. But if you’ve ever tried to plan a vacation while managing everyday life (hello, soccer practice and school lunches), you know it’s rarely that simple.

DIY travel planning often comes with:

  • Endless research rabbit holes

  • Decision fatigue from too many “best-of” lists

  • Uncertainty about whether you're booking the right thing

  • And the lingering fear that you’re missing something important (like transfer times, visa requirements, or a better deal)

By the time you finalize the itinerary, you’re exhausted—and you haven’t even packed yet.

What a Travel Advisor Actually Does

Planning online is tempting—but having a guide makes all the difference.

When you work with a travel advisor, you’re not just outsourcing your bookings. You’re getting a professional guide, advocate, and trip designer.

I help families by:

  • Narrowing down realistic options based on your budget, travel style, and goals

  • Designing custom itineraries with built-in breathing room

  • Booking trusted partners and experiences that match your vibe (not just what looks good online)

  • Handling logistics you don’t even know to worry about

  • Being available if something goes sideways while you're traveling

Basically? You get to skip the stress and keep the fun. For more ideas on how to make your next trip go smoothly, check out these family travel tips for keeping everyone happy.

When DIY Might Make Sense

When your vacation feels like a breath of fresh air—and the planning was just as smooth.

To be fair, there are times when planning it yourself can work:

  • A simple road trip or weekend away

  • You have points to use and know exactly what you want

  • You genuinely love the research and have time to dive in

But for anything involving flights, international travel, multiple stops, kids’ needs, or high expectations? That’s where I come in.

How to Decide What’s Right for Your Next Trip

The vacation you dreamed of… without the planning stress.

Ask yourself:

  • Do I actually have time to plan this well?

  • Am I trying to accommodate different ages or travel styles?

  • Would I rather be on vacation than worrying about it?

  • If something goes wrong during the trip, who do I want to be on the phone with—customer service or someone who knows me?

Let’s Take Something Off Your Plate

Travel days are better when someone else handles the logistics.

There’s no trophy for planning the whole thing alone. (Though if there were, moms everywhere would deserve it.) My job is to make your travel experience smoother, more thoughtful, and a whole lot more fun—for you and for your family.

If you’re ready to enjoy the trip and the planning process, I’d love to help. You can download my vacation planning guide to get started!

Book your complimentary Custom Vacation Planning Session now by using my online scheduler to find a convenient time for you!

Let’s make this your most memorable (and least stressful) vacation yet.

Laura Legg

Hello, I’m Laura, the proud owner of Castaway Destinations, a boutique, full-service travel agency. As a busy mom of three, I understand the challenges of planning the perfect vacation. My dedicated team and I specialize in creating bespoke luxury trips across Europe and the Caribbean.

We leverage our extensive travel experience and destination knowledge to provide exceptional, personalized service tailored to your unique needs. Together, we make travel seamless and stress-free. Let’s turn your dream trip into a reality!

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