158. Stop Trusting Google With Your Biggest Trips | Luxury Travel to Your Dream Destinations

You can Google a hotel. You can ask AI for an itinerary. But what happens when flights get canceled, ports change, or the trip you planned online starts falling apart? In this episode, I’m pulling back the curtain on what really happens behind the scenes of seamless luxury travel to your dream destinations, and why having a professional in your corner matters most when the unexpected hits. You'll learn what Google and AI tools miss about rooms, neighborhoods, and timing, the behind the scenes moves that prevent small issues from becoming trip-ruining stress, and how to spot the kind of specialist travel advisor who protects your time, your money, and the moments you can’t get back.

Previous Episodes Mentioned:

• 129. Celebrating Latin America — Insider Travel Tips, Cultural Stories & Luxury Adventures
• 134. Master Holiday Travel Without Being a Karen

Connect with Michele on IG: @jetsettingwithmichele or on Facebook: www.facebook.com/groups/MMTinsiders

Contact Michele to plan your next vacation: www.makinmemoriestravel.co/contact

This episode was produced by The Podcast Teacher: www.ThePodcastTeacher.com. 

Transcript

158. Travel Advisor Appreciation Month: The People Behind Your Perfect Trip

Welcome back to another episode of Jet Setting with Me. It's me, Michele, your friendly wanderlust instigator.

May is a lot of things. It's the official start of peak travel season. It's Mother's Day, graduation weekends, and the month when half of my clients suddenly realize they need a Europe itinerary for July. But there's one thing May is that doesn't get nearly enough airtime—and that's Travel Advisor Appreciation Month.

Now, yes. I realize I might be a little biased. But I want you to stay with me here, because this episode isn't really about celebrating my industry. It's about giving you a window into what actually happens behind the scenes of every trip that goes beautifully right—and what protects you when things go sideways.

And in my experience? That story almost never gets told.

I remember sitting on my couch watching the very first season of Survivor and thinking — genuinely thinking — why would anyone voluntarily do that? Eating bugs, sleeping in the rain, getting voted off by people you were supposed to trust? No, thank you. I was fine right where I was.

But then The Amazing Race premiered, and something completely different happened. The minute those teams started sprinting through airports and navigating cobblestone streets and opening clues in places I'd never even seen on a map, I leaned forward and said out loud — how do I audition for this?

That was about twenty years ago. I was in my late thirties, I had seen almost every corner of the United States — I take that seriously, by the way; I've been to all 50 states and I have a rule that leaving the airport doesn't count unless you actually explore something — but I had never once set foot outside of North America. And something about watching those teams race through the world cracked something open in me. I didn't have a word for it yet. I just knew I wanted more of whatever that feeling was.

Wanderlust. I learned the word later. But The Amazing Race gave me the feeling first.

The Google Problem

Let's start with the thing I hear most often, usually said with the best intentions: "I can just look it up on Google."

And yes—you can. I'm not going to pretend the internet isn't a treasure trove of travel content. It absolutely is. But here's what Google can't do: Google has never sat in that particular villa in the Amalfi Coast and noticed that the rooms on the left side face the road while the ones on the right open to a view that will genuinely make you emotional. Google doesn't know that a certain highly rated hotel has been undergoing a soft renovation, and the "standard" rooms are currently backed up to the construction zone. And Google definitely doesn't pick up the phone at midnight on a Sunday when your connection gets canceled, and you're stranded in an airport in a country where you don't speak the language.

There's the trip you can build from a browser tab—and then there's the trip that's been designed by someone who has done the homework, walked the floors, tasted the food, and built relationships with the people who run the places. Those two trips are not the same trip.

What travel advisors bring isn't information. You have information. What we bring is knowledge—the kind that comes from years of experience, industry training, supplier relationships, and, honestly, from being travelers ourselves. There's a difference between reading about a place and knowing a place. And that difference shows up in every detail of a well-crafted itinerary.

I had a client reach out recently who was extending her stay in Paris after her son's school trip wrapped up. The school had its accommodations sorted, but she wanted something more befitting a grown woman who has earned her Paris moment — which, same.

She didn't need me to Google "hotels in Paris." She needed me to know Paris. And I did, because I was just there in March.

I put together a proposal with three options, all properties I had personally visited or stayed in. The first was the smart choice — the best value of the three, genuinely lovely, no compromises. The second was the splurge: a view of the Louvre that makes you understand, in a single glance, why people build their entire trips around this city. And the third was near the Champs-Élysées, which on paper sounds like every tourist itinerary ever written — but when you have two pre-teen kids in tow and you want them to feel the magic of Paris without a spreadsheet itinerary, there is nothing like putting them on that boulevard and watching their eyes go wide.

She couldn't have gotten that proposal from a search engine. She got it because her travel advisor had just walked those streets two months earlier and knew exactly which room, which neighborhood, which tradeoff was right for her family. That's the difference.

What We Actually Do

I want to walk you through what a travel advisor actually does, because I think it would surprise you.

Before I start planning anything, I spend a significant amount of time getting to know the traveler. Not just where they want to go, but how they travel. Are they early risers who want to be first in line at the museum, or do they prefer a slow morning with good coffee and a view? Do they want every dinner pre-booked or some spontaneity built in? Is this a trip to celebrate something—and if so, what does that celebration mean to them? Have there been any trips that didn't feel quite right, and what was off about them?

Those conversations are where the real planning begins. Because a trip to Paris for a couple celebrating their 30th anniversary is a completely different trip from Paris for a mother and daughter doing a long weekend of museums and shopping—even if the hotels are on the same block.

From there, the work is layered. We research. We reach out to our supplier partners. We check on availability and negotiate when we can. We build an itinerary that flows—that doesn't have you racing from one side of the city to the other or arriving at a property during a local holiday when everything is closed. We review the fine print. We brief our clients before they leave so there are no surprises. And we stay accessible throughout, because travel, as beautiful as it is, does not always go according to plan.

And here is what I want you to hold onto: none of that is something you'd see on a brochure or a booking site. It happens quietly, in the background, before your trip ever begins.

Let me give you a real example of what that behind-the-scenes care actually looks like in practice.

In 2025, I had the privilege of coordinating a group sailing for the Matchmaker Alliance Association aboard Virgin Voyages' Scarlet Lady—nearly 100 sailors, there for a full schedule of meetings and events on the water. It was a beautiful trip, and the kind of group program that requires lots of moving parts to stay aligned.

On the last day of the meetings, the group coordinator I worked with on board pulled me aside with a heads-up: rough seas were coming. Nothing dangerous, but enough to be felt—and on the final day of a professional conference, the last thing anyone needs is to be caught off guard by a queasy stomach mid-session.

So I did what any good advisor does when they have information that can help: I used it. I pulled up WhatsApp and sent a message to the entire group, right then, while there was still time. The message was simple—if anyone was prone to motion sickness, take your medication now, before the seas pick up. Because here's the thing most people don't know: by the time you feel like you need it, it's already too late for it to take effect.

Attendees reached out specifically to say they appreciated it—that it was exactly the kind of thoughtful touch that made the difference between finishing the conference on a high note and spending the afternoon horizontal in their cabin.

That's what this work is. Not just the itinerary. The awareness, the relationships on the ground, and the willingness to act on information the moment you have it.

The Safety Net

Let's talk about disruptions. Because they happen.

Weather delays. Airline cancellations. Hotel overbookings. A strike that shuts down transportation in a major city on the day your clients are supposed to be transferring to the airport. Political unrest that shifts a destination from recommended to inadvisable overnight. A medical emergency overseas.

I don't say any of this to alarm you—the vast majority of trips go smoothly. But travel is, at its core, an exercise in navigating the unknown. And when something does go wrong, the difference between having a travel advisor and not having one is enormous.

When you've booked everything yourself through a mix of apps and airline websites and hotel booking platforms, you are managing each of those relationships individually. Which means that when the flight is canceled, you're in a hold queue. When the hotel has a problem, you're navigating that on your own. And you're doing all of that while you're jet-lagged, possibly in a different time zone, maybe with children or elderly parents in tow.

When you have a travel advisor, you have one point of contact who knows your entire trip—every piece of it—and has the relationships and the tools to move quickly. That's not a small thing.

And I'll give you a real example—one that hit close to home, or rather, close to my Facebook feed.

I have a friend. She's someone I adore, but she has a well-established habit of wanting to "pick my brain" rather than actually work with me. No judgment—I know I'm not alone in this experience. Travel advisors everywhere are nodding right now.

When Spirit Airlines filed for bankruptcy, she reached out. Should she book future travel with them? And I was honest with her, the way I'm always honest: I told her I actually love Spirit's premium seating product. For the right trip, it's a genuinely superior option to what Southwest was offering. But—and this was a significant but—I told her in no uncertain terms that I would not book Spirit for my own travel while they were in bankruptcy proceedings. The uncertainty alone makes it a risk not worth taking.

She didn't take my advice.

I know this because a few weeks later, I saw it on Facebook. She missed traveling home for Mother's Day. Not because of a freak storm or an act of God—because the airline she'd been warned about couldn't hold it together long enough to get her there.

That one stung a little, if I'm being honest. Not because I needed to be right, but because that was a Mother's Day she doesn't get back. And that's exactly the kind of thing a travel advisor exists to protect you from—not just the logistics, but the moments that matter.

The Emotional Weight of This Work

Here's the part I don't think gets talked about enough.

Travel advisors don't just plan trips. We hold people's most meaningful moments. A couple's first international trip after years of wanting to go but never quite making it happen. A milestone birthday that a family has been saving toward for a decade. A solo journey someone is finally taking after a divorce or a loss—rediscovering who they are outside of a role they've been playing for years.

People hand us their dreams, which is a responsibility I find genuinely humbling. It's also what makes this work deeply personal rather than transactional. I'm not moving reservations around on a screen. I'm helping someone create a chapter of their life.

I've had clients cry—happily—when they sent me photos from a trip. I've had people come back and say, "That was the trip that changed everything for us." That feedback doesn't get old. Not even a little bit.

If I'm being honest, the trip that changed me most wasn't the most glamorous one I've ever taken. It was Costa Rica. Specifically, it was climbing Mt. Arenal — an active volcano — which was so far outside my comfort zone that I'm still a little surprised I said yes.

I talk about that journey in full in episode 129 — the link will be in the show notes if you want the whole story — but what I'll tell you here is this: the moment I started descending that volcano and realized I had actually done it, I burst into tears. Not delicate, photogenic tears. Full, ugly, relief-and-happiness tears. Because I had asked something hard of myself and I had shown up for it.

That's what travel does, when you let it. It shows you what you're made of in ways that no boardroom, no comfort zone, no carefully controlled environment ever could. And that feeling — that specific combination of terror and triumph — is exactly why I do this work. I want that for my clients. Every single one of them.

The Evolution of the Travel Advisor

There's a narrative that's been circulating since roughly the invention of Expedia that the travel advisor is a relic—a profession made irrelevant by technology. I'd like to put that narrative to rest, not because I'm defensive about it, but because the numbers simply don't support it.

According to the American Society of Travel Advisors, the use of travel advisors has been growing, particularly post-pandemic. Travelers who experienced the chaos of the COVID era—the cancellations, the refund nightmares, the uncertainty—came out of it with a clear understanding that having a professional in their corner is not a luxury. It's a strategy.

The role has also evolved. Today's travel advisors are specialists. They're not order-takers on the phone flipping through a catalog. The best advisors have deep expertise in specific niches: luxury travel, adventure travel, Disney, river cruises, Africa safaris, multigenerational trips, accessible travel, and culinary experiences. That specialization is exactly what makes us valuable—because depth of knowledge produces a better trip than a general search ever could.

And the relationship between advisors and their clients has shifted, too. The best partnerships I have are ongoing. I know my repeat clients the way a great stylist knows their client's wardrobe—what works, what doesn't, what they're ready to try next. That continuity is built over time, and it produces something that no algorithm can replicate.

How to Find and Work With a Travel Advisor

If you don't currently work with a travel advisor, here's my honest advice on finding the right one.

Look for a specialist, not a generalist. The best advisors have a lane—and they're very good in it. If you want a luxury African safari, find someone who does luxury African safaris. If you want a Disney trip, find a Disney specialist who has done the certification work and knows every corner of every park. Generalists can be fine for straightforward trips, but for anything meaningful or complex, depth matters.

Ask about their process before you talk about destinations. How do they get to know you as a traveler? What does their planning process look like? How do they handle disruptions? A great advisor will spend your first conversation asking more questions than they answer. If it feels like a pitch before they've learned anything about you, keep looking.

Pay attention to how they communicate. Are they responsive? Do they follow through? Do they explain things clearly without making you feel like you're being managed? The relationship has to feel right because you're trusting this person with something that matters to you.

And yes, great advisors often charge planning fees, and that is a feature, not a bug. When someone has skin in the game, you have their full attention. Free advice is worth exactly what you paid for it.

And while we're on the subject of being a great traveler—not just the logistics, but the full picture—a thoughtfully crafted itinerary is only as good as the mindset you bring to it. Travel is a shared experience, and how you show up matters. Pack your patience right alongside your passport. If you want a deeper dive into what that actually looks like in practice—especially when airports are running at full chaos, and everyone's nerves are stretched thin—I devoted a whole episode to it. Episode 134, Master Holiday Travel Without Being a Karen, covers everything from mindset to etiquette to the smart hacks that keep you gliding through the mayhem with your cool intact. The link is in the show notes, and honestly? It's worth a listen before any trip, not just during the holidays.

A Note on Appreciation

Travel Advisor Appreciation Month exists for a reason—and it's not because the industry lobbied for a Hallmark holiday. It exists because the work is largely invisible, and visibility matters.

If you have a travel advisor you love, reach out this month and tell them so. Not because they need the validation, but because the work of making something look effortless is still work—and the people who do it well deserve to know that it lands.

And if you don't have a travel advisor, and this conversation has planted a seed—I'd genuinely love to chat. You can find me on Instagram at @jetsettingwithmichele. DM me and let's talk about where you want to go and what you want to feel when you get there. That's always the best place to start.

Coming Up Next Week

Next week, we are celebrating something truly once-in-a-generation—America’s 250th birthday. The Semiquincentennial is on July 4th, 2026, and I have been looking forward to this episode for a while. We’ll talk about how to experience this milestone in a way that’s truly meaningful—from the grand celebrations in Philadelphia and Washington, D.C., to the quieter, more personal ways of marking the occasion across the country. Whether you’re planning something big or just want to understand what this anniversary really represents, you won’t want to miss it

Until next time, make every journey a memory worth savoring.