How to Work With Me: An Insider Look at My Travel Planning Process

From whiskey trails to wine regions, here’s what actually happens when you book with Extended Escapes… and why it’s nothing like what you’d expect.

Let me tell you about the kind of traveler I work with.

They’re smart, busy, and they’ve been meaning to plan that trip for somewhere between six months and three years. They have a vision… maybe it involves a Scottish distillery or a sunrise over the Normandy coast… but every time they sit down to plan it, they end up with forty-seven browser tabs, a Reddit thread full of conflicting opinions, and the creeping suspicion that they’re doing this wrong.

Then they find me. And we fix that.

I’m Stephanie Austin, travel advisor and founder of Extended Escapes. I plan custom trips for people who love to travel but have zero interest in becoming amateur travel agents in their spare time. My specialty is the sip-worthy, soul-satisfying kind of travel… whiskey and wine adventures, WWII history in Normandy, Christmas markets, river cruises… the trips that feel personal rather than packaged.

Here’s exactly how working with me goes.

First, We Talk. Actually Talk.

Most people assume the planning process starts when they reach out. It actually starts the moment you land on this blog, read a post, and think “yes, that’s the kind of trip I want.” That moment of recognition… that’s already us getting to know each other.

When you do reach out, the first thing we do is talk. Not fill out an exhaustive form. Not answer a questionnaire. Talk. A complimentary 45-minute consultation where I ask you a lot of questions… and not just the obvious ones.

Q: What kinds of questions?

The destination questions come later. First I want to know how you travel. Have you navigated international trains and airports before, or does the idea of a connection in Frankfurt make you sweat? Do you thrive when the day is loosely structured and you can wander, or do you want to know exactly where you’re eating on Thursday night? Have you ever stayed somewhere that felt so right you didn’t want to leave… and if so, what was it?

Your travel history tells me more than any destination wishlist. It tells me your pace, your comfort zone, your version of a perfect day. And that’s what I’m actually building.

Case in point: a pair of women came to me with one thing on their list. A concert in Barcelona. That was it. What they left with was a beachfront hotel room upgraded to an ocean view, a bottle of sparkling wine waiting on arrival, and a trip that kept going from there. Cliff diving in Costa Brava. Skydiving outside the city. A London layover that turned into a full Harry Potter tour. They came to me with a ticket. They left with a trip they’ll be talking about for years.

Where and When (The Fun Part)

Once I understand how you travel, we dig into where and when. Destinations, obviously… but also timing, which most people underestimate completely.

Are we going peak season, when everything is buzzing but nothing is quiet? Shoulder season, when the weather’s still good and the crowds have thinned? Or that off-season sweet spot when the locals finally have time to pour you a proper drink and tell you the real stories?

We also talk about pacing… the thing that makes or breaks a trip and that most people get wrong when they plan themselves. Some travelers love the momentum of moving every two or three days, collecting hotel keycards like souvenirs. Others want to unpack once, settle into a home base, and actually feel like they live somewhere for a week. Neither is right or wrong. But mixing up the two styles on the same trip is a recipe for a vacation you need a vacation to recover from.

Q: So what happens after the consultation?

By the end of our call, we’ve nailed down the big three: timing, destinations, and a wish list of experiences. That’s where I take over.

I work with a network of travel partners… vetted, trusted people who know where the real experiences live. Not the TripAdvisor top ten. The family-run distillery that doesn’t advertise. The guide who knew your grandfather’s regiment. The vineyard dinner that never makes it into a guidebook. I connect those dots into a custom itinerary built around your wish list, and everything lives in a client portal so you’re never digging through email chains trying to find your hotel confirmation at 11pm in a foreign airport.

Traveling through Madrid

Why This Isn’t Just Booking Flights

There’s a planning fee to get started… between $150 and $300 depending on the scope of your trip. It exists because good planning takes real time, real expertise, and real investment in getting your trip right before a single booking is made. What you’re buying isn’t a document. It’s someone who’s genuinely in your corner from the first conversation to the last flight home.

Here’s what that actually looks like in practice:

Insider access. I know which experiences are worth the price and which ones are just pretty Instagram backdrops with a markup. More importantly, I know the people who can get you into the ones that never show up online at all.

Time. Planning a complex international trip properly takes dozens of hours. That’s time you’re spending at your actual job, with your actual family, living your actual life. Hand it to me.

On-the-ground support. When something goes sideways… delayed flight, closed distillery, weather that rewrites the itinerary… you’re not alone with a phone number for a call center. I track your trip and my partner network has people on the ground who can pivot fast.

The stuff you didn’t know to ask for. Room upgrades. Priority tastings. A private tour before the crowds arrive. Small surprises that make a trip feel like it was designed for you specifically… because it was.

Sometimes the most valuable thing I do isn’t glamorous at all. One client was getting her family to a wedding in rural Bavaria… and the German rail system had other ideas. Rather than leave her wrestling with Deutsche Bahn’s booking platform in a language she didn’t speak, I put together a custom video walking her through exactly how to search routes, pick departure times, and get everyone on the right train. Not a landmark moment. Not a rare bottle of single malt waiting at check-in. Just a problem that needed solving so her trip didn’t fall apart before it started.

Who I Work Best With (And Who I Probably Don’t)

I’m not the right advisor for everyone, and I’d rather tell you that upfront than waste your time.

I work best with busy professionals who want to explore the world… domestically and internationally… but don’t have the bandwidth to manage the details themselves. People who care about the quality of what’s in their glass as much as the view from their window. People who want their trips to feel curated, not cookie-cutter, and who understand that the best travel experiences don’t happen by accident.

I have a particular soft spot for travelers chasing whiskey and wine experiences… distillery tours in Scotland, vineyard stays in Bordeaux, bourbon trails in Kentucky, Calvados in Normandy after a day at the beaches. If you know what peated means and have opinions about it, we’re going to get along just fine.

If you’re looking for the cheapest deal on a package tour or a rock-bottom cruise price, I’m genuinely not your person… and I’ll tell you that rather than try to fit you into something that won’t work. But if you’re craving a trip that blends culture, flavor, and a little brag-worthy sophistication? Pull up a chair.

Q: What does working with a travel advisor actually cost… and when does the fee kick in?

The initial consultation is always free. No commitment, no obligation. We talk, I get to know your travel style, and you get a clearer sense of what your trip could look like. That part costs you nothing except 45 minutes.

If you decide you want to move forward, that’s when the planning fee comes in. It ranges from $150 to $300 depending on the complexity of your trip… how many destinations, how many travelers, how many moving pieces need to actually fit together. A long weekend in Napa is a different animal than coordinating a multi-country itinerary for a group. My fee reflects that.

What it covers: my research, the itinerary design, ongoing communication throughout the planning process, and access to my partner network… the people who make the good stuff happen. It also covers my support while you’re actually traveling, so if something shifts mid-trip you’re not left figuring it out alone.

The fee is collected after our consultation and before I start building your itinerary.

Once You’re On the Road

Think of me as your travel partner, not your travel babysitter. Once you’re traveling, I’m in the background… tracking flights, checking in periodically, available if something comes up. You’re a grown adult on vacation; the last thing you need is another notification.

What you do have is the peace of mind of knowing someone’s watching the logistics so you don’t have to. If your connection gets canceled, I know before you land. If something goes sideways with an excursion or a booking, my partner network has people on the ground who can pivot fast. The goal is for you to spend your trip actually in your trip… not managing it.

The Next Step Is Easy

If you’ve been sitting on a trip idea… one of those “someday” destinations that keeps getting pushed back because life is busy and planning feels overwhelming… this is your sign.

The consultation is free. The conversation is easy. And the worst case scenario is you hang up with a clearer sense of what your trip could look like, even if we don’t end up working together.

Because here’s the thing… you deserve more than a “nice little trip.”

Book your complimentary consultation here.

Want more on how I plan specific types of trips? Start with my Whiskey Travel Hub or Normandy Highlights Hub… both give you a sense of how I think about building a trip that actually means something.