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

From whiskey trails to wine regions, here’s what to expect when you book with Extended Escapes.

Planning a big trip feels like a full-time job…one that involves too many browser tabs, too many Reddit reviews, and too little time. That’s where I come in.

I design custom travel experiences for people who love exploring but don’t love the planning part. Think of me as your travel strategist, fixer, and logistics whisperer, especially if your idea of a good time involves a glass (or flight) of something worth sipping.

Ready to start planning your next escape? Schedule a complimentary consultation.

Here’s how it all works.

Q1: Your travel planning style clearly stands out from the typical “book-and-go” agent. What kind of experience should someone expect right from their first conversation?

A1: I ask a lot of questions…and not just about where you want to go. I want to understand how you like to travel. Have you navigated international airports and trains before? Do you thrive on exploring independently, or do you prefer a bit of structure and support? What kinds of hotels, villas, or boutique stays have felt right to you in the past? And maybe most importantly: what types of experiences have you loved… and which ones fell flat?

Your travel history tells me a lot. It helps me design an escape that is built just for you… not something pulled from a brochure or copy-pasted from the internet.

Q2: Once you’ve gotten to know a client’s travel style, what happens next? How do you start shaping an itinerary or experience around that?

A2: Then we dig into the fun part: where and when. We talk about destinations, of course, but also timing… are we planning for peak season energy, shoulder-season balance, or that off-season sweet spot when the crowds thin and the locals have time to chat?

We’ll also cover pacing. Some travelers love the adventure of packing and unpacking every few days, collecting hotel keycards like souvenirs. Others prefer to unpack once and settle into a home base. Neither is right or wrong, it’s all about finding your rhythm.

Traveling through Madrid

Q3: You clearly put a lot of thought into the travel planning process. How do you turn all that conversation into a finished trip? What does your process look like from first chat to boarding pass?

A3: By the end of our consultation, we’ve nailed down the big three: timing, destinations, and a wish list of sights and experiences. That’s where I take over the logistics.

I work with my network of trusted travel partners, the ones who know the best drivers, guides, wineries, distilleries, and boutique stays, to build a custom itinerary around your wish list.

Every detail lives in my secure client portal, so you can access your flights, hotel details, transfers, and day-by-day plans in one place. No spreadsheets, no digging through emails. Just your trip, organized and ready.

Q4: How do you choose which tours, tastings, or experiences to recommend?

A4: This is where the customization really comes in. I’m not handing you a list of generic “Top 10 Things to Do.” I curate experiences that match you… your pace, your interests, your comfort level.

If you love immersive, local travel, that might mean a cooking class in Lyon or a private WWII history walk in Normandy. If you’re the type who likes your itinerary with a pour, I’ll connect you to small-production distilleries or vineyard dinners that never make it onto TripAdvisor.

And if you’re the kind of traveler who wants to stay active, I’ve got options for that too: cycling through Tuscan vineyards, hiking the Scottish Highlands, or golfing in New Zealand. Prefer a slower pace? No problem. We can lean into scenic drives, long lunches, beach lounging, and spa days between tastings.

Every trip has its own tempo; I customize your trip to make sure it matches yours. I like to balance the mix: some structured experiences, some free time, and maybe a wildcard or two…something that nudges you just enough outside your comfort zone to make your story even better.

Q5: That sounds very streamlined. So once the itinerary is finalized, how involved are you while the client is actually traveling?

A5: Think of me as your travel partner, not your helicopter parent. I’m here when you need me, not hovering when you don’t.

I track your flights and do periodic check-ins to make sure things are running smoothly. Between me and my regional travel partner network, you’ve got logistics support on the ground if things go sideways: delayed flights, weather hiccups, missed connections, all of it.

You don’t need to spend your vacation time troubleshooting. That’s my job.

Q6: For someone new to working with a travel advisor, what kind of investment should they expect,  both in terms of your planning fee and the value they get in return?

A6: I don’t charge a planning fee. My value comes from the time, expertise, and connections I bring to the table.

Here’s what you actually get when you work with me:

• Insider access. Vetted travel partners around the world who know where the real experiences live…not just the ones on Instagram.

• Time savings. I handle the logistics, bookings, and coordination so you can focus on enjoying your trip instead of managing it.

• On-the-ground support. If something shifts mid-trip, my partners and I handle the pivot.

• VIP touches. Upgrades, priority tastings, private tours, and surprises that make your trip feel personal.

• Peace of mind. You handle the sipping, sightseeing, and story-making. I’ll handle the details that keeps everything running smoothly behind the scenes.

Q7: What types of travelers do you work best with? Who’s your ideal client — and who might not be the right fit?

A7: I work best with busy professionals who want to explore the world, both domestically and internationally, but don’t have time to handle the planning details themselves. My clients are people who value their time, appreciate good food and drink, and want trips that feel curated, not cookie-cutter.

I have a special passion for travelers chasing whiskey and wine experiences: distillery tours in Scotland, vineyard stays in France, bourbon trails in Kentucky, and everything in between.

If you’re looking for a deal on a Carnival cruise or a rock-bottom all-inclusive spring break vibe, I’m probably not your person. But if you’re craving a trip that blends culture, flavor, and a little brag-worthy sophistication, we’ll get along just fine.

➡️If you’re curious about how I plan whiskey-focused trips, check out my resource: The 4 Whiskey Personalities Guide.

Q8: If someone’s reading this and thinking, “Okay, this sounds like me,” what’s the best way to get started?

A8: I make this easy…reach out to set up your complimentary consultation.

Whether you’re dreaming of sipping your way through Scotland, chasing vineyard views in Bordeaux, or just taking a much-needed break that actually feels like one, this is where the process starts.

➡️You deserve more than a “nice little trip.” Let’s make it the kind of journey your friends secretly wish they’d booked first.