ABOUT me

The best parts of travel are the unplanned ones. The tiny places you wander into. The conversations you didn’t expect. The moment you look at each other and go, “This is it.”

I had that moment in Inverness on my honeymoon. A small local pub, a pint (or two), strangers who felt like friends by the end of the night. That is the kind of travel I want for you.

I design Europe trips for couples who want more than a checklist. Better pacing. Better choices. A trip that feels like you, with the details handled and room for the magic to happen.

my MISSION

Let’s plan the kind of Europe trip you’ll talk about for years.

Hi, I'm Jennifer Stilwell

Let’s be real. Planning a Europe trip can feel like you need a spreadsheet, three browser windows, and a minor in geography. Too many options, too many hot takes, and somehow you are still not sure if you picked the right place.

That’s where I come in.

I built Sassenach Travel Agency for couples who want Europe to feel romantic, easy, and worth the money. I take your wishlist and turn it into an itinerary that flows, with great hotels in the right spots and a pace that does not burn you out.

I’m the person who will tell you what’s actually worth booking, what you can skip, and how to avoid the “why did we do this to ourselves” version of Europe.

You deserve a trip that feels like you. I make sure it does.

ABOUT

Luxury travel advisor

Not all five-star hotels are created equal. Not all “must-do” lists are worth your time. And a trip can look amazing online and still feel wrong in real life. I make sure that doesn’t happen.

I plan Europe trips for couples who care about quality and want the trip to feel un-rushed and intentionally planned. The right neighborhoods. The right stays. A route that makes sense. And built-in breathing room so that you can actually enjoy it and each other.

You bring the wishlist. I’ll handle the decisions, the bookings, and the details you didn’t even know to think about. Because the goal is to come home feeling closer, not exhausted.

High-Touch, High-End Travel: That Actually Fits You

I plan Europe trips for couples who want it done right. I build the itinerary around your wishlist, handle the hotels and logistics, and stay in your corner before, during, and after you travel.

travel SERVICES

Hosted Europe Trip

This is my once-a-year escorted small group trip to Europe and it’s not the kind of trip you can recreate with a few TikToks and a spreadsheet. It’s built around what’s actually worth your time, with access and timing you’d never think to plan for.

What makes it even better is that our destination changes every year. One year it might be Scotland. Another year it might be Italy. Sometimes it’s a new country, sometimes it’s a specific region that deserves the spotlight.

This is the trip you build into your life. The one you look forward to all year. If you joined me every year, in 20 years you could have 20 places checked off your wishlist and a whole collection of stories you still bring up over dinner and drinks. The kind that turns into “remember when we…” year after year.

I plan the whole thing and I’m right there with you. Route, hotels, logistics, all handled by me. It’s paced well on purpose with fewer moves and more time to actually enjoy where we are. And yes, downtime is non-negotiable.

Whether you’re coming as a couple, solo, or with a friend, the group vibe is part of the magic, and spots are limited by design.

If you even think you might want to go, join the waitlist. That’s how you get first access to the destination and dates before it’s shared publicly.

One trip each year. Small group. I handle everything.

Ready to Plan Europe?

Schedule your complimentary consultation and
let’s build a trip that fits you.