How I Plan Trips to Europe (Without Overpaying for Flights)
My Travel Toolkit: How I Actually Plan My Trips to Europe
For a long time, I thought travel to Europe had to be complicated.
Expensive flights. Rigid plans. Months of research.
But over the years—and after a lot of trial and error—I realized something much simpler:
I don’t need a perfect plan.
I just need a few reliable tools—and a flexible mindset.
This is the exact “toolkit” I use every time I plan a trip.
It Always Starts With the Flight
I don’t start with a destination.
I start with a deal.
If I see a great flight—especially something around $550 roundtrip from the East Coast, or a rare business class fare—I pay attention.
That becomes the starting point.
From there, everything else begins to take shape.
I Think of Europe as Connected
One of the biggest shifts for me was realizing:
Europe isn’t a single destination—it’s a network.
I think of routes like New York or Philadelphia to London or Rome as the “Uber routes” of Europe.
They run constantly, pricing is competitive, and they open the door to everything else.
Once I land, I can take a train or a short flight almost anywhere.
That’s when the trip really begins.
I Let the Trip Evolve
I don’t map everything out in advance anymore.
I’ll:
fly into one city
take a train to another
adjust based on what feels interesting
Sometimes the best parts of a trip are the ones I didn’t plan at all.
Where I Stay Matters More Than I Thought
Over time, I’ve learned that where I stay shapes the entire experience.
I look for places that are:
centrally located
walkable
connected to the rhythm of the city
I want to step outside and feel like I’m in it—not just visiting.
I Travel Smarter (Not Harder)
I don’t obsess over points, but I do use them intentionally.
I use travel-friendly credit cards for everyday purchases, take advantage of promotions when they come up, and apply points when it makes sense.
It adds up over time—sometimes in ways that make a trip feel much more accessible.
Timing Makes a Difference
I’ve found that small shifts can completely change pricing.
Flying midweek.
Staying a little longer.
Being flexible by even a day or two.
Those decisions open up options most people never see.
The Toolkit Behind It All
None of this happens by accident.
It’s a simple system I’ve refined over time—tools I use to:
find flights
compare options
choose where to stay
move between cities
If you’re curious, I’ve put everything I use in one place:
Free downloadable Travel Blueprint here
Once You Find the Flight…
That’s when the real magic begins.
If you’re heading to Portugal, I’ve created a curated Lisbon experience—including a self-guided adventure—to help you explore the city in a more meaningful (and fun) way.
👉 Explore the Lisbon Experience →
~Jen
The Travel Speakeasy
