How to Plan a Trip to Europe for the First Time

Most Americans fly across the Atlantic, spend thousands on a Europe trip, and come back feeling like they missed something.

You probably did. Not because you went to the wrong places. Because nobody told you how Europe works before you got on the plane.

I’m Kris. I started Hidden Jam after one too many trips where the “luxury group experience” turned out to be strangers awkwardly sharing a van to a hotel that looked nothing like the photos. At some point, I stopped booking those trips and started building better ones. Now I take people sailing the Amalfi Coast, Croatia, and Greece. I’ve traveled to 80+ countries, I’m a licensed boat captain, and I’ve made most of the mistakes described below at least once. Here’s what I’d tell you before you book.

Should You Visit Multiple Countries on Your First Trip to Europe?

The short answer is no. And I’ll tell you why people always try anyway.

You travel such a long distance, and your brain says: maximize everything. Six countries in three weeks feels logical. What usually happens is you spend more time in transit than in any of these countries. Every city starts to blur into the next. You come home exhausted, having technically seen a lot and experienced none of it.

My personal advice is: don’t do multiple regions within the same country either. Northern and Southern Italy are two different worlds.

In a nutshell, choose one place and go deep. I know that feels wasteful when you’ve just crossed an ocean, but it’s the only version of this trip you’ll want to repeat.