Ready to escape rigid travel packages and organized tours? Now that you've checked the advance planning essentials, here are the first two critical steps to nailing down your itinerary.
Step One
Snagging Cheap Flights
Kayak Explore — leave the destination blank
The trick is flexibility. Instead of picking a destination first, pick the price first. If you are locked into landing in one specific city on one specific day, you will pay a premium.
Start watching prices 3–4 months before your trip. Snag the cheapest flight to anywhere on the continent. Once you are in Europe, getting around via train or budget airline is cheap and easy.
- Example: For a recent fall trip, I aimed for Central Europe. I found tickets to Milan for half the price of Barcelona or Paris, and a third of the price to Germany. Milan became our entry point — saving us hundreds of dollars per person — and the start of what became our Second European Rail Odyssey.
- Tools I Use: Kayak's Explore feature lets you put in your home airport and leave the destination blank to see a map of the cheapest places to land. Google Flights has a similar function.
Step Two
Deciding on Your Initial Destination
Mérida, Spain — not the most famous, absolutely worth it
Once you land, you have a choice: do you stay in that arrival city, or immediately jump to another one?
The first time I took a train around Europe, we flew into Amsterdam because it was the cheapest flight from Seattle. We didn't stay there — we immediately hopped on a budget flight to Milan for about $70 to start our real journey. You can read all about that trip in The Inaugural European Rail Odyssey.
Be careful with budget European airlines like Ryanair, Vueling, or EasyJet. The carry-on allowed for free on your major transatlantic flight will likely cost you a checked bag fee on a European discount airline. Their size limits are often stricter than US carriers.
We learned this the hard way — we paid an extra $50 because Mauricio had a backpack and a carry-on suitcase.
My workaround: I now travel with a collapsible backpack. I roll it up and keep it inside my main suitcase for that specific flight segment to avoid the extra fee.
The Full Guide
Thanks for stopping by and sharing!