For years, a grand European train tour was on my bucket list. I never had the time to take a months-long trip, or, as a young adult, backpack and stay at hostels using trains as the main means of transportation. What I wanted was something more refined: a strategically plotted, multi-city affair taking in some of the world's most beautiful destinations from the comfort of a high-speed train.
I spent countless hours reviewing popular routes, but they all seemed to be missing one or two essential stops. I started plotting my own custom itinerary, determined to connect at least two places we had always wanted to visit. If you have dreamed of planning your own trip to Europe, check out my post, How to Plan Your Unique European Vacation. There I walk you through how I plan, and have links to each step in the process.
In 2016, that dream was finally realized, not through a knowledgeable tour operator, but through DIY dedication. This was a tight ten-day adventure stopping in five very different and unique cities across four countries. Our guide was a combination of detailed railway maps, an Excel sheet tracking expenses and options, and a fire burning inside.
After weeks of cross-referencing flights and rail systems, our first major hurdle became the backdrop: the cheapest transatlantic ticket landed us in Amsterdam (AMS), over 1,000 miles from our planned starting point, Venice. This single logistical choice—flying into Amsterdam and immediately taking a regional flight to Milan—became the essential framework for our entire MILAN → VENICE → VIENNA → COLOGNE → AMSTERDAM rail tour. This is how we brought the dream to life, and this is how you can too.
The Blueprint: Solving the Logistics Puzzle
The Amsterdam Hook: Strategy and Savings
This trip introduced us to a strategy we now rely on: leveraging the fastest and cheapest flights into a major European hub (like Amsterdam) and immediately pivoting to our real destination via a budget regional flight. In our case, that hub was Amsterdam.
While many sites (including Google Flights) now offer broad search tools, I relied on Kayak's Explore feature for initial research. I continue to use Kayak as a primary trip planner and repository because their service is amazing: you can simply forward confirmation emails, and they automatically build your entire itinerary, which you can then manually edit or update.
There are not many non-stop flights from Seattle to Europe. However, Seattle, being a major Delta hub, does have direct flights to Amsterdam (AMS) in just under 10 hours. Amsterdam is a massive European transit point, servicing cities all across the continent with inexpensive regional options.
Using Kayak Explore again, we snagged a one-way ticket to Milan on easyJet for about $80.00 each. The result was a significant payoff: instead of spending 5–6 hours waiting for a more expensive flight to Venice, we were in Milan—our rail tour launchpad—in just an hour and 45 minutes, ready to start the adventure.
Mapping the Stops: Building Our Ten-Day Flow
As this was first time seeing Europe by rail, we wanted to make the most of it and prioritize cities neither of us had experienced before. Our goal was to create a strategic sequence of stops to maximize sightseeing and ensure our return to Amsterdam by our deadline: to overlap with Mauricio's brother's trip.
1. Milan to Venice: The Quick Pivot
We started in Milan primarily because it offered the cheapest and fastest regional flight connection from Amsterdam, placing us in close proximity to our target. The high-speed train to Venice, a dream destination for both of us and the first of our new-to-us cities, takes only about 2.5 hours. This quick initial leg allowed us to dive straight into sightseeing without wasting a critical travel day.
2. Venice to Vienna: The Eastward Push
I had always longed to visit Vienna, drawn by its history and music. Since Vienna is on the far eastern edge of Austria, this stop was strategically placed as our longest single train journey. By scheduling this major travel day early, we moved to the furthest point of the itinerary, ensuring the remainder of the trip would flow naturally westward and be easier to manage.
3. Vienna to Cologne: The Timed Corridor and Scenic Detour
The time constraint was centered here: we needed to be near Amsterdam by Day 8 to overlap with his brother’s schedule. Leaving Vienna on Day 6 of 10 gave us two nights before the final leg. I opted to stop in Cologne because the journey allowed for a breathtaking scenic detour along the Rhine River Valley—a much-anticipated experience that required us to divert from only high-speed trains. Cologne's location then placed us just three hours from Amsterdam on the high-speed ICE train.
This sequence—pushing east, maximizing a scenic experience, and flowing naturally back to our flight hub—ensured that every day was purposeful and precisely on schedule.
Pass vs. Point-to-Point: The Financial and Logistical Calculation
Whether to buy a rail pass or purchase tickets individually was one of the major decisions of this trip. I conducted a lot of research on the pros and cons of both options, and we ultimately opted to buy point-to-point tickets. Here is why:
The Rail Pass Hurdle
The 2016 European rail pass options did not align with our trip requirements:
- Continuous travel for 15 days up to 3 months (Too long). A 15-day pass started at €476 per person.
- Travel for 4–7 days in one month (Did not fit our September/October dates).
- Travel for 10–15 days in two months (The only fitting scenario, but passes started at €447 per person).
Critically, with a pass, you are still required to go to the rail company and reserve seats where mandatory, which is an additional cost. For example, Frecciarossa high-speed trains require mandatory seat reservations, which are automatically included with a regular ticket from Trenitalia. When you ride with a pass, you must go through a third party like RailEurope and pay anywhere from €6 to €45 per seat. At an average of say, €20 per person per leg times four legs, that would add about €160 on top of the pass cost.
The Point-to-Point Advantage
I have read that unless you plan to travel extensively over several weeks, the rail pass is usually not the best deal. For our four essential journeys, we paid a total of $364.00, about €315. This is significantly less than any two of the cheapest passes available at the time.
| Ticketing Option | Base Cost (Per Person) | Mandatory Reservations (Estimate) |
|---|---|---|
| Cheapest Fitting Rail Pass | Starts at €447 | Add ±€80 |
| Our Point-to-Point Tickets | ±€157 | Included |
While a newer and cheaper pass is now available (starting at €283) that would have met our requirements, I would still choose to buy individual tickets. For a short, highly structured trip like ours, the certainty of booking months ahead was invaluable. I had no anxiety about whether the train we needed would be sold out and derail our itinerary—a very real possibility during peak season. We recently experienced this when we wanted to take a spontaneous trip to Segovia from Madrid, only to find that all high-speed morning trains except one were fully booked!
When a Rail Pass Does Make Sense
For someone who wants the flexibility of not booking a specific journey in advance, the rail pass can be a good option. For example, if I were renting a place for a month in central Italy, it might be nice to have that freedom to travel whenever I felt like it. For trips that prioritize efficiency and specific train times, the guarantee of a reserved seat that comes with a pre-booked individual ticket is worth more than the pass's potential flexibility.
Mastering the Stations: Navigating Europe's Hubs
I can totally understand why traveling this way can be intimidating for first-timers. It certainly was for me! When I look back at the itinerary, I am amazed it all went according to plan. At times during long-haul rail travel, it is often necessary to change trains. For example, a high-speed route might necessitate a change at a major hub, such as changing in Córdoba when traveling from Madrid to Seville. It's common to switch to a different national carrier (like swapping ÖBB for DB) or a different line at a border or regional hub (like Salzburg or Munich). This is why having your tickets and platforms confirmed in advance is so critical for smooth changes. I wasn't fully aware of the nuance of these connections when I planned this trip. Luckily, the initial legs of our tour minimized changes:
Milano Centrale and Venezia Santa Lucia:
Milano Centrale was our first experience at a major rail hub. I had spent many nights reviewing maps of all the stations we would be traveling through, so I felt fairly certain we would find our train with no trouble. By far, the most complex part of that first journey, that I had not bargained on, was locating the metro station that would take us to the train. Once we were there, it was simple to locate our platform, because the station has clear signage. We traveled from Milano Centrale to Venezia Santa Lucia easily and directly on the high-speed train. A critical lesson here: Patience is Key. In Italy, track numbers (Binario) are intentionally delayed until 10–15 minutes before departure to prevent platform crowding.
Wien Hauptbahnhof: Because there are only two direct trains from Venice to Vienna daily, the Austrian rail company ÖBB makes the journey into Wien Hauptbahnhof directly with no change required. This was a welcome simplicity for one of our longest legs.
The Complex Connection (Vienna → Cologne): Traveling from Wien Hauptbahnhof to Cologne, however, required two intermediate changes: one at Salzburg Hbf and one at München Hbf. I was glad I had studied the station maps prior to the trip. Salzburg has nine platforms, which puts it on the smaller end of stations. Munich, though, has 32 platforms, so it was crucial that I was sure where we needed to be to make that connection.
Helpful Hint: Understanding Local Transit. Although signage often is, don't expect all information to be in English. Familiarize yourself with the native words for the local train and subway systems. For example, the initials for a local transit company (like Milan’s ATM) could be confused with a bank machine by English speakers. It's important to know what the local commuter trains are called, like CercanÃas in Spain, so you are not watching the wrong departure board.
Core Takeaway: When navigating these complex transfers, your first and only priority is locating the large, central departure board upon arrival.
By the time of our final journey from Köln Hbf to Amsterdam Centraal, we were more than comfortable navigating the complex European train system.
Next Stop: Execution
After months of planning, the hard work was complete. We had leveraged the cheapest flights into Amsterdam, solidified a strategic route, and confirmed that point-to-point tickets offered the best value and certainty for our timeline. The research was done, the tickets were secured, and the hotels were booked. Finally, the bags were packed, which was our final logistical hurdle (you can read why I Only Travel with a Carry-on, and this trip is a perfect example why).
Join us in Post 2, as we board our first high-speed train, leaving the financial hub of Milan and heading toward the unique spectacle of the Grand Canal. We'll detail the high-speed experience and the sensory shock of arriving in Venice.
→ Read Post 2: High-Speed Italy: From Milano Centrale to the Grand Canal!
Thanks for stopping by and sharing!