Planning a three-month trip through Europe can feel overwhelming at first. We definitely had moments where we asked ourselves, “Where do we even begin?” Looking back now, the process wasn’t nearly as intimidating as it seemed, it just required taking it one step at a time. 

Here’s exactly how we planned our trip from start to finish, along with what we learned and what we’d do differently if we were planning it again. 

Step 1: Dream First, Plan Later

Before we worried about flights, budgets, or transportation, we simply made a list of everywhere we wanted to go. Some countries had been on our bucket list for years, while others were places we’d heard incredible things about from friends and family. Once we had our initial list, we started asking everyone we knew who had traveled to Europe questions like:

“What was your favorite country?”

“Is there anywhere you’d skip?”

“What’s underrated?”

“Where should we spend more time?”

This helped us add destinations we hadn’t considered while also crossing a few off our list. 

Step 2: Let ChatGPT Help Build the Route

Once we had our dream destinations, we turned to one of our favorite planning tools, Chat GPT. Honestly, we used ChatGPT throughout almost our entire planning process and even while we were traveling. We gave it our list of countries and cities and asked it to create the most logical travel route. One thing we quickly learned is that the order of your trip matters just as much as the destinations themselves. 

Originally, our plan was to begin in Lisbon, Portugal and finish in Nice, France. But after thinking about the weather, we realized we’d be starting our trip in early April. Southern coastal destinations like Portugal and Spain would be much more enjoyable later in the spring. So, we completely flipped our itinerary.

Instead, we started in France and gradually worked our way around Europe to finish in Portugal. Looking back, that was one of the best decisions we made. Each destination seemed to get warmer as the trip went on, and we were able to enjoy beaches, outdoor cafes, and coastal towns during much nicer weather. 

Step 3: Decide How Long to Stay

Once our route was finalized, we went city by city. Again, ChatGPT became incredibly helpful. We asked questions like:

“How many days should we spend in Florence?”

“Is two days enough for Prague?”

“Is Cinque Terre worth three nights?”

“What’s the ideal amount of time for Barcelona?”

We also compared those recommendations with travel blogs, YouTube, and other travelers’ experiences. Overall, the recommendations were surprisingly accurate. 

What We’d Do Differently

If we could plan the trip again, we’d add one extra day to almost every city. 

When you’re constantly moving every few days, you don’t realize how exhausting travel days become. 

Packing

Checking

Getting to the station

Taking a 5hr train

Checking into the next hotel

Finding dinner

Suddenly, your “travel day” is your entire day.

That extra day would have given us time to relax, do laundry, sleep in, or simply enjoy the city without feeling like we had to be sightseeing every minute. 

Step 4: Pay Attention to Travel Time

This is probably our biggest piece of advice. Don’t just look at a map. Actually look at how long it takes to travel between destinations. Some cities that look close together still require:

Multiple train transfers

5-6 hours of travel

Early morning departures

Long walks between stations

Those long travel days often left us with very little time to explore our next destination. If we planned the trip again, we’d coordinate the number of nights in each city based on the travel time required to get there. Sometimes spending one extra night makes the entire trip much more enjoyable. 

Step 5: Organize Everything

Once we finalized our route, we entered everything into Polarsteps. This quickly became one of our favorite travel apps. Not only did it map our entire route visually, but it also let us document each destination with photos and journal entries that friends and family could follow in real time. 

One of our favorite features is that you can turn your trip into a professionally printed travel book after your journey. We ordered ours, and it’s something we’ll treasure forever. 

Step 6: Book Flights and Accommodations

Now it was time to start making everything official. Booking accommodations naturally locks you into an itinerary, but many hotels offer free cancellation until a few weeks before arrival. This ended up helping us several times. 

As our trip evolved, we cancelled a few reservations and extended our stay in places we unexpectedly fell in love with. 

We primarily booked through:

Booking.com

Hotels

Bed & Breakfasts

Airbnbs

Our priorities were simple:

Clean

Safe

Great location

Strong reviews

We aimed to spend around $100 per night total, or approximately $50 per person.

Hostels can certainly save money, but since this was our first extended backpacking trip, we preferred having our own private space. Booking 6-12 months in advance also helped us secure much better prices. 

One lesson learned the hard way? Always double-check your dates and location before confirming your reservation. Some bookings are completely non-refundable. 

Dividing Responsibilities

One thing that made planning much easier was dividing responsibilities. 

Ben became our hotel expert. He researched accommodations, compared reviews, and booked our stays. I focused almost entirely on transportation. Instead of both of us trying to plan everything, we each became responsible for one major piece of the trip. 

It made the planning process much less overwhelming. 

Step 7: Transportation

We knew early on that we didn’t want to rent a car. Driving in unfamiliar countries, dealing with parking, toll roads, and different driving laws wasn’t something we wanted to worry about. Thankfully, Europe has an incredible public transportation system. 

After weeks of research, we discovered Eurail. We purchased the 3-Month Unlimited First Class Global Pass. I’ll be honest… Learning Eurail wasn’t easy. At first it felt confusing. The reservations, passes, regional trains, high-speed trains, night trains etc. There was definitely a learning curve. But after enough research, everything finally clicked. 

I’ll write a separate article explaining exactly how Eurail works because it deserves an entire guide on its own. 

Step 8: Travel Essentials

Planning wasn’t just about booking transportation and hotels. We also researched everything we’d need to live abroad for three months. 

Some of the things we prepared included:

Travel health insurance

Passport copy left with family

Digital passport copies

eSIM phone plans

Packing strategies

Luggage choices

We ended up using Saily for our eSIM and had excellent service throughout Europe. We also purchased travel health insurance. No one ever asked to see proof, but having coverage gave us peace of mind. Luckily, we never needed it. 

Step 9: Keep Saving & Book Activities Later

Even after the major bookings were finished, we continued saving money each month leading up to the trip. One thing we intentionally didn’t do? Book every activity months in advance. 

Since we traveled during shoulder season, we found that many experiences (boat tours, cooking classes, museums, and wine tasting) still had plenty of availability, some even at a discount. Instead of locking ourselves into a rigid schedule, we usually booked excursions one to two weeks before, or even just a day or two in advance. That flexibility allowed us to adjust our plans based on weather, how we were feeling, and recommendations we received while traveling. 

Final Thoughts

Planning a three-month trip can be intimidating, but looking back, it all came together by taking one step at a time. 

Start with the places you dream about. Talk to people who have been there. Use the planning tools available to you. Stay flexible. And don’t be afraid to adjust your plans along the way. Some of our favorite memories came from changes we never expected to make. 

Most importantly, remember that your itinerary doesn’t have to be perfect. Ours certainly wasn’t. We learned as we went, made adjustments, and came home with experiences we’ll never forget. 

If our story helps make planning your own adventure feel a little less overwhelming, then this blog has already accomplished exactly what we hoped it would.