Planning

1. Look at train routes before booking accommodations

One of our biggest planning mistakes was focusing on the map rather than the actual travel time between destinations. Two cities may look close together, but once you factor in train schedules, transfers, and travel time to and from stations, a “short trip” can quickly become a 6-hour travel day. 

When planning your itinerary, look at how you’ll actually get from one destination to the next before booking accommodations. Doing this helped us adjust our route and would have allowed us to spend more meaningful time exploring instead of constantly feeling rushed. 

2. Give yourself an extra day in almost every city

If we could change one thing about our itinerary, it would be adding one more day to nearly every destination. Travel days are more exhausting than they seem. Between packing, checking out, walking to the station, taking trains, finding your hotel, and settling in, an entire day can disappear. Having an extra day gives you time to relax, do laundry, sleep in, or simply enjoy a city without feeling like you’re racing from one attraction to the next. 

3. Don’t overpack your itinerary

It’s tempting to try to see everything, especially if it’s your first time in Europe. But some of our favorite memories weren’t famous landmarks. They were sitting at a park, wandering quiet streets, or watching the sunset with a glass (or bottle) of wine. Leave room for spontaneity. You don’t have to check every attraction off your list to have an incredible trip. 

Packing

4. Bring backpacks instead of suitcases

If you’re traveling between multiple cities, backpacks are a game changer. Europe is filled with cobblestone streets, staircases, uneven sidewalks, and train stations without elevators. We watched countless people struggle dragging heavy suitcases across the streets while we simply threw our backpacks on and kept walking. We never regretted bringing backpacks instead. 

5. Pack less than you think you’ll need

Even though we packed fairly light, we still found ourselves wearing the same outfits over and over. Laundry is available almost everywhere, and if you realize you forgot something, chances are you can buy it along the way. Plus, buying a sweater or shirt during your travels makes for a much more meaningful souvenir than bringing clothes you never end up wearing. 

6. Shipping items home is easier than you think

As our trip went on, our backpacks slowly became heavier with souvenirs and a few extra clothing purchases. Rather than stress about fitting everything on our flight home, we shipped a box home through DHL. The process was much easier and more affordable than we expected. If you’re traveling for an extended period, it’s a great option to keep in mind. 

7. Carry a foldable tote bag for groceries or beach days

This ended up being surprisingly useful throughout our trip. Whether we were grabbing groceries, heading to the beach, or carrying snacks for a long train ride. Having a lightweight reusable tote bag made life much easier. It takes up almost no room in your backpack but comes in handy far more often than you’d expect. 

8. Leave room in your backpack for souvenirs.

Don’t pack your backpack completely full before you leave. You’ll almost certainly find things you want to bring home, whether it’s wine, clothing, postcards, or gifts for family and friends. Leaving a little extra space saves you from trying to cram everything in at the end of your trip. 

Accommodations

9. A kitchen can save you a lot of money

One thing we really appreciated was having access to a kitchen whenever possible. While trying local restaurants was one of our favorite parts of traveling, cooking breakfast or dinner a few times each week helped stretch our budget without taking away from the experience. 

10. Think about your evenings too

When booking accommodations, it’s easy to focus only on where you’ll sleep. But after walking 20,000+ steps every day, having a balcony, patio, or a comfortable common area to relax became something we really valued. If you’re traveling with friends or family, those evenings together become some of your favorite memories. 

11. Location is everything

We’d much rather stay in a smaller room in the heat of the city than a larger room far away. Being within walking distance of attractions, restaurants, and public transportation saved us both time and money throughout our trip. 

Budget

12. Track your expenses

We tracked nearly every purchase throughout our trip, from coffee and groceries to excursions and city taxes. Not only did this help us stay within budget, but it also showed us where our money was actually going. By the end of our 3 months, we averaged about $103 per person per day, which included far more than we expected. 

13. Grocery stores are your best friend

Some of our favorite meals came from local grocery stores. Not only are they a great way to save money, but they’re also a fun way to experience everyday life in another country. We loved wandering through the aisles and trying snacks, pastries, cheeses, and drinks we couldn’t find back home. 

14. Budget for city taxes

One expense we didn’t initially think about was tourist or city taxes. Many hotels collect a small tax at check in that isn’t always included in your booking price. It’s usually only a few euros, but over several weeks or months, those charges can add up. 

15. Always carry a small amount of cash 

While credit cards were accepted almost everywhere, there were still times when cash came in handy. Some public restrooms, small cafes, market vendors, or local shops preferred cash. Having a small amount of local currency saves us from unnecessary stress. 

Transportation

16. Learn your rail system before you leave

If you’re planning to travel by train, spend a little time learning how the system works before your trip. Whether you’re using Eurail or individual tickets, understanding train schedules, reservations, and platforms ahead of time will make your travel days much less stressful. 

17. Don’t underestimate travel days

A 5-hour train ride rarely means only 5 hours. Packing, checking out, getting to the station, boarding, transferring trains, and checking into your next accommodation can easily take an entire day. Plan accordingly. 

18. Some trains require seat reservations even with Eurail

This surprised us at first. Although the Eurail Pass covers your train fare, many high speed and international routes still require paid seat reservations. Research your route ahead of time so you aren’t caught off guard. 

Food

19. Make restaurant reservations

Some of our favorite restaurants filled up days or even weeks in advance. If there’s a place you really want to experience, don’t wait until the last minute to book.

20. Try the regional specialty 

Even if it’s something you’ve never had before. Whether it was escargot in France, fondue in Switzerland, or paella in Spain, trying local specialities became some of our favorite memories. You may end up discovering a new favorite dish. 

General Advice

21. Should season (spring and fall) is one of the best times to visit Europe

We traveled during the shoulder season into the busy season and realized how much we enjoyed our days in the shoulder season more. The weather was generally pleasant, attractions were less crowded, and accommodations were often more affordable than during the peak summer months. 

22. Be flexible

Not everything will go according to plan and that’s okay. SOme of our favorite experiences happened because we changed our itinerary, followed a recommendation from a local, or simply decided to explore without a plan. 

23. Slow down

You don’t need to be sightseeing from sunrise to sunset every day. Some of our favorite moments were enjoying coffee in a quiet square, watching people pass by, or sitting along a river with a bottle of wine. Those slower moments are often the ones you’ll remember the most. 

24. Talk to people

Some of the best recommendations we received came from bartenders, hotel hosts, restaurant staff, tour guides, and fellow travelers. Don’t be afraid to ask questions. Locals often know the hidden gems that never appear in travel guides. 

25. Don’t wait for the “perfect” time

There will always be a reason to put your dream trip off until next year. Life gets busy. Responsibilities grow. Plans change. If traveling is something you’ve always dreamed about, don’t spend your life waiting for the “perfect” moment, because it may never come. We’re incredibly grateful we took the leap when we did, and the memories we made will stay with us forever.

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 out
• 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 research everything we’d need to live abroad for three months. 

Some of the things we prepared included:

• Travel health insurance
• Passport copied 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.