If you’re like me, you’re not much of a planner, your organisational skills are lacking: You have a guy who does your taxes, and you’ve never written up a budget, let alone, stuck to one. So, planning an extended trip to Europe — and beyond — proves to be quite a difficult task.

My Plan So Far

Being a first-time trip to Europe, planning an itinerary is becoming quite the puzzle. With limited knowledge on what exactly to see, I can only really give advice on how to plan your trip, and not what you should actually go to see. It’s a good thing that what you want to do on your trip is a very individual thing, I can’t tell you what dreams to follow.

Saying that, I’m sure I will end up on the well-beaten tourist trail for a good part of the trip, just because most of us have similar ideas of what we’d like to see on our first time to Europe (eg. Colosseum, Pisa, Eiffel Tower, Louvre etc.).

Planning vs Seat of Your Pants

Like I said, I’m not an organised person. I was once, but then I decided to start acting on a whim instead of always thinking ahead. For me, at least, it makes things more enjoyable, opens up opportunities and new experiences, and I never know what I’m going to be doing a few weeks in advance. There are downsides to this way of living/traveling, including: not being able to attend Glastonbury Festival 2011, because its already sold out (months in advance); or arriving at a destination for an event, and having all the hostels booked because its July and peak travel season.

So you really need some give-and-take.

Even Rolf Potts agrees that you need to allow for the unexpected in his book Vagabonding: An Uncommon Guide to the Art of Long-Term World Travel. Rolf suggests you travel in a way that allows for adventure to come to you: you don’t need to have every detail planned out months in advance. Especially travelling solo.

On my trip, I’ve decided to book a tour to help me find my feet from the very beginning. I’m also going to be booking several key events and festivals along the way which I think may sell out. And, I will probably organise where I will be for the “high season” tourist months. The rest, I will leave to destiny.

Showing up to a destination without a clue of what to do when you’re then can be disasterous. It’s a good idea to do a little research ahead of time. You don’t have to have every day planned out, but just an idea or two of why you are visiting that place is a good start.

Just take a look at my itinerary page to see how often my 3-day plan changes.

Step 1: What time of year do you want to go?

The first thing you should be doing when travelling a European adventure, is picking the time of year you want to travel. Travelling to Europe in peak season can mean long lines, no vacancies at accomodation, and large crowds. Travelling in the off season can mean closed attractions, or unfavourable weather. If you are planning on taking a long-term travel experience (like I am), it doesn’t matter what season you arrive in, but brings me to my next point… the budget.

Step 2: How long do you want to go for (how long will your budget allow)?

Picking your travel dates is tightly coupled with your budget. If you only have a few thousand dollars, you really need to consider a short trip, or a working holiday visa. How you plan a short trip is going to be quite different to how you plan a long-term trip. I’ve found that many tour companies cater for the short-term trip, with seeing a great deal of Europe in under 30 days. Perhaps you should be looking into this? If you’re moving around quite frequently, it could be worth letting someone else do all the planning for you, and allowing you to just enjoy the ride.

However, if you want to be a little more independent, and feel in control of your own fate, or you have the budget, then start to think about your absolute “must see” destinations in Europe and begin to plan around that. Remember, if you are travelling on the Schengen Visa, you can only stay 90 days in any 180 day period. This can greatly impact your itinerary also.

Step 3: Plot it on a Map

Grab yourself a map, and start to link your destinations together. Obviously, its going to be a lot cheaper to avoid backtracking, and work in a continuous direction. Having an open-jaw type itinerary or the same start/end destination is completely up to you.

Step 4: Ask around, get some advice

Read the guide books, the blogs, and talk to your friends. Find out whats happening where, and on what dates. Just remember, you can’t see it all, and you shouldn’t have to try. Europe has been around for thousands of years, and will be around for many more. So you don’t get to see something this trip, it makes for a good excuse to come back in the near future.

Step 5: What you absolutely “must see” vs. what you can afford to miss

Once you’ve got a brain-dump of all the places you’d like to see, and a vague idea of the direction you’d like to travel. Start narrowing down your destinations to what you absolutely must see, and won’t forgive yourself for missing. Remember to leave plenty of time in your itinerary (if you can), to allow for day trips, and variations from your plan. You never know who you’re going to meet on the road, and thats what makes it such an adventure.

Try to spend 3-4 days in big cities where there are lots of things to see and do. One approach that Rick Steves’ recommends is the home-base approach, where you use a big city destination as your base, and make several smaller trips to nearby locations.

I’m starting to feel like I’ve done too much planning already? How about you? Without even taking into account what days I’d like to be in what cities… I already feel claustrophobic.

If you’d like to map out roughly how many days in each destination, then go right ahead. Don’t forget to take into account the travel time. You will spend a great deal of your time in transit. Luckily, there are many overnight trains and buses you can catch, to fill-in the travel time while you’re sleeping. Make use of these, especially on the long-distance transit legs of your journey.

Don’t pack in too many places in your itinerary that you will always be on the move. Its exhausing to do this. Keep a day here-or-there to unwind and just chillout doing whatever it is you like to do. Jet lag, is also something you should think about; you will know it when you get it.

Step 6: Mark it on a Calendar

Get yourself a calendar, and work out which days you will be in which destination, and which days you will be travelling. This is a great way to see how long you will be travelling, and whether your budget can handle it.

Remember, its ok to change your mind. Its ok not to have a plan. Just be sure to be flexible if things dont go your way because that museum you were keen on visiting is closed, or that hostel you heard about is booked out. If its something you really want to see, book it in advance. Just don’t plan every little detail out in advance, leave some room for that cute blonde you might meet, or that group of backpackers who want to take you on a 8 day trek with them through the East.

Good luck planning!

My own itinerary planning

Now, for where I’m at with my own itinerary. I’ve worked out my start and finishing points. I’ve worked out a few of the things I absolutely must see. I’ve even got my hands on a map. Now I’m just trying to decide between destinations and events that occur at the same time. After I leave Turkey, I’m still not sure whether to head down to Greece and the islands for a bit of fun and sun, or head up towards Slovenia for some adventure… maybe Lake Bled, or along the Danube through Bulgaria, Romania, Hungary, Slovakia to Austria.

So many choices!

I’d say I’ll be travelling clockwise from Turkey to Greece and through Western Europe over a 1.5-2 month period. Attempting to skip the UK until I am satisfied I have seen most of Western Europe. Then heading to the UK or perhaps the East.

I don’t see a problem with having multiple options for an itinerary. That way, if I meet a group who is going with option “B”, I can ditch option “A” and travel with them for a while.

Let me know your planning technique when creating an itinerary for your trip. What has been successful, and what has failed.

** flickr header image credit: Robert S. Donovan

Ian Cartwright

is a guy who gave up his career and mortgage for solo long-term travel. He travelled extensively across Europe for a year before heading onward to North Africa. He is now planning a trip to Latin America. As always there’s sure to be plenty of laughs, tears, and misadventures along the way.