Planning Your Great Adventure

So, my last few weeks have been spent in heavy planning getting ready for some fantastic trips coming up. And it made me realize maybe some people could use some tips on how to plan these great adventures! So for any who don’t know, let me give you a run down on how I plan my trips. It might not be the best method, but it is the one I employ, and it might help others so here we go!

Step 1. Deciding where to go in the first place.

Now this is usually a mix of thinking of places I want to see and checking prices of airline tickets. As I am already in Europe for work it makes things much simpler to get a budget airline to another country. Or train for that matter. Obviously it’s a little different coming from a completely different continent, but nonetheless maybe it will give you some ideas!

I usually begin by using Google flights to hash out what the best options are for the dates I’m looking at. Obviously other travelers might have some good airline website suggestions, but I find the map Google provides quite handy to get some price ideas.

Google flights

Lille is an unfair price representation as they don’t seem to have good flights anywhere…usually I head over to Brussels in order to get bargain flights, but still gives you a layout idea!

If I have a specific destination in mind, Go Euro is also super handy because it will compare airline, train, and bus tickets (and time lengths), so it’s quite convenient if you’re debating which is more worthwhile for your travels! However, I have discovered it doesn’t work for some countries, so just be aware you might have to plan some travels on your own. Rome 2 Rio is similar in this respect although I haven’t used it quite as much. I also recently discovered Inspirock which is fantastic for giving you some ideas of what to do in each place, and what a logical path might be between places. Again, other travelers might have way better suggestions on websites, but here are mine!

So once I have a starting destination in mind I go from there. Yes, I’m a multi city traveler. Traveling with me is no picnic. It is always go go go.

So for example, my latest trip I started with Dublin as my first destination. Now, you as a traveler can always consider the option of flying to another destination further away, but personally I’m a fan of going to your starting destination and taking trains or buses around to closer locations. Examples include doing a central Europe loop (see The Great Train adventure) with Germany, Czech Republic, Slovakia, Hungary, and Austria to name a few destinations. Going up North (see the great Nordic adventure) to try out Denmark, Sweden, and Norway (maybe Finland too if you’re adventurous). Doing a southern trip (see Christmas adventure) down to Spain, Portugal, Morocco etc.

I prefer this method, so looking from Dublin onwards, my map caught my eye with the lovely little Isle of Man between England and Ireland. Well voila next step.

2. Evaluate close options on the map


Trips so far on a map

So once you have your map out you can start looking at realistic and close destinations. Makes it a bit easier. I usually write out a rough itinerary based on what I’m seeing. I don’t even look at planes or trains or anything else, just give myself ideas of where I might like to go.

3. See if your plan works.

So step three comes before even possibly booking. Think of it as a first draft. You need to make sure your plan is feasible. For example, in planning my most recent trip I realized there were limited ferries to the Isle of Man. Didn’t stop me from still deciding to go there, but it did change how many days I was staying in Dublin. From there it’s checking on hostels. When I was booking my train trip I was planning on stopping in Zurich. However, seeing there were few hostels all at very high prices changed my mind. Hadn’t really used AirBnB yet, but you get the idea.


As you can see such high prices for a youth hostel (one of the few options available) made me change my mind about where to go for vacation!

4. Make a more solidified plan

Once you’re seeing if train/bus/ferry/any other transport tickets are working out in your favor, and dates are lining up, and hostels are possible, that’s when you write down a more solid plan to make sure you’re not missing anything. Write down where you’re staying each day of the trip (city/country wise). Look at the amount of time you’ll be moving between places to decide if you’re giving yourself enough time in each city. Revise as needed. And from there you’re going to have a more solid plan of action.


My recent discovery of Inspirock has made it easy to create some layouts that I can later revise if I want. Check out this plan (loosely based on a real trip I did) here. Though note it is merely a representation of cities I visited, not things I did in each.

5. Book transportation

I always book this first. I figure plane tickets especially are good to get booked as soon as possible. They tend to be less flexible in terms of options. Whereas, if you’re staying in a big city there are usually plenty of hostels available, so you needn’t worry about not finding one.

Sometimes I do these two booking steps on separate days, because I tend to feel exhausted after accomplishing one.

Verify you have the right times and dates and everything written down, and you have the bare bones of a trip planned! Again, more revision might need to happen if there aren’t options on certain days, or if prices are just exorbitant flying out at a certain time. It’s all up to you, keep in mind time can be as valuable as money sometimes.

For braver folks, maybe you’ll want to rent a car. I cannot imagine driving in Europe myself, but some might be up for it. Just keep in mind some times and places might have a lot of traffic.


Paris after holidays. Might be a place to avoid driving.

6. Hostel booking…or lodging

So yes,  you might not be hostel folks, but still it applies. Book your place. I’m writing a piece coming up on hostels, so should help any unfamiliar with how to go about that. However, basically it just comes down to doing some searching and narrowing down what works for you. And then from there, booking. I try to write this down in my itinerary too so I can keep track.

Fall break itinerary

The itinerary I made for my first trip. Doesn’t need to be quite this detailed obviously, but very helpful overall!

7. Plan the things you’ll do

Sure, traveling on the fly can be fun too. Some people love that. They might not even book flights or hostels or anything else. Me, I’m a planner. I like to know what I’m doing. My train adventure I didn’t have as much of a plan and ended up regretting it. I’d show up to places and find out it was impossible to get in without a reservation, or find out things were closed that I didn’t realize. Regardless, at least knowing some of what you’d like to do can be good.

However, you can also go overboard like I’m currently doing for the next trip. Booking things to do. Writing down a detailed itinerary of what each day is going to look like. Basically it starts with a trip advisor review of best sights, then a scan of the map to see what is close together and what will take more time or effort to see. And from there, basic itinerary can be drawn up.


Rough draft of what I might like to see in each place I visit!

8. Make some bookings…your choice of course!

Booking things is up to you. Some people find it comforting to know they don’t have to worry about it. Other times you can feel stressed once you get there worrying you might miss an appointment or not have time for something you’ve already paid for. It’s entirely up to you. A little research on what really can be useful to book is good. Also maybe check how busy the dates you’ll be traveling are. It might be high tourist season, in which case having a few advance tickets could be helpful. And sometimes it is comforting to have a thing or two planned. Knowing you’re doing a walking tour in one city, or going on a dinner cruise in another, or going to the theatre in London (guess who has a ticket to Les Mis).

From there it’s just preparing anything else you need and getting excited about the fantastic trip coming up. I still have about a few weeks to go until my next one, but I’m so thrilled by the prospect that I cannot help but continue planning every detail. It’s going to be amazing.

Stay tuned to hear about what happens in England and Ireland coming in April!

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