Plan a Multi Destination Trip Like a Pro

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 One of my favourite parts of travelling is the planning process, especially when it’s somewhere I haven’t been before. I get such a high! Planning a week-long vacation is fairly straight-forward, but planning a longer, multi destination trip can seem more complicated, but it just takes a little more planning to keep you organized and

Step 1 – Start 2-6 Months Before

Early planning means you have more time to make any changes, to do some research, to compare prices, and learn about where you may potentially be travelling to if you don’t have your mind set on a specific destination yet. Not only that, you take away any stress you might feel trying to book several flights, hotels and possibly train rides within a matter of days. Depending on your budget, how solid your plans are, and where you are going, you can start as early as 6 month! There is, however, such thing as TOO early, especially when it comes to booking flights, which I talk about in a bit.


Step 2 – Know Your Time Frame

This is not only about how much time you have off, but taking into consideration travel time and possible layovers. I recommend a planner or calendar where you can visualize the days. Or better yet, a travel journal! Sometimes you have more or less time than you think. This way you don’t unrealistically plan to do 10 things in one day, when you actually can only do 5, or being disappointed when you thought you would have a full day in Frankfurt but because of the train ride, you only have half a day.
Always be mentally prepared for any delays, such as a cancelled or delayed flight, a late train, a missed connection, etc. Part of being a frequent traveller is to gain the flexibility to deal with all the circumstances that can arise.

Step 3 -Look at and Compare Potential Flights

Depending on where you live and the general places you want to visit, planning early means an earlier booking, which means cheaper flights. Gauge about 3-5 months before your intended take-off as a good time to start booking. If you live in Europe, for example, and want to visit another European country, chances are you can find a cheap Ryanair flight a mere few days before you intend to leave. For example, I’m in Egypt and looking to visit Europe for Christmas, which is a busy season, so to avoid higher prices, I’m booking early October!

Tip: Use good search sites to find lower priced flights, such as Kayak, Ryanair, eDreams, SkyScanner, or Hipmunk. SkyScanner can actually show you when is the cheapest time to book a flight to a certain destination.

Step 4 – Make Final Decision and Book Flights

This could easily be the first step for many travellers, but maybe you’re the kind who starts with an idea and then figures it out as you do more research and figure out options, or are struggling with choosing because you want to go everywhere! There have been a handful of times where I am sure I will be going to, say, Budapest and Prague, but then as I do research and realize that it will be summer and I want to take advantage of beach weather, that I change my mind and decide to go to Barcelona instead.

This step can have some revisions as you go between step 2 and 3, or as you begin to check out flight prices. Maybe you realize flying to Brussels is cheaper than to Amsterdam and decide to take a train from one to the other. At some point, before you officially book, you should have a relatively solid itinerary, especially if you are doing multiple cities and countries. But don’t freak out about having every little detail planned, and if you are doing a fair amount of non-flight travelling, you open your schedule up to flexibility.

Step 5 – Book Places to Stay

Destination chosen: Check. Flights booked: Check. Next is lodging. Whether it’s a hotel, Air BNB, Couchsurfing or other means, be sure to secure a place to rest for every night of travel, if this a several months-long kind of trip, try to book at least a couple weeks in advance during high-season (May-October). The last thing you want to worry about is finding a hostel that has room for hours on end or being forced to check in to a pricey hotel that cuts into your travelling spending money. Both of these have happened to me for different reasons, and it is NOT fun! I know some travellers like to live more on the edge and only plan a few days in advance, but it bit me in the butt and I did not handle the situation very well. To each their own! I just prefer to err on the side of caution.

Tip: Read the reviews and keep location in mind. I always look for walkability and distance from public transportation to make sure I can not only get around the city easily, but to and from the airport as well.


Step 6 – Research Your Destination

Once I knew which cities in Germany and Russia we were visiting, I began looking up on Pinterest the top things to see as well as other tips from other travel bloggers, such as how to travel in these places cheaply or what to do for free. Sometimes I do this before choosing my official destination. Yes, I have sometimes made a decision of where to go simply because I found out there was a museum with a famous painting in City X that I really wanted to see!
When I want to go somewhere, it’s usually driven by the sheer desire to just go and experience what there is to see hear, taste and smell. Only sometimes am I motivated by a particular museum or well-known attraction. But I love knowing about them once I’ve made up my mind where to go! Maybe you function the opposite way, and that is totally fine. Either way, doing this step can lead you to discover tips and information that is immeasurably valuable!

Step 7 – Write it Down

Long trips usually means multiple cities, countries and all kinds of modes of transportation. While on the go, you may not always have internet. In fact, I can almost guarantee that you will be without internet for many periods of time. So my advice? Go retro! Here is another example where a travel journal will come in handy. Print out metro maps to know how to get to your hostel, write down addresses and phone numbers of couch surfing hosts, etc! Sure you can have all of these on your phone or tablet and use it off-line, but we all know how reliable technology can be sometimes…

plan a long trip
There is no real science or one right way to go about planning your long holiday, but these are the steps I do for any trip we plan. I hope you find some direction, and go through your planning process with excitement instead of dread! This should be a fun part of your whole travel experience as you build up the anticipation of travelling!
Who is ready to do some travel planning! What kind of traveller are you? What is your planning process like? Feel free to share in the comments below!
Feature and Pin photo by Pexel

Tags : tips

The author Elizabeth

Christ Follower. Wife. Traveller . Chocolate chip cookie lover. Day dreamer.


  1. Thank you!

    Other than journal-type entries, I put Check-Lists and To-Do lists, sometimes if I meet someone cool I get them to write their name. I make collages of tickets to different places like museums, train tickets, cathedrals, etc. I doodle in it. Oh! And I usually write in phrases in other languages, like when I was in France. I added a ton of French phrases and words that were new to me. Now I'm doing the same with Arabic!

    It also has a neat pocket at the back to carry a map, as well as conversion charts for shoe and clothing sizes, as well as a map with time zones! It's one of my best purchases!

    I highly recommend you get one!

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