I think travel planning is an acquired taste… one that is usually acquired after lots of practice. I used to feel totally overwhelmed when planning trips, but these days, it's one of my favourite forms of stress-relief. Still, there's so much to think about… where to go, when, what to do, and not least of all, how to get there. Over the years I’ve realized that there is an art to travel planning; especially if you, like I often do, want to visit multiple destinations on a single journey.
I’m currently planning a trip to the Nordic countries for summer 2018, so I thought I’d use it as an example as I talk (type?) you through my step-by-step process for planning a multi-country extravaganza. First things first: organization is absolutely necessary when compiling the info you need to make a smart travel plan. I like to keep it old school with paper and pens so I can jot down notes without needing to switch between even more web browser windows than I usually have when planning a trip. So, grab a notebook, and let's get started.
step 1: choose an anchor
If you want to plan a multi-country trip, it helps to have something to build the adventure around. It could be a particular event, or just the time period during which you are free to travel. In my case, my anchor is an 8-day horseback riding expedition through the Icelandic highlands. The ride only runs once per year, on set dates, so I’m organizing the rest of my trip around it. I also know I want to be home on Koh Tao for a festival beginning August 15th, and I try not to be away from my company/ girlfriend/ cats/ home for more than 4-5 weeks at a time, so I'll leave mid-July.
step 2: Figure out where to go
Compile a short of the places you’d like to visit; ideally, they will be relatively near each other, but that’s not essential (more on that later). Especially in Europe, it’s super easy to visit multiple destinations in a short time. Since I’m going all the way from Thailand to Iceland, I ideally want to check out the other Nordic countries (Finland, Sweden, Denmark, and Norway) on the same trip.
This step is also when you’ll want to figure out what you want to do in each place, so you know how much time you need, and whether or not to add/subtract destinations. My fav place to research destinations is Pinterest, since it gives me a great place to store and organize information in a visually appealing way.
step 3: research your transportation options
My life as a wannabe world traveler got 1000X easier the day I discovered Rome2Rio (which I featured on my list of essential travel apps). It’s the single best way to figure out how to get from A to B (to C to D etc).
Now that you’ve got your list of desired destinations, you can start plugging them in to see what your options are for travel, as well as time and costs for each leg of the journey. It’s easy to change the order around until you find the right combo of places in the order that you like. I’m still playing around with different travel routes, but have narrowed it down quite a bit. (By the way if you’ve been to the Nordic countries or Scandinavia feel free to give me your opinion!) I love to travel by boat and/or train, since it allows me to see more of the places I visit, and, especially in Europe, it’s at least as comfortable as flying, if not more so.
Rome2Rio can also show you how easy it can be to get to destinations you hadn’t thought to include on your trip. I realized that it will be really easy to pop over to Canada on the same trip to visit my parents, since there is a cheap, fast, direct flight from Reykjavik to Montreal. It’s a pretty major add-on, but considering how long it takes, and how expensive it can be, to visit Montreal from Thailand, I think it’s going to be worth it.
step 4: Time to (prepare to) fly!
Ok this is when shit gets real. Finding convenient and affordable flights is when things can start getting a bit tricky (or extra fun, depending on how you look at it). I use Skyscanner to start looking for flights. I love the “whole month” search function which shows the cheapest dates to fly your desired routes. If possible, I also consider alternate airports. For example, a one-way flight from Montreal to Thailand is hella expensive, and takes forever, but there are ridiculously cheap flights between JFK and Bangkok. I can either take a scenic 12 hour train ride or a cheap 1 hour flight to get between Montreal and New York, so it’s not unreasonable to add that on, especially if it means I get to see my parents less than a year after my last visit (which has not happened in the 10+ years I’ve been living abroad). After comparing flights on Skyscanner, I realized it'll cost the same to fly from Reykjavik - Montreal - Thailand (via New York) as it would to fly from Reykjavik - Thailand (I have no idea why but I'm pleased), so now I know I can definitely go visit my parents!
Anyway, I digress… but this tangent brought me to another important point: you don’t have to fly round-trip! Especially when planning multi-country destinations, it may be logical to book one-way rather than round-trip flights. In places like Africa and Asia, round-trip flights are just the price of two one-way flights, so it’s easy to fly into one place and out of another. Even if a one-way ticket is more expensive than half a round-trip ticket, it may still be worthwhile to get one-way flights, so you don’t need to spend time and money returning to your starting location.
If Skyscanner gives you an option for an airline with a connection in that airline's core location, hop over to that airline’s website and see if they offer free stopovers. What’s a stopover?… well, a stopover is a long layover. Instead of staying in an airport for a few hours, it’s often possible to extend your stay for up to 5 days at no additional cost! I've had free stopovers with KLM in Amsterdam and Paris, soon I have a stopover in Dubai with Emirates, and FinnAir offers stopovers in Helsinki (plus Turkish Airways in Istanbul, and Qatar Airways in Qatar, to name a few others).
Speaking of which, it’s fine to piece together different tickets. For example, when I just went to Canada and Scotland, my girlfriend and I booked tickets from Koh Samui to Bangkok, different tickets for Bangkok to London, another for London to Glasgow, aaaaand then another ticket between London and Montreal. It was kind of whack but we got great deals this way and it all went very smoothly. Just be sure to give yourself decent layovers as not all airlines will interline checked baggage between flights booked on separate tickets (although Malaysia Airlines interlined with British Airways and Air Canada interlined with Malaysia Airlines without any fuss at all, thanks for looking out guys!). Also, keep in mind that most travel insurance companies will only cover missed flights on separate tickets if there is at least a 3 hour connection time between flights.
step 5: take a deep breath!
Phew, that’s a lot of info to take in, huh? No worries, just take your time, and remember that these steps aren’t 100% linear… it’s likely you’ll need to bounce around between them as your plans progress. Make sure you keep jotting down those notes as you build your itinerary, and before you know it you’ll have your own dream trip all planned out in front of you!
So, in a nutshell, this is my process for planning multi-destination trips. Of course, this isn’t the only way to travel - maybe you prefer to visit just one place and thoroughly explore it. Or, maybe you want to just land somewhere and see what happens. I love adventures like these too - each trip is unique, and that’s the beauty of travel… it gives us the freedom to live out our dreams in whatever way resonates most strongly within us at the time.
Do you have any tips to share, questions to ask, or problems you’d like me to troubleshoot?
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