Ask Kate: How Far Should I Plan Ahead?

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This week’s question is about planning.  Just how far should you plan ahead when you travel?

Hi Kate!

I’ve been thinking of taking some time off my job to backpack across Europe & Asia for several months. I came across your blog while doing some research, and it has been so inspiring! Really confirms that I’m making the right choice. My only question to you, is how in depth did you plan the trip?

My personality is to just go places without a plan, and figure things out as I go along.  However, with a big trip such as this, I feel that it requires maybe more planning (places to work/stay, plane tickets?) But I want it to be somewhat spontaneous as well.. With your experience, do you have any recommendations?

Some people would tell you to just book a flight and take things as they come.  I’m a big believer in flexibility — though not quite THAT much flexibility.  And I also think that planning is a huge part of the fun! Just researching and looking up destinations will make your heart race with excitement!

First of all, plan for your budget.  Europe and Asia have very different costs — a bare-bones budget would cost you $80 a day in Norway or $15 a day in Cambodia.  Have a general idea of how much time you’re going to spend in each region and make sure you have the money to cover it.  Also keep weather and high and low seasons in mind.

Unless you are positive when and where you will finish your travels, I recommend buying a one-way ticket.  My plans in Asia changed all the time, and I ended up losing money when I decided to cancel my round-trip ticket and fly home via England instead of Korea.

As for work, are you planning on short-term work, like picking up a gig in a beach bar, or long-term work, like becoming an au pair in Europe or getting an English teaching contract in Asia?  If it’s the latter, make sure to spend time doing your research.  In countries like Korea and Japan, it’s extremely rare to find teaching contracts that last less than a year.

Also, check your schedule and plan ahead for festivals and other popular travel times.  If you’re planning on being in Valencia for Las Fallas or Munich for Oktoberfest, make your lodging reservations as soon as you can, because everywhere in town WILL sell out.  Outside of festival time, I book my lodging the day before if I know where I want to stay or if I’m arriving at night.

And this goes without saying, but make sure your travel insurance covers you for the entire duration of your trip.  I recommend World Nomads.  Their policies last up to six months, but you can extend your policy anytime.

Beyond that, remain completely flexible.  The example I always like to give is when I made friends in Sihanoukville, met up with them again in Siem Reap, spent New Year’s with them in Bangkok, and then decided to abandon my plans to head south, instead going with them to Vang Vieng and Luang Prabang.  I had some of the best times EVER with Chris, Jon, Mona, and Anthony — they remain dear friends of mine today and now that I live literally down the road from Chris in London, we still get to hang out all the time!  I am SO glad that I allowed myself the flexibility to make that happen!

Good luck and have a wonderful, flexible time!

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23 thoughts on “Ask Kate: How Far Should I Plan Ahead?”

  1. Im glad you answered this question. Im planning a one year trip to South East asia and Australia in 2014 and I wonder how much I should plan ahead but after reading your blog I gathered I shouldn’t really make any! I know the general places I want to go and the route but beyond that I’m not really planning anything! My friend just took off with a one way ticket and £3000 to Asia with no end in sight!

  2. Great post! I agree that researching for a trip is half the fun. It’s not absolutely necessary to commit to any plans, but it’s good to know what your options are. Partly so that you don’t skip a must-see, and partly because it’s much safer to familiarize yourself with the area.

    I used to completely refrain from making any plans whatsoever. For example, last year while backpacking around Europe, I showed up at 1am in Florence with no where to stay. I had purposely refrained from booking a hostel because I thought that, if I were to commit to any plans, I would prevent other “cooler” options from falling into my lap. I studied there during university and felt overly confident about my connections within the city. Looking back, I was so naive and obnoxious. What actually happened was that I ended up walking around Florence with my backpack until 4am looking for a hostel..only to be turned away by every place I went. Eventually I gave up, took out my sleeping bag, and spent the night outside of a church near Piazza Michelangelo. It was a cold and scary night, but made for lots of memories and lessons learned: Always book your first night in a city ahead of time! Oh, and the other added bonus, I got to wake up with a view overlooking the city…but still, I wouldn’t recommend my former absolutely-no-plans method to anyone!

    1. Ugh, that sounds awful, Kara! I arrived in Kuta, Bali, after midnight and had nothing booked because no cheap places were on HostelWorld at the time. AWFUL trying to find my way down the Poppies Gangs that were shut down, finally paid through the nose for one of the most vile places where I have ever stayed…not pleasant!

  3. Also research visas! Whether you have to get them in advance or can get them on the border, how much they cost and how long they last. One of my friends got kicked out of Thailand because she stayed too long as she didn’t even realise there was a time limit!

  4. I would caution anyone considering a one way ticket. Some countries like Néw Zealand require proof that you’ll be leaving in the form of another outbound ticket. I was able to salvage the situation because I had arrived at my departing airport early enough that I could buy a fully refundable fare to Australia from Néw Zealand. The airline said they couldn’t even allow me on the plane without some proof that I was leaving Néw Zealand and claimed that they could be fined etc. It all worked out and it was the best trip I’ve ever had in my life.

    1. Yeah, I was thinking the same thing – when I first travelled to the UK I was firmly told off at the check-in desk for not having a return ticket. I was going for a fall semester abroad, and I wasn’t sure yet whether I wanted to stay over Christmas. Eventually they made me buy a flexible return ticket instead of going over without one.

      I think it’s different across different places – but definitely worth checking before you arrive at the airport!

    2. Very true, AJ and Kerry — BUT you can always create a fake itinerary out of an old Expedia itinerary in your email. I’ve done that dozens of times with zero repercussions.

  5. The more experience you have traveling, the more flexible you can allow yourself to be. But, if you’re just starting out, or haven’t traveled for sometime, I think it’s always important to do a fair amount of research beforehand. Too many things can go wrong if you don’t have the necessary information.

  6. Great post Kate! I would venture to assume that everyone here is interested in hearing what goes into “planning” a long-term trip. I know I really appreciated your answers. I’ll be teaching in Spain next year and in researching English teaching programs all over the world I know there are a ton of them, especially in Asia.

  7. I’ve been having the same debate for this summer. I’m doing a month and a half trip to Europe with a Eurail pass and have more or less planned out my entire trip, but wonder if I should abandon the plans and just wing it a bit more. My previous trip to Europe was during the offseason and being spontaneous was rewarded. For example, I arrived in Interlaken, Switzerland in the evening with no reservation and a sweet old lady came up and offered me a nice apartment for $15 a day and she did my laundry when I left for the day. In the peak tourist season, I’m not confident I’ll be so lucky. I guess most of my reservations are 10% for hostels so cancelling wouldn’t be a huge deal if I want to stay somewhere. I’d usually lose about $8-$10 by cancelling each reservation. A good portion of my trip is in Italy in July and I’m afraid it’s going to be so packed with tourists that fatigue will kick in really quick. We shall see.

  8. Agree that its best to keep it flexible. Its good to do a lot of research to find out about places and events so that when you are in a place, you will know some things you want to see. However, by tying youself down to a set itinerary may force you to miss out on opporunities that you never anticipated.

  9. Chill Educational Travel

    Thanks for the info Kate. I am planning on travelling after I graduate college this May. I have started planning my trip and came across your blog. I will definitely keep in mind that things do change and I will definitely meet amazing people along the way 🙂

  10. I am so OCD when it comes to planning. I love it and could do it all day long (yes I am that sad), but I agree sometimes you just have to go with the flow. I would have never met my husband if I hadn’t changed my travel plans before I met him in the UK all those years ago.

  11. Great post, although i’m total the opposite. I don’t plan at all. Last time I went away i got a one way flight to Singapore and freestyled the rest. I will simply get a list of 10 things I MUST do, the rest of the time i’ll meet new people and go for a ride wherever they go. I like surprises and uncertainty, and thats the best way to get it.

  12. I always book a night or two at a hostel when I arrive in a new place and try to arrange my flights so that I arrive at my destination in the daytime.
    I ended up booking a RTW ticket and it works for me as I can change the date of my flight whenever I want. I know where I want to go on this trip but I’m flexible with the dates in case I meet others who I want to travel with ect.
    I have seen people who plan each day of their travels and turn down invitations from others because they have already booked excursions ect. I would rather just take each day as It comes!

  13. Great advice, Kate. I’m more of a planner and love researching destinations and the price of flight tickets. I’m more of a planner, but have learned to become a bit more flexible and learned more about my own travel style (I NEED rest days).

    For my trip, I’ve planned how long I’m spending in each place when it comes to the USA and Colombia – they’re big countries, and getting from A to B in each one takes a while and requires advanced planning! Yet when it comes to Europe, I’m going to allow myself more flexibility.

    Good call on doing the research about longer-term jobs, too. Korea needs A LOT of research, given that some jobs there can be fairly dodgy, yet some folks still jump at the first job offer without even asking the most basic of questions.

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