How to Plan the Perfect Itinerary: A Series

One of the questions we get asked the most is “How did you decide where to go and what to see?” – the answer, as unpopular as it may seem, is lots and lots of work. Whether setting off on a weekend roadtrip, taking a week off to soak up the sun at a beach resort, or undertaking a round-the-world adventure, crafting a solid and well thought out itinerary is one of the most vital and sometimes overlooked steps in the planning process.

Don’t get us wrong, we love a little spontaneous adventure or detour as much as the next backpacker, but gone are the days when travelers can throw caution to the wind and set off without any semblance of a plan – at least without an unlimited budget or unlimited patience. With the increased accessibility to travel for much of the world, booking transportation and accommodation ahead of time and having a plan is becoming more important to make the most of your travel time and budget. This was very evident during our last trip through Europe, where we quickly realized that being organized and well planned out was the only way to ensure we had a bed to sleep in or a seat to sit in when we needed one most.

Crafting a perfect itinerary means striking a perfect balance between rigidity and flexibility – most of us don’t want to get to the point where each and every minute of every day is accounted for (although this may work perfectly for a select few), but we also want to know where we are sleeping before nightfall begins to creep in. While this balance of planning vs staying aloof is different for everyone, with a little trial and error you can figure out what works best for you.

It is for this reason that we’re focusing on travel planning in this series. For us, planning is one of the most enjoyable (and sometimes frustrating) aspects of travel. Sorting out where to go, how to get there, where to stay while we’re there, and what to do is a lot of work – but it also lets us fantasize about the trip before it even begins – sometimes the only way to stay sane between trips. Hopefully everyone will find a suggestion or new idea that will help with their next trip.

If there’s anything you want to know about or you have any questions for us, let us know in the comments or contact us via email or our social networks!

18 Responses to "How to Plan the Perfect Itinerary: A Series"

valerie says:
July 10, 2014 at 12:57 am
Looking forward to this series!
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1. Calli Duncan says:
  July 10, 2014 at 6:25 pm
  Thanks Valerie!
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2. Travis says:
  July 10, 2014 at 10:29 pm
  Thanks Valerie
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Tiffany says:
July 10, 2014 at 2:33 am
Looking forward to finding out how you guys plan things! After a year of floating around pretty much just wherever I wanted to go and barely planning the basics, I could definitely use some good tips. I have a few months of Europe and North America coming up where staying on top of things will prooobably be necessary again
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Michael Huxley says:
July 10, 2014 at 1:08 pm
I do have to disagree slightly here, I don’t think the days of unplanned adventures and throwing caution to the wind are gone, I just think people have become far too overreliant on itineraries and pre booking and websites like tripadvisor.
I agree completely about getting the balance right though and some regions (such as Europe) will always take a little more pre planning than others (such as SEA) but on the whole it is easy to plan the basics and then see where the road takes you from there.
On the whole, the only things I book ahead that are set in stone are my arrival date and my departure flight, and occassionally a pre booked flight(s) during the trip, but that is it. I do pre book my first couple of nights in a hotel/guesthouse when first arriving in a country, or during particularly busy times (religious holidays, FMP etc.) That’s it. The rest of my planning is research, seeing what is there, what I want to see, learning customs/ a few phrases etc.
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1. Travis says:
  July 11, 2014 at 5:28 am
  Totally agree with what you’re saying Michael…it definitely takes the right personality to be so flexible though! I think it really depends on the region you’re going to – in Central American we were just able to arrive in town and find a place for the night and things to do with almost no problems; in Europe on our last trip, however, there were definitely a number of occasions where almost all the rooms in the city were booked up at least a week in advance and transportation prices rose exorbitantly (I’ll give a few examples when I write about this part of the process). Flexibility really does go a long way…I can’t even count the number of deviations from our original “plan” that happened over the last ten months. Thanks for sharing your opinion Michael!
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antonette - we12travel says:
July 11, 2014 at 5:58 pm
I love planning – totally! I agree that you should have a plan, somehow doing things without a plan never really worked, esp since we never travel more than a month and you want to see as much as you can without being stuck or missing out something that you could have added if you tried to plan a bit more careful. I’m looking forward to your tips and tricks in this series…
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1. Calli Duncan says:
  July 12, 2014 at 4:34 pm
  Thanks Antonette – it seems some people are more into planning that others, but I think you are right on when you say that you want to see as much as possible and not miss out on anything and therefore planning is important. Our travel pace is pretty quick too so if something is closed one day it means we might miss it forever and can’t just come back the following week. I guess the degree of planning really depends on our individual travel styles
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Mindi @ 2foodtrippers says:
July 12, 2014 at 6:40 pm
For us, planning the trip is part of the process and the fun of travel. The key is to strike the right balance between plans and spontaneity. I’ll be curious to see your tips.
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1. Calli Duncan says:
  July 13, 2014 at 4:54 pm
  Great point Mindi – planning lets you daydream about the trip before it even begins
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col says:
July 12, 2014 at 8:43 pm
Interesting series ahead. I am a planner and enjoy it but have to say pre-planning is a good idea to an extent, particularly if only visiting somewhere for a short time but..allow time for randomness and spontaneity as you never who you might meet that will lead to visiting sights etc, you didn’t consider.
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1. Calli Duncan says:
  July 13, 2014 at 4:53 pm
  We completely agree Col, there always needs to be some room for spontaneous adventures in all the planning
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Natasha Amar says:
July 15, 2014 at 7:50 pm
I usually plan differently depending on the destination and whether or not I’m going solo. But I do agree that when you have limited time and money, you do need some kind of planning to make it all work. In fact a lot of people do not realize how much effort goes into travel planning.
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1. Calli Duncan says:
  July 16, 2014 at 5:57 pm
  Great point Natasha – travel planning is a lot of work!
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Razia Sheikh says:
July 24, 2014 at 9:10 am
Hello Travis,
Nice Article. I agree with you. We must have a plan while planning to travel new place. Not because of saving budget or anything. Because of you able to see all attractions or best places in that country.
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1. Calli Duncan says:
  August 1, 2014 at 4:46 pm
  Great point Razia, it’s so easy to miss something without some pre-travel planning
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Lina @ Divergent Travelers says:
November 26, 2014 at 3:17 am
There is definitely a delicate balance, especially when you are traveling long term. I had this deluded idea I could just have it all planned out before we left. thankfully I only planned the first 3 months, because ever since then we just go with the flow. I can’t even tell you the changes that we have made to our itinerary and all the new places we have gone to and are going to because we didn’t over plan. It is amazing and such a liberal part of being a long term traveler. We find we plan by the month or so as we go, but that only pertains to destination planning. Many occasions we are booking flights or accommodation the night before!
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1. Travis says:
  November 27, 2014 at 3:45 pm
  I wish we could let go that much I think because it’s been mostly Europe that we’ve traveled through recently that we feel like a little more planning is worth it. It just seems that prices in Europe go up so drastically that planning (at least just a couple stops) ahead is well worth it if you can continue traveling for longer. I think that when we travel to SEA or South America that our opinions will change with the lower range of prices. Thanks for sharing your thoughts, hopefully I can get more posts in this series up and it can start a good discussion. Safe travels!
  Reply

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