Planning Trips is a Pain in the Ass!

What are your travel planning hacks?

Sep 20, 2013 · 8 min read

The truth about trip planning

Got your attention? If you connected at all with the title then you, like me find planning a trip daunting, a lot of work, time consuming, tedious and really sometimes an overall pain in the ass.

What really happens…

So you finally booked vacation time off and you’re excited as hell. You may have a specific place in mind or not but you’re already in day dreaming mode whether it be the sweet serenade of waves crashing into the beach, discovering new ruins, chowing down on some amazing food or getting lost in a maze of city streets. Pretty sweet right?

If you’re not the one responsible for planning then you’re sitting pretty easy but if you are the one that’s gotta make this dream a reality then it all sets in and you realize…”crap I don’t know anything about these places.” Booking is one thing and that’s a big task on it’s own but lets just focus on the other step which is figuring out. You’re a complete stranger to where you want to go so what do you do?

  • Which cities/countries you want to go to
  • How many days are you going to spend in each city/country
  • What order you want to do these places
  • Where do you want to go see
  • What places do you want to eat
  • What kind of transportation your’e looking at
  • What’s the budget you’re working with
  • etc.

The list of things to think about gets pretty overwhelming. So how do I get this figured out? You’re usually in a position where you’ve volunteered to plan this, you’ve been delegated to do it or you realize that if nobody plans it, this isn’t going to happen.

Initial instincts for building an itinerary

I’ll lay out exactly what I used to do to build my itinerary. This is assuming I have a general idea of where I want to go and I know how many days I have to work with more or less. So subtracting the Kayak/Hipmunk and other flight searching

  1. Figure out what I should be doing in each city
  • TripAdvisor – probably my go-to source still. You have to deal with fake reviews and the phenomenon of being self fulfilling/self selection bias (top ranked will always get propelled to the top) and it’s hard to discover off the beaten track stuff, it’s still good to find out at a quick glance what are the must-sees.
  • Lonely Planet Book – Yep I used to buy the books and read bits and pieces of it but to be honest I never found them that useful. There are high level mentions from the authors but it’s hard to see how well something is ranked as opposed to another. I still bought it in hopes of using it as an emergency resource when on the road.
  • Google – “Just Google it” was usually the mantra. I’d use your typical terms like “top things to do”, “must see”, “[city] guide” etc.
  • Blogs – This is ironic. I would land on a lot of blogs but funnily enough I always found blogs too much work to read unless they really summarized it and made it in a list. Some sort of quick summary helped.Other useful sites that would come up – Frommers, Fodors, Lonely Planet site, tourism boards/destination marketing organization sites.

2. Food and hotels

  • TripAdvisor – Yep again. Find your top hotels but probably try to filter out the high priced ones and see what’s – Pretty much my go-to source to figure out of it’d be worth it to stay at a hostel in a city (cost-wise)
  • Expedia/Travelocity/Venere/whatever the regional OTA was – I guess this phase is kind of like your flight searching but just came later in the planning stage.

3. Organizing it all

  • Word – I’d use Word as a note taking tool when things were still pretty random. When you’re roaming around the web there’s just so much information happening. Crazy overload. So you try your best to manage it. Copy and paste is your friend. I’d copy in links, quotes, photos etc. — Okay it’s still a mess at this point.
  • Excel – The next upgrade. At this point I’m ready for more organization so I’d use Excel to basically help me break down what each of my days are going to look like. Probably easier to show you some screenshots of what I created.
Word scribbles
Spreadsheet madness

Trip planning mini evolution

The mini eureka

  • Wait a second…I’m not sure if I trust a lot of these sites. Are they recent? Are they real people? Are there some off the beaten stuff that would be really awesome to do? Are there others doing the same research and asking similar questions?

A forum world

  • It’s at this point when I start really delving deep into forums. The two that were always provided the most wealth of information were:
  1. TripAdvisor forum – nestled in TripAdvisor and hidden to those that don’t know about them but super useful. A bit more family oriented/business travellers but there are a lot of independent travellers like you and I on there as well.
  2. Lonely Planet Thorntree forum – a lot of backpackers are on here but we’re talking aout a lot of passionate users that are willing to help. Search your question and you’ll find something.

The power of the sample itinerary

  • I think this is when my life was made a lot easier. Before, I was literally cobbling together my itinerary by starting from scratch. I’d scour the web. Get dizzy doing it and then slowly try to put something together that would make sense and would be feasible.I then thought…wouldn’t it be easier if I just found some other guys that have done something similar to what I want to do?This strategy is super easy. Why not look for forum threads or google results that involve “itinerary” or “x day itinerary in y”.Just like that, I was able to find either kick ass blogs or forum threads that had people either asking the same things with awesome people responding with high quality answers OR people just sharing their own trip reviews/trip reports.Something like this for me literally cut my planning time in half. I’m not saying you should copy someone’s itinerary verbatim but use them to mix and match what works for you.What I loved about this was that I was getting real life itineraries from people that had just gone to where I was going to go. It was fresh, non-markety and informative. With so many ways an itinerary can be put together, I could use these sample itineraries as a way to get a flavour of each, look at the similarities, read feedback on the places they went, what worked and didn’t work and go from there.

Google is taking over the world

  • With the advent of Google Docs, this totally changed things. Instead of isolated Excel or Word files, I was able to use Google Spreadsheets to pretty much do the exact same thing I was doing before but be able to in parallel collaborate with friends to help out. Now it’s so much easier to delegate roles where some people would be responsible for the planning of one country while others do another country.

What about what’s out there right now?

To be honest I haven’t been really satisfied by some of the new sites that have cropped up these past few years. Without naming names, here’s the beef I have.

Stop trying to re-invent TripAdvisor

We already have a crowdsourced platform where people can rate and review places they’ve been. Too many sites are focusing on the same idea of reviewing individual places but maybe with some additional layer of more social media integration. It’s just not really all that useful. I still have to go through the work of spending more time vetting out these places on another platform like TripAdvisor that are recommended since it’s hard to trust the reviews of a smaller platform with fewer people on it as opposed to the bigger guys. I still have to go through the trouble of putting together a plan. Ultimately, knowing some top places to check out is fine and dandy but that doesn’t mean I can just take that and make an itinerary out of that. You have to factor in logistics, travel, distance, time required at each place etc.

Curated/auto generated itineraries

I’ve seen so many of these right now. ”Where do you want to go” + “pick your dates” + “pick your theme of travel” = your itinerary. I don’t know about you but having some fixed options on how I should be doing my travel does nothing for me. Does your system REALLY understand what I want? Do I really want to trust some AI built into some back end that spews out an itinerary? There’s no real context to how the itinerary was put together in the first place and no feedback from someone that’s done it. What it forces me to do is again vet out the places they picked for me, figure out what I like and then basically build it from scratch again. Not useful!

The next evolution

Even with the discovery of leveraging sample itineraries, the problem still was that everything was extremely scattered. You really had to be a super online searching sleuth to find these treasures. If you didn’t have the patience, you’d give up pretty fast and you’d never get a good enough sample size to make a good informed decision.

What I’m really envisioning and have for a long time is really ONE place where you could search for sample itineraries. One mega database that would have the largest collection of itineraries for trips all around the world. You’d be able to type in something like “7 days in Thailand” and you’ll be able to sift through 10-20 different itineraries. From there, build an itinerary based on the ideas of others and bam you’re ready to go. Super easy, super fast, super simple.

What do you think? I’d love to hear your thoughts! What are your itinerary building hacks?


    Written by


    Blogger @goingawesomeplaces. Addicted to travel. Travel photographer. Point hoarder. Adventure freak. Love talking itineraries and trip planning.

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