Trip Planning is a Pain in the Ass!

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.  

The truth about trip planning is that it sucks but does it have to be?

What really happens when trip planning

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 let’s just focus on the other step which is figuring out.  

Here are probably a few things that you’ll be thinking about:

• 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

The list of things to think about gets pretty overwhelming.  So how do I get this figured out?

This is totally you.

If nobody plans it, no one else will.

-Every trip planner

Even folks on Reddit agree, trip planning does suck.

How you might be building your itinerary today

Let me lay out what I used to do to build my trip itineraries.

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.  I’ll leave out tools like Skyscanner for now.

1. Figure out the “things to do”
   • 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 Guides – 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 websites.
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 left.
   • Hostelworld – 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/Booking/Venere/whatever the regional OTA is –  I guess this phase is kind of like your flight searching but just came later in the planning stage.
3. Organizing it all
   • Word – Whether it’s Word or some sort of notepad tool, I just needed a space to dump all of this information I was collecting from roaming the web. It’s a crazy overload of copy and paste.
   • Excel – The next step was usually to bring things over to Excel to help break down what each of the days were going to look like.

The below is an example of a trip to Kauai and the random notes I put together from copying and pasting various blurbs that I found.

From all of those notes, you then slowly piece together everything in a spreadsheet in a calendar view.

How trip planning has evolved

As technology has developed and I’ve developed my own keen sense of what works for me, this is a little insight into how my trip planning technique has evolved over the years.

Skepticism of the web

The internet is a great and powerful source of information but when you start diving into your trip planning research, you quickly start identifying which ones are good and which ones are flat out bad.

It really comes down to:

• How recent are these posts and has the information been updated?
• Are these written by real people for the purpose of actually informing (I’m looking at you TheCrazyTourist, TripSavvy, and to some extent TheCultureTrip).
• Are the places written about just the standard spots or are there interesting off-the-beaten-path places too?
• Have these people actually been there?

The web is still the wild west. Knowing what a good blog or website looks like is key.

The power of forums

I’m a huge believer of user forums. In the “old days”, many of us would rely on two different spots: TripAdvisor Forum and the Lonely Planet Thorntree Forum.

Both fo these spots are a wealth of information albeit difficult to search. This is where real travellers could ask real questions and be answered by real experts.

There’s a real commitment to putting the right thing in the search bar for the forum and sifting through pages of threads to find something useful but when you do, it’s usually something miraculous like how we found our private guide in Cambodia or our trekking guide in Chiang Mai.

The power of a sample itinerary

It’s no secret that I’m totally an itinerary guy. Here’s why.

From my rudimentary days of trip planning, I realized that the process was made 10x easier if I could see what other people have been able to do in a certain destination for the same number of days that I’d be there for.

This is when I started building into my trip planning process the trick of searching on forum threads and Google for “itinerary and “x days itinerary in y”.

The result is usually either someone doing a trip report on the TripAdvisor Forum as an example or a blogger writing in incredible detail what their itinerary looked like (shameless plug for my itineraries) and how it went down.

So how do you use sample itineraries?

Individual places to visit are great and all but the magic of the itinerary is in how it’s all strung together.

By seeing a few examples of how others have done it give you really good idea of how to approach your trip from a logistic and feasibility perspective.

You can simply just copy someone else’s itinerary verbatim and then mix and match it with your interests and schedule to make it your own.

This cuts your trip planning time in half.

The Google Suite

No this isn’t about using Google as a search engine but taking advantage of their office tools.

Google Docs and Google Sheets has made my Microsoft Word and Excel obsolete on my Mac.

Why?

• You can instantly share and collaborate with friends and family
• Free to use
• Universally available to everyone that has a Gmail account.

What about what’s out there right now?

As some of you may know from reading my bio, you’ll know that I was in the travel startup space.

Find My Itin was what I attempted to build and I did exactly what I’m telling other entrepreneurs not to do. Building a tool or app to help with trip planning just doesn’t work.

Over the years, I’ve continued to monitor the scene. Many have come and gone and all have come to pretty much the same conclusion.

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.  

It’s 2022. What am I using for trip planning?

Well first of all, there isn’t much travel going on these days but in looking at 3 of my last BIG trips, there are a few new ideas and old ones that have stuck.

Trip planning examples:

• 2 weeks in French Polynesia
• 10 day Egypt itinerary
• 14 day Greece Islands itinerary

What I use to plan trips today:

• Google Sheets – If you read my piece on The Art of Trip Planning, I still use that spreadsheet template for every single trip. What I’ve found is that while I love getting into the weeds of trip planning with my side notes, a spreadsheet is what makes it easy to understand, not only for me, but for my travel companions. I love that I can make the itineraries offline on the Sheets app for me to refer to as well.
• Custom Maps – Most people don’t know this but Google has something called My Maps which allow you to create custom maps. They’re based off of Google Maps but self-contained. You can create different layers, pin with different colours and icons. I love how this allows me to visualize where things are and their relation to one another. The only drawback is that you can’t access the pins offline even if you use the technique below.
• Offline Maps – For a long time Google Maps and the somewhat secret offline feature was what I used to access my custom maps I’d build especially for food-focused trips like Tokyo. However, not being able to access the data offline was a deal-breaker so I either had to add the pins manually on Google Maps or turn to something like Maps.Me.
• Blogs are still the most valuable – The reason I continue to pour tons of effort into creating thorough itineraries is because I know how useful they are. When someone can really walk me through how their trip turned out on the island of Folegandros let’s say, I can create my own version with confidence.
• Pre-booking tours – This applies more for city trips but I’ve been leveraging more of what’s on Viator and GetYourGuide to slot in experience-based tours into my itinerary.

The next evolution in trip planning

I don’t predict that this will change too much over the next few years.

While I’d love to see some sort of itinerary aggregator where you could easily search “10 days in Thailand” and see all of them in one place, the reality is that this’ll never happen.

Content creators like myself want to keep this valuable content on our own blogs. There are also too many platforms out there trying to do this with limited success (think Lonely Planet’s Trips app).

While I’d love for everyone to use my trip planning template, I know not everyone is a spreadsheet nut.

In the end, the KISS (keep it simple stupid) mantra is more true than ever.

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