Trip Planning Tools and Tips for a Stress-free Vacation

I love travelling. One of the things I like best about taking a trip out of town – aside from the trip itself – is pre-trip planning.

To date, I have visited 118 cities (and large towns) in 12 different countries. When I was younger, I traveled mostly with my parents or school groups. Since other people usually took care of most of the planning, my involvement was minimal at best.

I started getting more hands-on with trip planning when I booked a trip to Shanghai and Singapore in 2011. My early attempts at trip planning consisted of simple, plain text bulleted checklists I saved in Google Docs.

I broke my lists down into 3 main categories – To Do, To Buy, and To Bring.

The lists served as useful reminders of things I wanted to do at a particular place (including events, meetings with friends, etc), things I wanted to buy on my trip (country or city-specific items and souvenirs), and travel items I needed to pack.

Over the years, I grew to enjoy the trip planning process more and more. Being the documentation geek that I am, I wanted to create travel documents that would be:

  • visually appealing – before, during and after the trip
  • easily reusable – as a template for future trips’ planning
  • sharable – to allow for collaborative planning efforts with my travel mate(s).


To keep things simple, I did everything in the cloud (online). Since I already use Google Drive for my everyday life, I simply created a new folder named ‘TRAVEL’, and sub-folders for each different trip. Google Drive also makes it extremely easy to share individual documents, sheets, maps or whole folders with travel mates.

My trip folders are usually named with the year and the city or country short form, eg. ‘2017 JP / VN’ for my recent trip to various cities in Japan and Vietnam.

Here are the main types of items I put in the trip folder:

  • Flight e-tickets (PDFs)
  • Hotel / accomodation reservation confirmation documents (emails, PDFs)
  • Travel insurance documents (PDFs)
  • Itinerary spreadsheet (Google Sheets)
  • Custom Google map for each Country (made with Google My Maps)
  • Miscellaneous pre-booked e-tickets for events, concerts, museums, tours (PDFs / Word Docs)

Having all the important documents in one folder and available online makes it quick and easy to pull up any info you may need on the go. (I am a huge fan of the Google Drive / Sheets / Docs mobile apps.)

3 Useful Trip Planning Tools

Moving on to the main part of my trip planning – the 3 key tools I use are Trello boards, Google Sheets and Google My Maps.

Trello Boards

Trello boards are ideal for the earlier stages of trip planning – when ideas are being brainstormed, possibilities are being explored, and you just want to keep track of all your ideas in a coherent and organized way.

For my last trip, I created a Trello board as soon as I had made the decision to go. This was months before the actual trip. Doing so gave me and my travel mate lots of time to leisurely toss ideas onto the board as we came across or thought of things, slowly figure out many of the more complicated trip logistics, and organize the planning for our large trip into smaller, more manageable chunks. Here’s a link to a sample Vacation Planning Board template I made to share. You can simply copy the board and fill it out with the specifics of your own trip.

Google Sheets

The next tool I use for my trip planning is Google Sheets. I’m slightly biased, because I personally love spreadsheets. I prefer spreadsheets over simple Word documents, for anything, almost anytime.

I usually have a ‘To-Do’ checklist table in the first tab, a table itinerary in the second tab, transportation and accommodation info in the third tab, a general ‘Notes’ tab, and a ‘To Bring’ tab. This set-up is highly reusable, so after creating this Itinerary Spreadsheet for the first time, I was able to reuse my own template over and over again for future trips.

Here’s a link to my Travel Itinerary Template. Feel free to copy and build off of it.

Google My Maps

Last but not least, I always create a custom Google My Maps map for the place(s) I am visiting. I can’t emphasize how useful having a custom travel map is. It helps you to gauge distances between places you want to visit, as well as make better decisions when selecting your accommodations. Seeing all the points you have added on a map also helps give you an overview of your trip, and how you can approach planning your daily itinerary. When you are finally on your trip, having this custom map handy on your mobile device also really helps.

So there you go – these are my trip planning tools and tips for a stress-free vacation. I’ve been using these tools and making revisions on the formatting over the last few years. The best part about all this is that you can simply make minor edits to the documents during and after your trip – and viola – after your trip you wind up with a compelling collection of digital memories. This is perfect for crafting up post-trip posts (blogs, photo albums, etc), especially if your memory gets a little fuzzy with regards to what exactly you did during your fun-filled trip.

Please feel free to drop me a comment down below if you:

  • found any of this information useful,
  • downloaded, used, or have any feedback on any of my templates, or
  • have any great trip planning tools and tips you would like to share.

Happy trip planning!

3 thoughts on “Trip Planning Tools and Tips for a Stress-free Vacation

    • I usually access it from my Google Drive after first creating it there (Google Drive > NEW > More > Google My Maps).

      On mobile, all your My Maps are easily accessible via the hamburger menu in the Google Maps app, under ‘Your Places’ > MAPS.

      Hope this helps! 🙂

      • oh cool! Yea, i always end up going to and not being able to find it. this trello board layout is pretty cool, I use trello pretty heavily at work for organization but never thought of it for travel

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