How to Plan Great Itineraries: Intro & Table of Contents

Maxim Kraft
The Tour Team
Published in
3 min readJul 19, 2019
A monkey sitting on an orange pillar with a drawn-on Tour-themed travel backpack. Monos Digital. Haha. Get the joke?

Hello everyone!
My name is Maxim. I am one of the co-founders behind Tour, a mobile trip planning app for iOS (and Android soon). We started working on Tour about a year ago out of personal frustration with how hard planning trips was. All the apps and websites that meant to help weren’t really that helpful at all. We then started a project dedicated to making the ultimate trip planning app, called Tour. Eventually, we decided that Tour would need to become much more than just a project, and today we are working hard to continue improving Tour for the hundreds of users making thousands of trip plans.

As you can probably guess, this means my team and I see hundreds of trips and have to do a lot of research on this topic. I routinely participate in travel subreddits and communities, reading people’s trip reports, analyzing itineraries and sharing advice for other travelers. My cofounder and lead developer travels very often, and always uses our product, inevitably creating many trip plans of his own.

Lately, I began noticing that the itineraries people created didn’t always lead to better experiences. As a matter of fact, many travelers were very frustrated with how difficult itineraries were to make, and that after all the hours of meticulous planning, traveling didn’t necessarily become any more enjoyable. However, it is my belief that with the right tools and techniques, trip planning is not only fun and exciting, but can lead to tremendously better travel experiences. While we’ve found success building the right tool—Tour—the best practices for planning itineraries are still challenging to find.

So I decided to write this guide on planning good itineraries. In my own research, I’ve found that bloggers primarily go over things like passports and transportation, not really the more specific elements of trip planning. As such, this guide will primarily go in-depth on the qualities of great itineraries and the do’s and don’ts of trip planning, with helpful resources throughout the series.

In the next 6 articles, I will go over the different aspects of what makes a great itinerary. Don’t worry, I will try my best to keep them under 10 minutes of reading time. Here is a Table of Contents, with clickable links for published materials, for the entire guide:

Introduction & Table of Contents
So, what makes a good itinerary?

1. Quality Over Quantity: A Manageable Number of Destinations to Visit.
2. Making the Most of Your Stay: Fill Your Active Days Right.
3. How to Not Get Bored on Your Trip: Variety.
4. It’s About the Journey: Activities as Pointers, not Destinations.
5. Need a Vacation From Your Vacation? Just Have a Few Rest Days.
6. It All Comes Down to Balance: Active and Rest Days in Equilibrium.
What to do when planning a trip?
1. Avoiding Unhappy Accidents on Vacation: Safety First!
2. Budgeting for Great Trips and Success
3. Avoiding Unhappy Accidents on Vacation 2: Reserve Everything
4. Avoiding Unhappy Accidents on Vacation 3: Transport Edition
What not to do when planning a trip?
1. The Guide to Stress-Free Trips: Don’t Make Strict Plans
2. On Vaccines and Travel Insurance
Conclusion & Resource Cheatsheet


Feel free to let me know if you think I missed something and share your own experiences in the comments.
Don’t forget to follow the Tour team on Medium for more awesome posts!

Best wishes, Maxim Kraft.

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Maxim Kraft
The Tour Team

Co-founder & CEO @ Tour, drag & drop trip planning app. Volunteer CFO @ Helpful, incubator for projects dealing with Covid-19. Love travel, aerospace, economics