The joy of planning

I'm not sure which I love more; travel or the process of planning to travel...

I admit it; I am a planner. This wouldn’t be surprising if you’ve read my previous travel blog posts. 

Planning was a critical part of my prior career, and I have been good at, or at least enjoyed, planning since I was a kid. My professional planning required arriving at a target at a precise moment. But it also taught me that a perfect plan is just the framework you improvise from. As the popular synopsis of Motke the Elder’s saying goes, “No plan survives contact with the enemy,” or my favorite modern take from Mike Tyson, “Everyone has a plan until they get punched in the mouth.” 

Knowing that the act of planning is more impactful than the actual plan is essential. I find comfort in the plan’s structure and enjoy the freedom to play around in real time. Never be too rigid with your plan. 

Travel brings an entirely different element to planning because I know that whatever work or frustration I go through will be rewarded by a rich experience later. I am writing about this because I’ve been planning a trip my wife and I will take this winter. We’ve always wanted to experience German Christmas markets together. This year, we are taking some time to do so while also experiencing the Christmas holiday in a city and country we’ve never visited before, Prague, Czech Republic. 

The trip itself is not cosmic, but I have tried to use every travel hack I’ve learned to make this trip as comfortable and luxurious as possible while spending as little money as possible. Most of the time, luxury and frugal spending are not friends, and we are certainly not flying first class or staying in penthouse suites. Still, it should be a nice trip with some good travel hacks and judicious use of credit card and reward account points. 

I have followed YouTube travelers Kara and Nate for several years and picked up a few mileage/points and travel hacking tips from their journeys and the companies they created, Fare Drop and the Daily Drop. The key to maximizing points for travel is lots of research and a little luck in timing. 

Thanks to a Fare Drop price alert, I got round-trip flights from New York to Prague for my wife and me for less than the going price for a round-trip ticket for one person. Honestly, I think our flights could be categorized as a “mistake fare” because they were ridiculously cheaper than the regular pricing.

Once the airline tickets were secured, it was just a matter of figuring out which cities to visit and in what order and using our credit card points and travel portals to book hotels. I’m happy to say that we now have our rooms booked for the stay, and we paid almost no money out of pocket for any of them. To top it off, we still have enough points left over to cover the train tickets we will purchase to travel between different cities on our trip. 

All these savings mean something crucial for the trip: more money for fantastic local foods and shopping at the Christmas markets. I will write more about the journey as it gets closer. Still, I felt the need to celebrate my love of planning and the fact that I have now completed the framework of our upcoming excursion. Will every event unfold as I have designed? Probably not (I hope the flights go according to schedule), and that’s okay.  A little unpredictability and spontaneity are part of the process and should be embraced.

Also, for those of you who have followed my blog for a while now (thank you!), you may notice something is a little different. My blog has a new home at Substack, so the email notice you receive may look slightly different, but rest assured, it is still me.