Perfect Planning: How To Create An Itinerary

Sunset over the Black Sea in Sozopol, Bulgaria

One of my biggest Global Debauchery fans is my “little” cousin, who’s actually going to be 21 this summer. She’s done a fair bit of traveling with her family growing up, but recently embarked on her first solo international trip to Amsterdam and Berlin. She had some difficulty forming her itinerary and requested that I drop some itinerary know-how on my blog. So, Baby Cuz, this one’s for you: “Perfect Planning: How To Create An Itinerary.”


Where Do I Even Begin?

The #AdventurePartnerForLife and I have, like, fifty places on our bucket lists, of course. We’ve been fortunate enough to check off a nice number of them, but this actually makes choosing our next destination even harder since all the really compelling destinations are done.

How do we even start? Well, I’m somewhat of an avid wanderluster, so I subscribe to a number of great travel blogs and I even collect travel inspiration coffee table books. One of my favorite books to get every year for Christmas is Lonely Planet’s annual Best In Travel. This let’s me check out up-and-coming locations, which usually equates to affordable locations off the beaten path (my favorite).

Yes, cost is obviously one of the major drivers in how to create an itinerary for us. Until more recently, we were very much budget travelers, and we still won’t pay for something just because we can; it needs to make financial sense. The best way to save money to a specific destination? Travel during the shoulder season. Also, have a couple places in mind and scour some discount travel sites to see if there are any offers to one of your places. All set with your location selection?

Determining Your Sights

Once we’ve picked where we’re going, we order our favorite books and do a deep dive. We particularly like DK Eyewitness Travel Guides, but Lonely Planet has a big selection of e-books if you’re looking to pack light, be green, or just keep your place clutter-free. While we’re waiting for our new arrival, we do some preliminary research online. We tend to Google Image search, helps us see what the hype is really all about. (More on our favorite travel resources here.)

Now, it may seem over the top, but from there, the #AdventurePartnersForLife actually start a Google Doc. This is the real start of how to create an itinerary. We make lists of everything we want to see from our books and online and rank them into must-sees, nice-to-sees, and if-we’re-in-the-areas.

Why do we go through all this trouble? Because we only have so much time and we want to make certain we don’t have any regrets. We’ve done a trip or two where we’ve winged it, but actually, they haven’t been nearly as exciting as the well-planned ones we’ve taken.

After our last fly-by-the-seat-of-our-pants trip, we decided planning was the way to go for us, personally. If we had extended timelines or never ending holidays, we might be a little more casual in our approach. If you’re not as anal retentive about your itineraries as I am or just don’t have this kind of time to invest, I really do recommend DK’s walking tours or Rough Guides’ suggested itineraries.

Creating Travel Routes

From our lists, I organize sights by area and route. There are any number of ways to do this, some easier than others. A lot of times, it just so happens that most of our must-sees and nice-to-sees are on DK’s pre-determined walking tours. You could add your picks to a Google map and note the groupings. You could download any number of travel planning apps, add your sights, and look at that map.

We find that we often see a lot more things than we were even intending to just because they were en route to something we really wanted to see. These general groupings save touring time and help me decide where to book our hotels. I also might book a hotel close to a transportation hub if it’s not in a seedy area or if we’re planning to be on the move.

For more ideas on getting from point A to point B, you might find this recent article helpful. We also rely heavily on the transportation sections of our travel books. These educate us on our options and familiarize us with where everything can be accessed, a major component on how to plan an itinerary.

Power Tourist Adjustments

The #AdventurePartnerForLife and I often refer to ourselves as power tourists. We tend to pack a lot into a short period of time, and sometimes even overdo it. My husband, ever the eternal optimist, always shoots for the moon when it comes to our itineraries. If I don’t rein him in, we end up spending more time on the road than actually enjoying our surroundings and we rush from place to place, a practice that leaves us worn out and wanting to sleep more than sightsee. Admittedly, there have been a few times where I myself encouraged the same thing.

Either way, it doesn’t end up being very fun. This being said, know when to cut things out, and be selective about what you want to spend your time doing. The truth is that there will always be more that you wished you would’ve seen, whether in the destination you’re visiting or one you haven’t been to yet. The idea is to get the most out of the time you have. And to enjoy it. You’re still out in the world experiencing something new. Don’t take that for granted.

I hope you’ve found this article helpful in how to create an itinerary, and that maybe you’ve found some new ideas and resources in helping you do so. Not everyone is as structured in their approach as we might be, but for me, creating an itinerary is almost as fun as actually being on the trip. Almost. Other ideas? Comment away below!

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Cheers, Jordan