Planning an Itinerary: What to do when you have ZERO idea where to start

By Emma

Given the present world-wide circumstances that you may or may not have been hearing about, it’s looking a little grim for us hopeful wanderers. Many of us have been faced with loads of free time on our hands. While I’m a strong advocate for being realistic about the goals you set for yourself during this high-stress time, planning trip itineraries has always been a source of catharsis for me. 

But what about those of us who don’t even know where to start? Whether you plan to go solo or with a group, trip planning can be an incredibly daunting process. Sure, there are all the logistical aspects: flights, tours, accommodation…but what arguably is the most time-consuming is the research and decision-making process. Which cities to spend the most time in, which beaches are the least crowded, how much you want to plan and how much you’re willing to figure out on the fly. Of course, how much or how little you wish to plan all depends on your own individual preferences, but we decided that there are some things that every new traveler may find worth knowing. 


This accounts for flights, accommodation, food, and the like. Do as much or as little as you’re comfortable with. Feel like searching out the best restaurants in the area for each and every meal? If you have the time for it, then hell yeah! Don’t want to book your hostels until after your plane lands? That’s cool too! 

My advice is to make a general list of the things you’ll need to at least think about. This can include: transportation (flights are the most obvious, but also trains and public transportation. Ask yourself: is it cheaper to book some of these ahead? Are you willing to pay extra for more flexibility?), museums/attractions, food, and accommodation (again – this depends on your destination. If you’re traveling to Paris in the winter, then yeah, you won’t have to book far in advance. But somewhere that’s going to be busy – like New Orleans on Mardi Gras – or somewhere more remote like Easter Island may take a little bit more planning). 

Again, a LOT of this depends on both the place you’re visiting and the time of year. For example, when Maddy and I visited Edinburgh, we didn’t account for the Fringe Festival falling along the exact same timeline as our visit. As a result, the prices for our hostel were a liiiiitle bit higher than usual. But booking two months to a month in advance allowed us to gain lodging before it all filled up. Which brings us to… 


Depending on your destination and what you wish to accomplish with your trip, it can be difficult to create plans without an organized timeline. How the logistical aspects of your trip fall together becomes the determining factor for this. However, the beauty of travel is that you can be as flexible or as fixed as you wish to be. And yes, this can include your timeline. 

But there are a few things that are universal, regardless of how you travel. Allowing yourself time to get from point A to point B. Taking jet lag into consideration. Having emergency plans for when things inevitably go very wrong. 

The point is, having an idea of when you’re going to be in each place, and deciding whether or not you’re willing to be flexible with this. This brings us to…


Historically speaking, this has always been a significant challenge of mine. What do you do, when you’re visiting a major historical metropolis and only have one full day of sightseeing? Well, you’re going to have to make some difficult decisions. 

Personally, I like to follow my self-coined two-thing rule: 

Pick two things. Two things located in that city/area that you want to do the absolute MOST. Yes, you’ll have more time then that. But if you create your plan around those two specific things, then it’ll give you a good idea – in the geographic sense – of where you need to be that day. For example, if those two things are on complete opposite sides of town, then you know that all you’ll need to worry about is getting from one side of town to the other. If you have more time before, after, or in-between, try to plan those visits within a short distance from one of your two sites. 

Keep in mind, this is best for one or two days. If you’re going to be in a specific area for a longer period of time, it may be a better idea to pick a different geographic region for each day. Or a different theme for each day (i.e. museums one day, tours for another, etc.). 

Although this is the most challenging part of itinerary planning, it’s also the most fun. Create ideas for how you want to structure your days. Use the glorious resource that is the internet to get inspiration, or advice from other like-minded travelers. Check out some of our other articles for help with this. 

If you have any other questions, need advice, or just want to rant, email us at or hit us up on twitter!!

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