The Art of Itinerary

Art by Frankie Fanelli

One lonely night a few months ago, I was sitting in bed, feeling stagnant and stuck. I had been home, or close to home, for a long time, and there was a part of me that itched to get out into the world. I couldn’t get my mind off the fact that there is so much out there in the world to be experienced, and I was stuck in my room re-watching nature films for the fifth time. But as my mind wandered and dreamed of the places I longed to explore, I started making mental lists of the places I’d travel to. Then I thought, why not write all this down?

What then began was a new favorite pastime, where I created meticulously detailed itineraries of the vacations that I would someday take. I got lost in my research for hours, and learned a great deal about the landscapes, cultures, and history of the places I was virtually exploring. Not only has this given me something to look forward to once I’m able to make this trip happen, but it itches that scratch in my brain that urges me to get out there, wherever that may be. I’ve put together a short guide to creating your own itineraries, be they just for the enjoyment of making them, or for a real upcoming trip, anywhere in the world!

1. Pick Your Destination

Every trip starts with a dream about seeing a certain place or places, somewhere in the world. Finding this place is the first and most important step. This destination can be as small or big as you’d like, whether it be focused on seeing every detail of a city, or hitting dozens of cities along a backpacking or road trip. I love reading lists online of dream destinations, or watching travel vlogs on YouTube for inspiration. I recommend the Busy Tourist travel blog, and full-time traveling couple Kara and Nate’s YouTube channel for some wonderful and lesser known destinations. 

2. Map It Out

As someone who isn’t the biggest geography buff, this step is important for me to familiarize myself with my destination before I can lay out the route for my trip. It’s essential to get a general idea of where the major cities or landmarks are in proximity to each other, so I can figure out what the most efficient path is between them. This will also make the following steps easier, so you already are familiar with city names. Even if you aren’t certain of which specific places you want to visit yet, get familiar with it all. 

3. Copycat

By simply searching the Internet for “(Your Destination) Itinerary”, hundreds of options will come up from people across the world who are experts on the area they are reporting on. Find 3-5 of these lists and look through them all to see which specific destinations they have in common, and what each of them recommends (and doesn’t recommend). By compiling your own list based off of the advice of multiple sources, you’ll be sure to have your own unique itinerary that is well-informed and well-rounded. 

4. Listen to Locals

An important tip I’ve discovered throughout my research process is to search out whichever websites or videos that are created by people who call the destination their home. It’s no secret that people are more likely to trust something labeled “Local’s Guide”, but there really is a difference between the destinations your trip will take you to based on the research you do. Local’s guides will take you to those places off the beaten path that won’t be crowded with tourists, and give you a more authentic experience of your destination. 

5. Start Your List

When I first started this process, I thought that I needed to first compile a general list of all the places I wanted to see before starting the physical itinerary, but then I found that as I was making that list, the itinerary was already forming itself. Based on the starting destinations found in the itineraries you’ve researched, plan out your days and which city or cities you’ll be spending them in. In most of my itineraries, I am seeing a country or multiple countries over the course of the trip, so I tend to have a one-city per day rule, and a few travel days throughout the trip to accommodate for longer distances in between. 

6. Plan Each Day

I have found that the best and most realistic way to plan each day is to not plan out an hour-by-hour itinerary, but to simply put a list of sights or experiences under each day, with the exception of booked tours or reservations, of course. Depending on how detailed you prefer your itinerary to be, you can find specific places to go, such as a world-famous restaurant for lunch, or simply write that you’ll enjoy some local cuisine at whichever place you stumble across. In my traveling experience, I have found that some of the best memories and experiences you have during a trip come from the spontaneous changes of plan, and I’ve found that too strict of an itinerary is restricting when it comes to creating these spur-of-the-moment memories. 

7. Accommodations

Depending on how realistic your itinerary is, you can plan your accommodations to be as luxurious or practical as you wish. When planning out your dream trip, it’s so much fun to write down that you’ll stay at a Ritz-Carlton or luxury beach resort, and drool over all of the photos online. But, I also love to find local and affordable places to stay, like AirBnB’s and hostels. Searching online for the best or most affordable places to stay while traveling is helpful to finding your price range and experience. 

8. Getting Around

Lastly, figuring out your transportation to the destination and between them is essential. Finding cheap flights around the world is becoming increasingly easier with websites like FareDrop, and figuring out how much your flight is going to cost you is an important starting point for the overall budget of your trip. If money is no object for your dream itinerary, and you plan on flying between destinations in your private jet, then no worries! One of my favorite ways to plan on getting around in between destinations is taking the train, as it allows for relaxation and beautiful sightseeing. I have planned a trip around a train route and its different stops, and not only did that provide for me a roadmap of destinations, but a relaxing and easy way to get between them.