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Developing An Itinerary:

How to Plan a Travel Route Like a Pro

Wanna know how lil ole, inexperienced Alex planned her first travel route abroad? I printed a picture of Europe, taped it to a bulletin board, thumb tacked the cities I wanted to visit and connected it with string. Pinterest would love this method, but as an actual means of route planning? Lol, turns out that’s a big N-O.

Before I started traveling, I naively thought proximity was the only factor to worry about when planning a travel route for your vacation itinerary. Oh boy was I wrong.


Check out my top tips on how to plan a travel route below!

Timing Will Determine Your Trip Route

Multiple factors go into planning your route for a trip, but length is one of the big boys – whether you’ll be traveling for a quick week, month, or even a year long adventure. Everything will ultimately revolve around the amount of time you have to spend in each place.


What KIND of Traveler
Are you?

QUICK WEEK GETAWAY SEEKER: Probably works full-time, not much PTO but loves traveling – when you can squeeze it into your busy schedule. You want to make sure you’re getting the most out of your vacation time so you’ll try to fit in as much as possible into your itinerary.

ONE MONTH PLUS CLUB : You may be taking a sabbatical from work, maybe you’re a student on holiday break. You have a little more time to see everything you want. You’ll probably stick to one region and explore a few countries to truly get a sense of the area.

THE LONG HAUL – FEW MONTHS TO A YEAR: You have time on your hands to really dig in. You’ve either saved up for a trip of a lifetime after quitting your job or have merged into digital nomad territory (or both!). You’ll probably explore multiple regions with the flexibility to stay in places that you end up liking longer.

Pick a Place, Any Place: Choosing Your Destination(s)

Now that you know how much time you’ve got, what tickles your fancy? Is it in the middle of winter where you live and all you can imagine is a bikini and drink in hand? Or maybe you’re the adventurous type, your vacations are all about getting your blood pumping doing activities like hiking, bouldering, surfing or cliff diving.


Ask yourself some of these questions to get started:

  • Do you prefer warm OR cold temps?
  • Ocean, mountains, desert OR big city vibes?
  • Close to home OR far, far away?
  • Is language a factor? Does English need to be widely spoken?
  • Do you prefer quiet nights OR a vibrant nightlife scene?
  • What does your ideal accomodation look like? Hotel with all the ammenties? Airbnb with a kitchen to cook in? Or more of a budget savy, social traveler who likes hostels?

Siri, What’s The Weather?

Are you happiest getting a suntan or breathing in crisp, mountain air? Research the average temperatures in the area for that particular time of year. Be prepared so no surprises pour down on you during the trip.

Check Local Calendars For Events & Holidays

Events in an area can make prices skyrocket. Before booking your vacation do some research into the area to ensure no significant events or holidays are occuring that may bring a surge of visitors.

Or alternatively, look up events for cool things to do! I’ve unknowingly booked trips over local holidays or events (like that one time I accidentally went to Liverpool when they won the Champions League last year LOL), but most have ended up being some of the best parts of my travels.

Liverpool the day after the Champions League win 

Oftentimes where I go revolves around music festivals, so I’ll plan my route accordingly. But if you’re headed to a location where there’s a big event taking place like a festival, plan on having to spend more $$$ on things like accommodations and local taxi services.

Greta Van Fleet | Exit Festival, Serbia
↓↓ Jungle | Field Day Festival, England

Money, Money, Money: What’s Your Budget?

The second most important factor for your route is budget. Are you a high baller where money isn’t an issue? You wanna have a good time with your hard earned money. Or maybe you’re more like me, living that backpackers budget life and probably eating Cup of Noodles right now. Maybe you’re a little of both.


Lower Budgets Should Opt To Stay In Places Longer

If you’re working with a smaller budget than staying in one place for longer will help stretch your buck. You’ll get better prices staying in an accommodation for longer and you’ll spend less on transportation costs.

For lower budget trips think about staying closer to home. The less you have to spend on getting there, the more you can actually spend exploring!

Wanna expand your trip budget? Check out my realistic (keyword *realistic*) tips and tricks to save for a year of traveling.


Truth: Higher Budgets Have More Flexibility

If you have a mid to high range budget for your trip it’ll allow the flexibility of taking the quickest transportation to places instead of the most cost efficient. That way you’ll be able to see and do more on your trip.

Cash In Those Credit Card Points

If you’re not already doing so, I suggest getting a travel rewards credit card ASAP. I’ve been utilizing credit card points to purchase flights since college. In the last 3 years, I’ve almost never paid full price for a transcontinental flight.

If possible, credit cards should exist solely as a way to garner free travel rewards. Never spend more than you can or be prepared for those interest rates to eat you up. When I have to spend lots of $$$ on a big purchase (like my MacBook), I’ll open a new credit card line in order to get the signing bonus. Then put every single purchase, from food to toilet paper, on that card. Pay your card off weekly to help keep track of your spending habits.

However, be selective with how many credit cards you open as it will affect your credit score. I only have two credit cards and can personally recommend any of the Capital One or Chase Sapphire line of credit cards.

Getting From A to B


Consult Your Route With My Main Squeeze Rome2Rio

Rome2Rio is still one of my numero uno travel apps/websites that I consult while traveling. Once I have an idea of where I want to go, I’ll pull up Rome2Rio either on my computer or through the phone app.

Rome2Rio is like Google for transportation. Add your starting destination, type where you’d like to go and click enter. It’ll then pull up all the possible routes to get from Point A to Point B via bus, car, train, flight or ferry and approximate cost. When you click on the transportation, Rome2Rio will connect you with the local companies to book it directly.

I’ve found Rome2Rio especially helpful for navigating between small towns. Many times no direct routes will exist between two smaller towns and instead, you’ll have to catch a connecting bus/train/etc. in a bigger city. Rome2Rio will show you exactly what combination of transportation you’ll have to take to get to your final destination.


Research Flight Prices on Skyscanner & Google Flights

Whenever I need to fly, I turn to the OG’s – Skyscanner and Google Flights. They both serve the same function: finding you all the variations of flights between two places based on your search criteria.

They outline all possible flights, including budget airlines, so you can decide if you prefer to save money by having a longer layover or spending a little extra and securing a direct route.

Skyscanner also has a month feature where you can ask it to show prices for the entire month, perfect for  the traveler planning a route with flexible dates.

Book Longer Flights First

If you’re on a longer trip and have some flexibility, only book transcontinental flights well in advance. You could potentially save hundreds by booking your more expensive, longer flights at least 2-3 months before.

Besides flights within the United States where the price of flying always astounds me, you can save booking the shorter flights in the middle of your trip for later. That way if you’re digging a certain area, you’re not bound to a set time frame because your next flight is already booked.

But always keep an eye on flight prices and book at least a two weeks in advance if possible. Although I’ve also found that even last minute bookings, just a week in advance, won’t break the bank.  


For example: Because holiday flying is always way more expensive, I booked my flight home for Christmas from Dublin to Orlando back in October (using credit card points! Total cost: $47!) even though I was in the Middle East and didn’t have the next couple months planned yet.

This type of travel isn’t for everyone. If you’re the personality who needs a set schedule or know exactly where you’re going to sleep, buy the intercontinental flights first, do all your research and come back to purchase your other modes of transportation.

Travel By Land With Trains & Buses

Consider a Eurorail Pass For Train Travel Through Europe

My first time abroad was a solo, 3 month trip through Europe. Without much international travel knowledge (a.k.a. none, except for a sneaky spring break in San Juan), I purchased a global Eurorail Pass. This gave me the flexibility of having any 10 unlimited travel days within a 2 month span. That way I didn’t have to worry about pre-booking most trips.

Although I would have saved more money by booking trains directly, I’d still recommend a Eurorail Pass for anyone looking to travel with ease and plan on just sticking to Central and Western Europe. I found that most routes I wanted to take in Eastern Europe and the Balkans didn’t exist via train.

Finding Other Train & Bus Routes

Search local or international train and bus routes through Rome2Rio or by simply Googling “A City to B City train routes.” You’ll have to do some digging and possibly some Google translating but you’ll almost always be able to find a timetable online in developed areas.

Occasionally though you’ll have to go old school and actually ask someone. Gasp. Usually locals are more than happy to help or at least direct you to who you should ask. On most buses there will be the option to pay the driver on the bus, but keep in mind that this doesn’t ensure you a seat. Always arrive early for buses or trains you don’t have a reservation for.

Tip: In a few countries (like in the Balkans), you’ll be charged anything from a few cents to a couple dollars for luggage that has to be stored under the bus.

Take Account For Travel Time!

One of the biggest rookie moves I’ve made was not accounting for travel time in my itinerary. In parts of the world where high speed trains don’t exist or infrastructure is poor, it could take you the better part of the day to get somewhere. Even what may seem like a short jaunt in Europe could end end up taking half a day by the time you get to the train/bus station and to your accommodations.

Look Into Overnight Trains or Buses

To save time and money, consider overnight transportation options. I’ve only done overnight flights and trains but I know many people who do overnight buses too. They are never glamorous but will you get you to your destination efficiently and save you from spending money on accommodation for the night. Be sure to load up on snacks and have all your electronics charged for the journey!

Break Up Long Legs of Travel With a Stopover

To avoid traveling for a straight 24 hours, consider adding a 1-2 night stopover in a city along the way. This way you’ll be more rested when you get to your final destination and you’ll get to explore another city.

One way to choose a stopover destination is by seeing where the majority of flights have a layover in on your intended route.

For example, maybe I’m trying to find a flight from Orlando, Florida to Athens, Greece but no direct flight exists. Look where the layovers are happening and choose a place you’d want to spend a night or two exploring. Then book the last leg of the trip to Athens from that new layover location.

How to Organize Your Travel Route

Use Google Calendar to Visibly Plan Out Your Route

If you know me IRL, you probably know I’m a Google and spreadsheet phein. Although I rarely actually stick to all the plans I make, I love planning nonetheless and visibly seeing them laid out.

I created a calendar specifically just for travel and adjust it accordingly as plans change. Another helpful feature is that if you use a Gmail account to manage your travels, bookings that are emailed to you will automatically be added to your Google Calendar.

Since I travel solo most of the time, it’s also a useful tool to share with friends and fam back home so they know where I am.

Pin City Highlights In Your Google MapS App

Something new that I’ve started doing is pin highlights, attractions and restaurants into Google Maps before I get to a city. Usually I do this on the bus or during downtime at night. It’s hella convenient to look at my Google Maps seeing places already laid out with built in Google directions.

If I’m short on time I’ll pin them directly in my phone using the green flag symbol for a site I want to visit and the red heart pin for any recommended restaurants. Below is what I used to map out what to see in Nazareth, Israel (Check out my full Nazareth itinerary here!)

Create Your Own Personalized Google Map

For bigger cities that I’ll be in for awhile, I use my computer to develop more in-depth Google Maps, breaking down each hotspot into color coordinated categories. You can also leave little notes for yourself by clicking on the icon, as seen in the photo below.

Want access to all my personalized travel maps?

Follow me on Instagram at @thewaywardwalrus and DM me asking for which of the following city maps you’d like the link to! You can save the maps on your phone to use for later once you’re there.

  • Amsterdam, Netherlands
  • Athens, Greece
  • Belgrade, Serbia
  • Bucharest, Romania 
  • Istanbul, Turkey
  • Liverpool, England
  • Naxos, Greece
  • Sarajevo, Bosnia & Herzegovina 
  • Tallinn, Estonia 
  • Tirana, Albania 

And now off you go on your next adventure, that much more prepared! If you have any other questions, be sure to leave them in the comments below. Bon voyage travelers!

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