How to plan a travel itinerary like a pro

Have you ever felt overwhelmed when trying to fit all your travel dreams into a single trip? Well don’t worry, because this happens to almost everyone while trying to organise a holiday, no matter how many trips they have planned. 

I envy those who can come up with a plan on the fly, not knowing what hotel or guesthouse they will end up sleeping that night or even what country! (Okay maybe I don’t… flying blind like that sounds way too stressful for my liking, but it would be cool …maybe).

However, I strongly believe that having a well-organised itinerary is the key to stress-free travel. By removing the big what-ifs from your plans, you can focus on the day-to-day experiences of your trip, resulting in a much more enjoyable experience.

This guide is your first step to honing your travel organisation skills and making trip planning a breeze.

Keep reading to find out how!

Tip One - Define your Priorities

When we were planning our long-term journey across the globe, we started with the intention to do as much as we could and see as many places as possible. Our expectations were high (I’m pretty sure we had every continent on our initial list, bar Antarctica) and we kept extending it month by month to squeeze extra places in. But reality (and our budget) soon set in - we needed to sit down and decide what we really wanted to do.  

This mindset is important whether you’re planning a big long-term trip over several months, or a quick weekender away. Setting realistic expectations is key to avoiding the disappointment of rushing around or not getting everything done.  

Trust us when we say we have been on trips that were so full of things to do that we felt like we needed a holiday from our holiday! Whilst this can be fun for some trips, if your main priority of the trip is to have a break and unwind from a busy work schedule, it might not be the best approach.

My first tip would be to write a list of everywhere you want to go on your trip. Then, list everything you could possibly do on your trip that interests you even slightly.

Once you have an insanely long list, go through each item, comparing costs, travel time, and similarities between activities and locations. Rule out anything that’s a definite no and make note of the non-negotiables. 

You will end up with a nice list of varying activities and locations that you actually want to see and do. Even still, this list might be a bit too long. That’s where the next couple of steps come into play.

Tip Two - Research, Research, Research!

I know research is not everyone’s favourite thing to do, but trust me, a little research into a place before you decide to go there can save you a lot of time and stress once you arrive.

When I say do your research, I don’t mean you have to know everything about a city before you arrive. But figuring out the local currency, transport options, and local customs can be quite important.

For example, (maybe anecdote about Cambodia and using USD - got USD out before arriving in Cambodia which was handy as the taxi driver charged in USD? Or something else?).

It’s also useful to know if any public holidays are happening when you visit. The Taj Mahal, for instance, is closed on Fridays. Imagine planning to visit Agra for just one day, only to find the main attraction shut!

Another crucial aspect of research is finding out the high and low seasons for your destination. During the low season, certain activities and restaurants might be closed. But you could score great deals on accommodation just before peak season. You need to ask yourself: Can I handle the rainy season in Southeast Asia in exchange for lower prices and quieter attractions? Or would I miss out on the buzz of peak season? 

The Taj Mahal, a bucket list experience (closed on Fridays!)

Tip Three - Map it out (literally)

The easiest way to see if your trip is viable (time wise) is to just plug each of your destinations into Google Maps and visualise the route. This can help you avoid unnecessary backtracking and identify the best places to stay. It’s also a good way to spot any attractions or activities you might have missed earlier.

You will thank yourself later when you’re not enduring a 6-hour bus trip for the third day in a row to get to your next location or activity.

In terms of activities, try clustering them by location to save time and energy, especially in larger cities. While we don’t usually plan our activities down to the minute, we like having a general idea of what we can do together and what requires a full day.

Our planned route around Tasmania, Australia in early 2024

Tip Four - Set Realistic Timeframes

This tip really brings together everything—prioritising, researching, and mapping.

Once you’ve pinned down your destinations and activities, make sure you look at the allocated length of time of your trip to determine whether it’s all realistic. No one enjoys a week of 8-hour days of sightseeing without a break, so plan some downtime too!

This was one of the hardest things that we had to do while planning for our 9-month trip; that is, accepting that we can’t do everything.

What we like to do is create a table to mimic a calendar and start slotting in activities. Then, we add travel times using Google Maps or public transport timetables. If your table is overflowing, it’s a sign you’ve packed too much in.

It’s not to say that it’s not possible, but if you’re going to be stressing about how long you can stay at one place before you have to catch a train to the next, it’s going to impact on your overall experience.

This is especially true for longer trips. You might have the stamina to pack a lot of things in a 2-day period, but by day/week/month 3-4 you’ll start to get tired and stop enjoying your time.

You also need to factor in any additional circumstances such as jetlag, layovers and even the weather. For example, visiting somewhere that is very hot in the middle of the day might mean you want to schedule some down time by the pool or in the aircon, saving your activities for the early morning/evening.

Keep in mind that some destinations may be prone to transport delays (another reason to do some research!), meaning that it might take longer than expected to get from A to B.  

A screenshot of our plan for our trip to Tasmania, Australia in early 2024. We just made a table in google docs!

Tip Five - Be Flexible

You might be wondering; how can you stay flexible with a well-organised itinerary?

Being flexible doesn’t mean “winging it.” It means allowing room for the unpredictable.

I can tell you right now that no matter how well you prioritise, research, map and plan, there are always going to be things popping up that you can never predict. 

For example, build in extra travel time as a buffer for delays. If everything goes smoothly, great! You’ll have some extra time to relax or explore. But if things don’t go to plan, you’ll be grateful for that buffer.

Another instance is arriving in a city during an unexpected festival. You might find some attractions are closed—but it could also be an opportunity to experience something unique.

Instead of getting annoyed or upset that you didn’t catch this earlier, embrace it! One of the coolest things we found out while in Bangkok was that a rare event called the Royal Barge Procession was happening the weekend we were there. Yes, it meant that the ferries were cancelled, some roads were blocked (contributing to even more chaotic Bangkok traffic) and some attractions were closed; but it also meant that the city was at its best with fresh flowers and decorative flags put up around the city, not to mention we got to witness a really cool event that we will likely never witness again!

Most importantly, be flexible with yourself. If you’ve had a rough night and the day’s plan feels too much, adjust it. Don’t push yourself to do something just because it’s written down.

Sections of Wat Arun in Bangkok were sectioned off or had restricted access due to the Royal Barge Procession - but the gardens and city were decorated beautifully in return!

Wrapping It All Up

By following these tips, you'll have a solid foundation to plan a more relaxed and enjoyable trip. And remember, staying flexible doesn’t mean giving up control—it means planning well enough to embrace the unexpected.