How to plan a trip

Trip planning can be quite complex, some people enjoy it and others don’t. One thing that I learned is that trip planning is iterative in nature, so do it in small steps and revise multiple times.

Before you start, write down your basic criteria because these affect your planning the most

  • which month will you be traveling: weather can be your friend or foe
  • how long can be you away
  • what is your budget for the trip

Planning the route

Trip Planning

The most important part of my trip planning to establish the trip route. Do check the map and familiarize yourself with the general locations. At this point, what you need is breadth and not depth. Understand the places (cities for example) enough to estimate how much time to spend there. Be realistic because in most of our trips we would never have enough time to spend in one place and this will always be a balancing act.

Check the best way to go from one place to the next place: flight, train or bus. More often than not, you will be dropping in and out places from the route as you research more. You might be overwhelmed by the amount of information but keep the priorities straight: you don’t need to know everything; you only need to know enough to see the big picture – the route.

Once you have the draft route, it is time to check the flights!

Many of us would start from the air tickets; which is a good idea but don’t buy the ticket without having a route. I mentioned about the 3 main constraints above, so if you buy the ticket without a route, you will be working on 4 constraints instead! 

Check different airlines for different combinations of flight destinations, revise your route until you are happy. It is useful to follow the airlines on the social media, so you know the promotions.

Tip: You don’t need to travel in and out of the same city; it may make better sense to fly out from a different city. Yes, the ticket will be more expensive but then again, you would need to spend time and money to come back to the city that you landed. If the price difference is not a lot, I suggest you just pay for it.

*One thing that might affect your route is the price of accommodation. Do check the booking sites a bit, so that you are sure that you won’t be breaking the bank!

Tip: A good rule of thumb is to check for visa requirements if you are visiting a country for the first time. I need a visa for almost every country. The necessary documents for the visa application, processing time and appointment availability: all of these affect my planning.

Trip Planning

Detail Itinerary

Now, we dig into the massive amount of details: understanding the places. These are the areas that you need to check: understand the districts, location of the attractions, getting around and what to eat (this plays a major role in my planning). The best way to understand the city is through the food the locals eat; although this can be a really difficult thing to achieve. I rely a lot on the user reviews from TripAdvisor, it is always a good start.

Plan your day based the opening hours of the attractions, because most of them close on certain days (or free admission for every last Friday of the month, for example).

It is not difficult to get budget-conscious when you start looking into accommodation options but don’t compromise on the location. You might end up spending more money or time for getting around, so it is always good to stay in an accessible place with amenities nearby.   

If you are a solo traveler on a budget, Couchsurfing, hostels and Airbnb rooms are usually the cheapest. For two travelers, I usually find hotels cheaper and more convenient. (Check-in and check-out time especially). If you are traveling as a group, Airbnb usually is a very good friend.

Templates & Lists

If you are not a seasoned traveler, search online for travel templates. You may not find a suitable template but that should give you some ideas how to build one. I do recommend that you build a template based on how you like to structure your information and slowly fill in the gaps.

Another useful thing is to have a list of things to pick. You can write down a list each time you travel but chances are that you might miss out a thing or two; best to have a master list that you can refer on for all trips. 

Going Digital

One thing that plagues me a lot is figuring how much I spent on the trip. I am not good at remembering all the details, so my phone comes in rescue. I use trip expense app on my phone to record all the expenses I made and once the trip is over, I will export the records and update my main travel document with these details.

It is always a challenge to remember the shared expenses with the travel mates (like who has paid for what, who hasn’t paid for what) but we discovered an expense splitting app called Splitwise and it solves the problems. 

Chances are that you might not have an internet connection; so download the offline maps to your phone; you can check your location without a connection.

Supplementary Information

Travel Planning

Pay attention to the culture and customs: know what is considered polite and rude. You might find some customs very strange. Even if you can’t relate to those customs but don’t disrespect them. 

There are scam artists everywhere, knowing your enemy is half the battle; so check out the scams that people have reported. Once in awhile, you might land into a scam. It is frustrating but doesn’t let it ruin your trip. Best if you can talk your way out but if you can’t, the next best thing is to learn from it; share with people, so no one shall be harmed in the same way.

Social Media

I love reading travel stories. There are many travel bloggers who write good posts, so I follow them on social media. Check on their posts on the places that you have been to (even better if it is your hometown or country); that is the easiest way to gauge. Having a good travel knowledge ahead will save your time in planning, good to keep yourself updated with these articles.

You can check on what people posts on Instagram or any social media: with hashtags and locations. These might give you a general idea of what you can expect. Be careful with this though, too much of it will lose the charm when you visit the place, you will just end up confirming what you have seen on Instagram.


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