9 Essential Questions for Planning an Awesome Trip

Knowing how to plan a trip is essential for making the most out of it. If you plan too much it will be a stressful trip, plan too little and you might lose guidance and miss out on many important things. I’m going to plan a trip from Portugal to SEA as an example.


1. Travel Buddies or Solo?


Most of the time people already know this before they even choose their destinations. Many trip ideas come to us when we are talking with our best friends and traveling with them is an amusing idea to many. Remember that depending on what you want to get out of a trip you should choose if you go solo or accompanied. If you want to see beautiful places, party and have tons of fun, traveling with some friends seems like a good idea. In the other hand, if what you wish is freedom, self-discovery or inspiration, going alone would be a better option, in my opinion.

I’m not saying you won’t party if you go alone or that friends will inhibit you to get inspired, I’m just warning you that before inviting all your friends, you should know that who you choose will have a great impact on your trip, so think wisely about it.

“No road is long with good company” – Turkish Proverb


2. Why Am I Travel?


Figuring out why is it that you want to travel will help you plan better. There are many reasons why people travel and you should know what your purpose is on this trip. Do you want to travel to practise a new sport, try new foods, explore a different climate, learn a new language, be in nature or visit a friend? The more you know about what you want to get out of a trip the easier it will be to figure the next steps.


3. Where Do I Really Want To Go?


This is the most fundamental step of any trip. In order to choose the best destination don’t limit yourself to one place, try to keep an open mind and do some a lot of research beforehand. If you want to visit a big city and New York is the first one that comes to mind, that doesn’t mean it is your perfect destination. Search for other similar options and you might discover that a trip to Singapore is what you really wanted. 

There are many destination guides and top destinations lists made by other travel bloggers. Pinterest is also a very nice search engine I rely on it to find the most amazing places.


4. When Should I Travel?


My hometown in the south coast of Portugal is a holiday destination for thousands of tourists each year, but if you come in the winter you will have the worst holiday of your life.

How to plan a trip

Albufeira (My Hometown) 22nd Of October 2016

1- The weather is something you should always check before choosing a destination. If you are going on a long trip weather averages can give you good insights on what to expect. However if you are only traveling for a few days, always check the weather forecast.

2- Knowing when special events occur gives you a good idea of when to go or avoid a certain destination.

3- If you choose to go when the weather is best or when there is an important event going on, chances are it is the turist season. Going a few months before or after the crowds is not a bad option. You might still be able to enjoy the weather and hostels, restaurants, beaches won’t be crowded and prices might be a bit lower.


5. For How Long  Am I Traveling For?


Usually you don’t get to choose this if you are traveling during a small school/work break, but if you can, this is my best piece of advice: It’s better to visit a handful of places than to try and see many destinations on a rush. I usually stay 2-3 days in each place I visit.


6. What Do I Want To Do?


Once you have chosen where and when to go you have to decide what you are going to do there. If you know your purpose you already have an idea of the main things that fall into this category. The first destination of my trip is Seville and my main activities there will be visiting interesting sites. Instead of a list I marked my points of interest on google maps using my smartphone.

How to plan a trip

Don’t forget basic things like accommodation and food. Specially for a vegan like me, it’s nice to do some research on vegan restaurants in the city or supermarkets that would better suit my lifestyle. Couchsurfing for accommodation is an option during this trip, that’s why a few days prior to arrival I will send a few couchsurfing requests, while knowing the location of a few hostels in case no one can host me.


7. Which Route Am I Taking?


Your itenerary can range from a city walking tour to a round the world trip, but you should definitely make one either way.

How to plan a trip

A Possible itinerary For Seville That Covers My Points Of Interest

How to plan a trip

My Route For Andalusia

How to plan a trip

A Possible Itinerary I’ll Follow To SEA (Lines in blue are mere speculation)

Tracing Your Route:


  • Make a list of the favorite places you want to visit and mark them on map.
  • Connect all your points of interest in the most logical way.
  • Don’t plan more than 1 month ahead, because you never know what’s gonna happen.
  • Don’t necessarily follow your itinerary, remember it is only there to guide you, not to constrain you.
  • Feel free to change your route along the way.
  • If you are traveling long-term, make some time to keep updating your route.


8. How Much Am I Going To Spend?


I have written an in-depth guide on how to travel the world on a budget and I highly recommend reading it (if you haven’t before) to save tons of cash or travel more with the same amount money.

As I have mentioned in my guide, traveling costs fall in 3 main categories: Food, transportation and accommodation. Figure out how much you are going to spend on each one of them and you can have an idea of how much you will need to save/bring for that trip. Don’t forget about the costs of a Passport, Visas and traveling gear.


9. Do I Own The Right Gear?


Are you backpacking, bike touring or driving? Climbing mount Everest or going to Hawaii? Do you enjoy camping or you prefer staying indoors? Depending on the circumstances the right gear will be different. If you have followed the previous steps it will be easy to figure out the main theme of your trip and your luggage should go accordingly. 

Depending on where you are from and where you are going you might need Visas, vaccination and photocopies of important documents and some photographs of yourself. Check out my lightweight backpacking packing list and learn how I travel the world with a 17 liter backpack.


How To Plan A Trip (Summary):


  • Figure out who you are going with.
  • Discover why you want to travel.
  • Search for the best destination on other blogs and pinterest.
  • Choose the best time to go, according to the weather and local events.
  • Make a list of your favorite activities.
  • Trace a route (using google maps).
  • Know your expenses.
  • Get the right gear for you.


I hope this helped guys and remember, sharing is caring, so send this article to a friend that would benefit from it, good luck planning your next trip! Feel free to send me an e-mail, PM me on social media or comment if you have any doubts.

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