6 Travel Planning Questions to Start Planning a Trip

Getting started with planning for travel can be tricky.  There is so much to do it can appear quite overwhelming and you are no doubt asking yourself “how do I start to plan my holiday?”

So, let’s begin with the basics to help understand what type of vacation you want.  We’ll do this by getting you to answer six questions to plan your trip.  This will be the first step in organising your holiday.

After you have answered these questions move on to the following articles to continue with your travel planning.  You may even like to sign up for our newsletter to have them dropped into your inbox each week.

Here’s a sneak peek at the entire series (links to these articles at the end of the post):

  • Questions to ask when planning a trip (this post)
  • How to research a trip
  • How to save for travel (with worksheets)
  • How to book a trip
  • International travel documents (with printable)
  • Pre-travel checklist
  • Ultimate travel packing list (with PDF)

But first, let’s get begin with the first step of planning your trip.

In this Article on How to Start Planning for Travel You Will Learn:

  1. Who are you travelling with?
  2. When do you want to travel?
  3. Where do you want to go?
  4. Why are you travelling?
  5. What type of accommodation do you want?
  6. How are you going to get there?
    Discover the entire travel planning series with more tips

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How to Start Planning Your Trip with Six Questions


“Who are you going to travel with?

When you go on vacation it is not just your travel dream it is everybody in your travel party’s travel dream.  So you need to be aware of what they want.  You can’t cater to them or negotiate with them if you don’t know who they are.

You will need to understand their age group needs.  If you are travelling with kids you will need to allow play and rest times.  Or if you are travelling with older people they may not be physically able to participate in adventure activities.

Apart from age needs, you will also need to consider the type of vacation you travel companion wants and what they can afford.

If you plan on going it alone you, you obviously only have your own needs to consider but you will have different obstacles to negotiate.


Not sure how much money you will need? Start by creating a…

There is much to discuss when planning a holiday with family and friends – you need to have that communication open.  Allow each other to express their own travel dreams and find a balance.

group of silhouetted people at sunset
Who are you going to travel with?
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“When do you want to travel?”

Ask yourself when do you have time available to travel?  Then ask your travel companion.  There’s no point going through all the vacation planning if you can’t get time off together.

The other point of knowing when you plan to travel is – understanding the seasons of your destination.  For example, there’s no point in planning a ski holiday to a region when you only have the summer available to travel.

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When are you going to travel?
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Which leads us to the question, “where do you want to go on your trip?”

You need to know which destination you want to visit.  With that, you need to understand the seasons of your destination and the time you have available to travel.

For example, if you really wanted to go skiing in Japan but it’s summer then you may have to change your location.  Or was seeing Japan the real drawcard for the holiday?

part of the world globe
Where are you going to travel?
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Get destination ideas on…

Or check out some of these Lonely Planet travel guides* they are by far my favourite travel guide as they offer not only things to do and see in a destination, but also places to eat and stay.  Plus travel tips on cultural differences, what to expect and how to act without offending your destination hosts.


This now leads you to ask, “why are you travelling?”

Is it to partake in:

  • Various activities: (skiing, hiking, sunbathing)
  • See the sites
  • Visit family or friends
  • Relaxation

Understanding the real reason for planning a holiday will help determine, where you want to visit and the activities you plan to do whilst on vacation.

If you are travelling solo can you join tours or activities with like-minded people and make friends for a day.

lounges under umbrella on the beach
Why are you travelling?
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Now that you know where you are going you will need somewhere to stay on your trip.  So, “what type of accommodation do you want?”

  • Camping/Caravanning
  • Chalets/Holiday homes
  • Hotels
  • Resorts

Again this requires communication with all members of your travel party.  Discuss all the options available and what suits each person and matches the desire of where you want to go and why you want to go on your holiday.

If you are travelling solo then you may have to look for alternatives or the budget to be revised as many (but not all) holiday vacation accommodations offer only a twin share price – meaning you will have to pay double for the room.

Booking sites like Booking.com* can help you view all the latest deals at your holiday destination and you can even narrow the search down to fit your style of accommodation.

Get more details on…

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What type of accommodation do you want?
Image by ming dai from Pixabay


Lastly, and it’s kind of odd that “how are you going to get there?” is last.  Because, when you tell friends and colleagues you are going on holiday vacation you start with, “I’ve booked a flight, cruise or planned a road trip”.  But to choose how you are going to your destination you need to have all of the above questions answered.

  • “Who is going?”  How many in the car or flight/cruise tickets do I need to book?
  • “When are you going?”  You can’t book tickets without dates.
  • “Where are you going?”  Again you can’t book the tickets if you don’t know which destination to tell the travel agent.
  • “Why are you going?”  If you need to carry sports equipment or any other special considerations. You need to find a carrier that can meet your needs.
  • “What accommodation do you want?”  Well, this one you don’t necessarily need to answer now to determine how are you going to get there.  But it is handy to know when the time comes to book your tickets.  Sometimes booking the whole package in one go is easier and cheaper than breaking it up.  Either way, it gives you more alternatives at the time of booking.

Check out prices to get to your destination with Wotif*.

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How are you getting to your holiday vacation?
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Top Trip Tips: How to Plan a Vacation

  • When answering these questions you cannot answer with yes or no.  It is not a question, of “do you want to travel?”  I am assuming that you do as otherwise, you wouldn’t be here 🙂
    • Your answers need to be descriptive, not necessarily at great length but with some thought by all those involved in the travel planning process.
  • Use either pen and paper or a spreadsheet to document all your answers.
    • As you progress through the travel planning stages it can become quite overwhelming keeping it all together with marrying up what everybody wants and what options are available and best suit you.
  • Once you have answered these six questions with beginning to plan a trip you are ready for the next steps:

This article on how to start planning a trip is the first in our travel planning series. Continue with the entire series, if you don’t have time to read them all now sign up for our newsletter to receive each article week by week and also gain access to our Subscriber Library that includes checklists and worksheets to plan your trip.

Travel Planning Series



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  1. Great ideas!! My bucketlist is so long the only trouble I have is narrowing it down. This is a great way to think through the process!

    1. I know the feeling of the huge wish list Amanda. I hope this theory helped you to narrow down your next choice of a holiday destination.

  2. Tons of great tips here, but for me traveling is pretty simple: just me and my hubby and we go where I want to go. End of Story. haha He’s my best travel buddy – everyone else I’ve ever traveled with can’t keep up. #TheWeeklyPostcard

    1. Sounds like you’ve found the perfect travel companion Lolo 🙂 It’s often hard to find a good reliable person that you are still friends with after the trip.

  3. What a great way to think about travel planning and organize your thoughts. For me sometimes choosing where to go is the hardest because I just want to see everything. Thanks for sharing on #TheWeeklyPostcard.

    1. I hear you on so much to see so little time Anisa. To make my decision on where I often use how much time I have to travel when we can go and the budget to help narrow down my choice.

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