6 Travel Planning Questions to Start Planning a Trip

Getting started on planning for travel can be tricky.  There is so much to do in you begin to plan for a trip. It may appear quite overwhelming and you may ask yourself, “where should I start?”

Why not use the five W’s and one H?  They are used by journalists, researchers and police as a means of understanding the complete story on a subject.  If you apply them to planning your vacation it will mean that you should have a full understanding of what type of holiday you are trying to plan.

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How to Start Planning Your Trip with the 5 W’s and 1 H


“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 need?  Use this FREE travel budgeting plan.

There is much to discuss when planning a holiday with family and friends – you need to have that communication open.  Allow for 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 planning a ski holiday to a region when you only have the summer available to travel.

pink flowers next diary planning when to travel
When are you going to travel?
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Which leads us 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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If you need some inspiration on where to travel check out this article on Where to Find Holiday and Travel Inspiration.

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 accommodation offer only a twin share price – meaning you will have to pay double for the room.

Booking sites like Wotif* 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.

man opening door to hotel room
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*.

So with all these questions answered are you booking a flight, cruise, or planning a road trip?

Tell me about your travel plans in the comments.

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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 🙂
  • So, your answers need to be descriptive, not necessarily at great length but with some thought by all those involved in the travel planning process.
  • Once you have answered these question you are now ready for the next step: Research and to start budgeting for your holiday vacation.
  • The next step is to learn How to Research Your Trip – START NOW.
  • If you still need to save for your dream vacation follow this budget plan for travel to reach your travel savings goal sooner.

This article on how to start planning a trip was the first in our travel planning series. Continue to read the entire

Travel Planning Series



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Hi, I'm a Perth born and raised travel tips blogger/writer with over 20 years of experience in airlines, hospitality and tourism. Whilst in my younger years I backpacked throughout Europe, these days I enjoy luxury family holidays to South East Asia or road-tripping about Western Australia with my partner and our son.
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6 Responses to “6 Travel Planning Questions to Start Planning a Trip

  • 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!

    • 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.

  • 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

    • 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.

  • 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.

    • 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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