How To Choose The Best Trip For You: The Ultimate Step By Step Guide

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And welcome to guide 1 of our travel planning series, our ultimate guide on how to choose the best trip for you. If you are new here, check out our Travel planning series summary showing you all the guides in this series.

The first step in how to choose the right trip for you is planning a trip. But there can be a lot to think about. With hundreds of destinations, restaurants, and experiences to choose from. But it is about so much more than that. You should choose your perfect trip based on what you love and what you want to get from your trip is a great place to start. With that in mind, this guide and its planning tools have been created to help you make the best choices for yourself. All with a little serendipity. 

What we have covered

A few points in this post are specific to the UK but they can be used to guide you wherever you call home. All the links we have included are from sources that we use and highly recommend. They are reliable, up to date, and in our view awesome.

So here we go, let us help you to choose the best possible trip for you!

Starting your plan

All you need to choose your perfect trip is a pen and paper, or your phone if you prefer, and write your plan as you go through this post. We have created a free travel plan that you can download to help you. This will come in handy when you get to your budgeting and booking steps making the whole process much easier. If you have children and they want to get involved, we have a tool for them to use too, see here.

Fill in your plan in whichever order is best for you. You may already know exactly what you would like to do and where you would like to go. But here we are going to start by asking, why are you going?

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Look out for our logo throughout this post. This will guide you through the travel plan tool. 

Why are you going?

Think about why you are going when choosing your trip.

When planning a trip, we often start with where we want to go, or what we want to see or do. Which is great, but this could be limiting. Ask yourself, why are you going on this trip? Is it that you want to experience a different culture or to have some quality family time? Maybe you want to relax, to be in nature, or you want some fun and adventure? Or is it all the above? Starting with the why can help inspire your travels with a little serendipity.

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Write a list of your whys in the reasons to go section of your travel plan

Who are you going with?

Think about the people you are going with when choosing your trip.

Your partner, children, parents, or friends? If you are the main planner it could be nice, if possible, to get everyone involved in the choosing process, children included. Asking everyone what their hopes are for the trip you might get some useful, and amusing ideas. You could put their why’s onto your travel plan too. Making sure everyone is happy with the decisions at this stage makes for a more enjoyable experience. 

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Write your guest list in the guests section of your travel plan

Your experiences

Think about what experiences you want to have when choosing your trip.

Using your why(s) it is now time to think about what you want to see and do. For example, if you want culture you may get that by sightseeing or on a heritage tour. To relax you might go to a spa or the beach. For adventure maybe you could go on a hiking tour or swim with whale sharks. And for fun maybe a trip to an amusement park or casino. Write down everything you can do that would get you your why. Think about all the experiences such as the attractions, sights, and things you would like to see or do. 

Thinking about what you want to experience before choosing your destination can be useful. Because, if you are want to see or do something specific, there could be many places you could do this in. For example, if swimming with whale sharks is on your list you could visit the Maldives or Belize, to name a few. 

To help you see how to choose the best trip for you 14 top types explained

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Write what you want to see and do in the experience section of your travel plan

When to go?

Using a planner can really help you when choosing your trip.

When thinking about how to choose the best trip for you, thinking about when to go may influence your choice of destination. For example, if you wanted to go trekking, and could only go away in April, you could climb Machu Picchu in Peru. But climbing Mount Kilimanjaro might be tricky with April being one of the wettest months in Tanzania. Duration, weather, time of year, seasons, and events are all things to consider before choosing when to go.


How long would you like to be away for? If you have a limited amount of time, flying short haul could be better. A quick check in Google flights should give you an estimate of how long a flight will be.


The weather will play a big part in the planning of how to choose the best trip for you, particularly if your “why” is for the sun. Although it cannot be controlled, the weather can affect things greatly. A little research will go a long way as you can try to get the best conditions for your trip. Using websites like the Met Office can be a great resource. It can help you find the best times of year to visit a destination. And you can see weather and climate averages.

Time of year

Usually, the weather is linked to the peak or off-peak seasons. During peak seasons, the price is generally higher. It is often during school and national holidays and will be a lot busier than other times of the year. These times will differ by destination. If you can be flexible and can book during the off-peak season, you could save money and visit when it is quieter. This can also make booking things like restaurants, activities, transport, and accommodation easier.


At certain times of the year, some countries experience more severe weather than usual, like tornados, hurricanes, or monsoons. Again the Met Office can help. Search your chosen destination(s) and you can see the times of year to avoid. As a beach holiday in the rainy season might not be the type of experience you were hoping for.


In some destinations, there might be events that you want to see. This could be the cherry blossoms in Japan or the Singapore Grand Prix. Or it could be a weather phenomenon like the northern lights in Iceland. These all take place at certain times of the year. Check for any events over your chosen dates to make sure you get the most from your trip.

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Thinking about the points above write all available dates you would like to go and the duration in the dates and duration section of your travel plan


The big one is how to choose the best trip for you is your destination. It is time to start searching where you can go based on what you want to do and when you want to go. You may already know exactly where you want to go. But if your still unsure we have created a destination comparison printable to help. Either way researching destinations at this stage will help you get the most from your trip. Sites like Wikitravel and Trip Advisor are great to guide you when researching destinations.

Using our tool

If using the destination comparison tool, make a list of your possible choices. By using the points in this post, you can narrow them down to what is important to you. You might find one has more to offer, such as food, attractions, weather, or culture. You may even get better value for money. Compare each destination using the same dates and duration. 

Estimate the cost

Firstly, make a note of the estimated costs. You can do a quick “average cost” search in google. But for a more reliable estimate based on your dates you could do the following for each destination:

  • Flights: a quick check on Google flights will give you an average price to each destination. While doing this see if it shows the flight duration and make a note of this too. 
  • Accommodation: for a rough idea of costs use Trip Advisor to see what types are available and for how much. 
  • Daily costs: sites such as Lonely Planet offer a breakdown of daily costs based on your budget. This could be stated in the local currency so a quick conversion on XE currency converter may be needed.

Events, time of year and weather

Following the guide above, “when are you wanting to go”, make a note of all events, whether it is during peak or off-peak times, the season’s, and the weather for each destination. Using Wikitravel and the Lonely Planets “in detail” section for your destination will provide you with this information. 


Trip Advisor is a great website to help you see the types of experiences available, the attractions, entertainment options, and more. It will give you a good idea of everything that is on offer. Make a list of any that experience that interest you.

Pro’s and con’s

Now you have your list, you may be able to work out any pros or cons for each destination. Make a note of these.

Your standout “why’s”

Going back to your “travel choices” tool and look at your “whys”, your reasons to go on this trip. Note down any that stand out. What are the highlights of each destination that makes it special to you?

And the winner is…

Hopefully, by now you have a clear destination winner. If not we like to use YouTube to watch some touring videos of our chosen destinations. This helps us to make our final choice. Failing that flip a coin, pull it out of a hat, or ask another member of your travel party for their input.

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Add your destination(s) in the destination(s) section of your travel plan.

How will you get there?

A bullet train locomotive that could be used for transport when choosing your trip.

If you do not have a lot of time, then flying might be your best option. If you have more time and your destination allows it, maybe you could travel by train or bus. Look into the different types of transport you could use. Your choice may be affected by the destination, time of year, price, or availability. These are all things to consider when making your choice. By now you may have done enough research to know the best ways of getting to and around your destination.

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Add your transport details to the transportation section of your travel plan


During your destination research you may have come across an accommodation that you liked the look of. Or you may have found a restaurant or cuisine that you would like to try. Make a note of these now so that you can come back to them when in the booking stages of your trip.

For more information check out our ultimate guides on accommodation and food and drink. We also have an accommodation comparison tool that may help you if you have a few options to choose from, see here. And we have a tool for food and drink too, musts list which also may help you. 

Passes and tickets

For experiences, attractions, and entertainment, there are different options. If you are planning on visiting several, an attraction pass or combination ticket may offer you the best value. These can also be known as city passes. You can also buy these separately. For options and prices see sites such as AttractionTix or Trip Advisor. You can also go directly to the provider too, they may offer the best deals.

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Add anything you found to the experiences and accommodation & food and drink section of your travel plan

Serendipitous tip

You may get stuck choosing between your destinations or type of travel such as a city break or a beach stay. Why not think about doing both? We call this a two birds’ journey. It can be that you visit multiple places or even countries in one trip. This is a great way of seeing and experiencing more. There will be a bit more planning involved in a two birds’ journey, but the extra time and effort will be worth it.  

Next steps

Hopefully, you are full of ideas and options for your upcoming trip. The next steps are included in the following guide for this series: the ultimate guide to the travel essentials

For all our guides in the series see our Travel planning series summary.

Thank you for reading

We hope you found it valuable. Our site and its content are for you our readers, and as such your comments are welcomed and appreciated. If you have any suggestions for future topics and content, please do share them with us. 

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1 thought on “How To Choose The Best Trip For You: The Ultimate Step By Step Guide”

  1. Hello to every one, the contents present at this web page are actually remarkable for people experience, well, keep up the nice work fellows. Deva Renaldo Orlosky

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