Quick Guide to Planning an Overseas Holiday

Planning my next holiday!

I often get asked to share my advice for planning an overseas holiday, so I have compiled some of my most important points into this quick guide. By no means do I claim to be a travel expert, but for my age, I do have a reasonable amount of experience in this area. In fact, I am currently in the midst of planning my next holiday! This guide is predominantly written with information to suit Australian travellers. However, the basic principles can be applied to travellers from any destination. I thoroughly enjoy planning holidays from scratch (sometimes I question whether I should have been a travel agent) and hopefully this guide will help you to enjoy the experience too!

Initial Planning

Depending on your perspective, the initial planning stages of any holiday can be the most exciting or the most daunting. I always have a very clear vision of when and where I want to go on a holiday, but some people are the exact opposite. That is why all of the most important decisions need to be made in the initial planning. There are a number of questions you firstly need to ask yourself. Here are some examples:

  • When can you actually take the time to go overseas? This is nearly always influenced by external factors such as work or school schedules, so I suggest getting this out of the way first. If you can travel at any time of the year, then congratulations – the world is your oyster!
  • What type of weather do you want on your holiday? Do not dismiss Wikipedia, as it is an easy tool that I use all the time to find out about the climate of specific destinations.
  • How much money do you want to spend? This is definitely my least favourite question to ask myself, but is perhaps the most important. As a very rough guide for Australian travellers, Asia is usually a great destination for a ‘cheap’ holiday, North America and Europe are moderately priced, while South America and Africa typically cost the most money to visit. Definitely remember to keep currency conversion rates in mind.
  • What do you want to do on your holiday? Not every destination has everything on offer, so this will definitely help to narrow down your options in choosing where to go.
  • Are you willing to take further steps to meet entry/exit requirements and ensure your safety while overseas? Some destinations definitely require more attention in meeting entry/exit requirements and maintaining your own safety, in terms of both crime and health. An excellent tool for finding out more about this is the Australian Government’s Smartraveller website. All Australians should definitely check this website before travelling anywhere overseas.

If these questions fail to help you narrow down your options, you can always resort to a website like Adioso. In this search engine, you can literally type in broad searches such as “Brisbane to somewhere warm” and it will provide you with an array of flight options to match. It is great to generate ideas, but I recommend looking elsewhere for more airline options and competitive prices.


Once you have a rough idea of where you want to go, it is time for the really fun stuff! Playing around with flight itineraries is my absolute favourite part of planning any holiday. One thing to remember is that flight pricing is not always logical. For example, yesterday, I found a cheaper price for flights to Las Vegas and Washington DC if I added a stop for a few days in Boston. It is definitely worth playing around with a range of destinations and dates. Kayak is a fantastic website for doing this, as it lets you modify many different search options and it links you directly to the airline to book once you have made a decision. It is my current obsession. Booking directly through the airline avoids incurring any nasty travel agent fees, should you wish to change or cancel your flights at some stage. If you do not mind the risk of such fees and you are a student or under the age of 26, it may be worth checking out STA Travel or Student Flights. They sometimes have cheaper prices for people who meet either of these categories and they have a multi-city search option (which, in my opinion, is essential for any decent flight search engine).


Booking accommodation is much like booking flights – it pays to shop around and be flexible with dates. For example, my searches yesterday showed that it was possible to save hundreds of dollars just by changing Washington DC hotel accommodation to on the weekend (as opposed to during the week) and by changing the reverse for Las Vegas accommodation. My favourite website for conducting hotel price searches is Expedia, as it features a huge range of hotels, has very competitive prices and can show you all of the hotels in one location on a map. Another hotel website worth looking at is HotelsCombined. However, once you have a fair idea of where you want to stay, it might be worth checking whether the price is cheaper directly on the hotel’s direct website. If you are looking for alternative, cheaper options to staying in a hotel, check out Airbnb.

Choosing a hotel can be difficult, as it involves weighing up all of the pros and cons of each hotel. These are the most important qualities I personally look for: a fantastic location (in a safe area and walking distance to major attractions and public transport), an affordable price and cleanliness (I do not need anything fancy, as I never intend to spend much time there). My all-time favourite travel website, TripAdvisor, is the perfect tool for finding your perfect hotel. I do not like using TripAdvisor for pricing (as it lists hotels on cost per night, when I prefer a total cost), but it is invaluable for reading reviews. The amount of hours I spend on this website is excessive.

Sight-seeing and Other Activities

To get an idea of how to best spend your time in any destination, I again cannot look past TripAdvisor. It has excellent forums in which travellers discuss their opinions on what to do in each location. And, of course, there is good ol’ Lonely Planet. In terms of booking sight-seeing tours and similar activities, I recommend Viator. Do not pay much attention to the tour reviews on its website, as they are definitely not balanced, but it is a great way to get an idea of what is available. I have booked several tours through Viator itself and have never had any issue. However, sometimes it is cheaper to book directly through the actual company conducting the tour.

Other Considerations

Do not forget to buy travel insurance, under any circumstances! As the saying goes, “If you can’t afford travel insurance, you can’t afford to travel!”. I have purchased several policies through Worldcare, largely due to the fact that you can design your own policy to suit your needs. However, I fortunately have never needed to claim, so I cannot comment on their service in that regard. Keep in mind that most travel insurance policies do not cover airline insolvency.

And finally, Google can always provide you with an array of further information on any of the topics I have mentioned above – often linking you to blogs like this one!


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