Planning your next holiday or travel adventure

So, you’ve decided you want to travel. You’ve bookmarked your favourite travel websites, and you’re ready to get stuck in to that planning your next trip.

As I have already mentioned, planning a holiday is not easy. However, it is fun and it’s so rewarding to do it all yourself.

But, if you’ve never planned a holiday before, it can be super overwhelming—where do you even start?

Which is exactly why I decided to create this Ultimate Travel Guide in the first place: to take away some of the overwhelm, to offer up my tips and tricks, and to encourage more people to create their own holidays and see more of the world.

Pick your destination/s

The first thing you need to think about is the destination.
Pretty obvious, right?

But seriously, writing out a list, creating a vision board, or placing pins on a world map of your dream destinations can make such a difference.

Ask yourself:

Where do you want to go?
If you could spin a globe and point your finger at any location in the entire world, where would you want your finger to land?
What locations excite you?

Perhaps there are multiple places you might like to visit—I whole-heartedly encourage this!

It doesn’t matter how far away, how remote, or how extreme your destinations are: include them all. Sure, you may not be able to visit the entire world in one holiday, but keeping a record of where you want to go in your life is so important—and it’s super exciting to be able to check each destination off once you’ve been there.

Once you’ve figured out what countries you would like to travel to, then you can narrow it down and start to look at the cities or towns that you might like to visit within those countries.

Make a list

Grab out a notebook and pen, or open up a Word document, and create a list of possible destinations.

There are no limits here—it doesn’t matter how big or small your list is, just make sure you’ve written down all of the places that light your fire!

Once satisfied with your list; get out your map, open up Google, crack out the bookmarks I’ve provided, and do a bit of research.

Planning Phase_1

Research the destinations you want to visit

Check out photographs, reviews, or blogs for each area you want to visit; see how expensive they are; what time of year is best to visit; if there are any political, environmental, or safety factors that may prevent you from travelling there.

What places (if any) would you require a Visa for?
Would you need to get vaccinations or shots for any of your destinations?

Make note of all these challenges: while they don’t necessarily rule any destination out, it is important to know right off the bat what hurdles (if any) you may face in planning your trip—and you may need to enlist professional help down the track in some cases.

See how far away your potential destinations are from each other, what modes of transport are available between destinations, and where it might be best to start and end your trip (Rome2rio is a great option here).

Pro Tip:

Map out your ideal travel plan based on your research—I like to create a calendar-of-sorts in Excel to visually display the length of time I would want/need in each town or country, and record how long it takes to travel between each place.

If you already know how long you want your trip to last for, this is the perfect time to start cutting off any destinations that won’t fit into your timeframe—but keep them on your list so you can visit next time! Alternatively, you can start to reduce the days you want to spend in each place in order to fit everything in.

If you’re not restricted by a timeframe, have all the time in the world, or just have no idea how long you want to be on holiday for; then mapping it out will also help you to see just how long your ideal trip will last for.

Taking/getting time off

Planning Phase_2

Which brings me to another key point—asking for time off.

If you work for yourself, have a bunch of annual leave owing, are ready to quit your job for travel, or just have a great boss, then getting time off will hopefully be a breeze!

If this isn’t the case, then you might come across a hurdle or two in requesting leave.

In the past, we have been very lucky to have been able to take 4–10 weeks off work and still have a job to come back to; but we know that not everyone has that luxury.

The best advice I can give you is to:

  • Let your boss know well in advance: the more information you can give them, such as length of time, time of the year, and where you’re going; the better, in our experience.
  • Be flexible with your request: if you are asking for four weeks, but your boss will only let you take three; then you can either work with them to come to a mutual agreement, or reduce the number of destinations you want to visit/spend less time in each place.
  • Reassure your boss that all your important tasks will be taken care of before you jet off, or offer up suggestions for who could potentially fill in for you while you are away. This shows that you’re a dedicated employee, and your boss will generally be more likely to accommodate your request.
  • Plan your trip around public holidays: if your workplace shuts down over the Christmas/New Year period, or another significant time of the year—then this may be your perfect (albeit more expensive) opportunity to plan your holiday.
  • As a last resort, there is nothing wrong with handing in your resignation in order to take an extended holiday; however, it is best to do this if you have a backup plan in place—you don’t want to go on holiday without a job to come back to, trust me!

When should you go?

Planning Phase_3

If you haven’t already thought about what time of the year you would like to take your holiday, then now is the perfect time to ponder that.

As I mentioned, the Christmas period can be a great time to go on holiday—you usually have less issues in regards to taking time off—but the drawback is that travel is way more expensive at this time of year.

School holidays are always a busy travel time no matter where in the world you are, and again prices tend to go up during these periods.

Location, location, location

But regardless of all that, the biggest factor in deciding what time of the year to travel relates to the locations you would like to travel to.

Some destinations are more enjoyable in the warmer seasons, where others thrive in winter. Just as some travellers (read: me) like rugging up in their winter woollies and hitting the snow, while others prefer to chill at the beach with a cocktail (also me).

We’re all different.

The key here is that the experiences you have in a particular location can vary greatly depending on the time of the year you visit.
For example, we first travelled to Europe during Winter. Locals thought we were crazy for including Venice in our travel plans—”it’s a summer destination!” they cried; but we went anyway.
And they were right. It was grey, it was dreary, it wasn’t the beautiful location we were expecting, and we left feeling a bit ‘meh’ about our experience.
Fast-forward a year and half—we visited Europe in Summer, and decided to include Venice in our plans again. It was like a completely different place, and we had a fabulous time.

Planning Phase_4

I’m not saying don’t visit Venice in Winter; I’m just pointing out that some destinations are more suited to certain climates, so it is worth thinking about.

What do you want to do while you’re there?

Another factor is what you hope to do while you’re on vacation.

If you’re a snow bunny, then Winter holidays are totally the way to go! You can go snowboarding or skiing, snow shoeing, dog sledding, ice skating, snowmobiling… the possibilities are endless.

But if relaxing on the beach with a good book and a cocktail are more your scene, then a summer holiday or a trip to a tropical location that is warm year-round is your best bet. You can go snorkelling, swimming, trekking, paddle boarding, jetskiing…. again—the world is your oyster!

It may mean you have to push back your travel plans in order to jet off at the right time of year, but it is totally worth it and will ensure you have the best possible outcome.

It can be a big job, but this planning phase is so worth it

By now you know where you’re going and when you’re going; and you have a rough idea of what your adventure is going to look like. High Five!

The next step is working out your travel budget, ensuring you have enough savings to take this dream trip, and booking all the different elements of your holiday.
Who wants to talk about money, right?
But, unless you’re getting paid to travel, you do need to pay in order to travel.

Any Questions?

Comment below, or flick me an email if you have any questions about the planning phase of your holiday.
I am here to help, and there is no question too big or small -I’d love to hear from you!
And I’m sure someone else in the tribe will benefit from your response, too.

Pin it!

Planning your next Trip


Whistler_Zipline 2

Author: Michelle

Michelle Harvey is a kiwi traveller, writer, photographer, list-maker, coffee drinker, and wanderer. Winter holidays are her favourite kind.

Leave a Comment, or Subscribe to the blog