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Travel Planning Hacks # 1

Updated: Aug 17, 2023


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"Where am I going for my next holiday? "


"What is the place that I must visit, before kicking the bucket? "


"Wow, that looks amazing! I have to visit one day!"



Have you ever had these thoughts? Or perhaps the urge to travel came from an ad on TV or social media?


They are always showing these colourful footage of blossoming flowers, medieval villages, someone soaking in the bath tub while it's snowing outside....


They do seem quite appealing, especially after a tired work day, rolling your eyes at the teens or screaming little ones, or staring at the ever-growing load of laundry and dishes.


Who doesn't want to have a breather away from the daily mundane?


No more cooking, tidying; no demanding stakeholders. Just dipping your toes in the tropical sea, exploring hidden alleyways or getting some fresh airs in the woods.


But hang on, how much leave have you got?


What about your cashflow? Mortgage repayment?


When's the next school holiday? It'll cost a fortune to travel with the family!


Reality hits, and the dream holiday bubble bursts.


It's true. Travelling is often associated with costs, packing, unpacking and all the logistical headaches.


On top of that, planning a holiday is a job itself. It takes times, diligence, experience.


There is a universe of information out there, how do you know what's right for you?


If you ever find yourself fantasising about a holiday, but just can't seem to make it happen, read on, we've put together the following five travel planning hacks for you.


They include exactly what you need to consider, plus a bunch of practical, verified tips that are drawn from our own experiences (some painful - but hey, no pain no gain).


The travel planning hacks will help you to map out a journey that's rewarding, leaving you energised, rather than needing another holiday for your last holiday.


As bespoke travel planners, we're dedicated to make it all about you, exploring what you want, and help you to make it happen.


Let's get started.




Hack # 1: Set your priority and travel goal



'Priority' and 'goal' might remind you of your job already, but they are important if you want to feel actualised or achieved - which is on top of the Maslow’s Hierarchy Of Needs - basically, what makes a person feel satisfied.


Priority = What's most important to you on this trip.


Follow your heart and listen to the first thing that comes in mind.


What makes you happy?


A few words might've popped up: family; a proposal and getting a "Yes!"; to relax; to indulge; to have a glass of champagne on the Eiffel Tower; to see Machu Picchu; be in the nature.


Congratulations if you already have the name of the place or some landmarks in mind. If your heart tells you Eiffel Tower is your must see regardless of rain or shine, absolutely go for it!


If you're not too sure about where to go, but words like 'to indulge' and 'do whatever pleases me' came up, careful there, these things are closely related to budget.


Money is not everything, but it is important.


If you wanted to feel whatever you want on your holiday, especially if you feel the daily mundane is choking you, then choosing the right destination is particularly important.


For example, some of the places in the world like Bergen in Norway, or Ayers Rock/Uluru in Australia are amongst the most beautiful places, yet the most expensive to travel.


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There's no doubt that simply by being there, these places will bring you a feeling of wow and joy, but if your objective was to 'indulge', you might feel a bit hand tight, or feel more stressed having to deal with post-holiday credit card bills.


Yes, nature is free but park fees, rental cars, accomodations and food are not,


One could travel to expensive places and spend smartly. We'll talk about money in the Hack 4, which will be released in a few days.


For the time being, let's get to know you better.


Another priority could be 'family', or to have a 'nice family time'.


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What does 'nice' mean? Does it mean the adults are happy but the kids are on their screens? If your priority evolves around your loved ones who are travelling with you, it's a good idea to have a chat about what they want, and get them involved in the planning.


Objectives = what are you trying to get out of this holiday?


What do you want to see, to eat, to listen to, to hear, to do/achieve?


What are the activities that you'd like to do? Any concerts, shows, exhibitions?


Any plants/flower viewing seasons? Food or drinks that you'd like to taste?


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If you had a 'new year resolution', you could also align your travel plan with it.

For example, if your NYR was to keep fit, or lose your love handle, you could slot in some physical activities like hiking, kayaking, bush walking, swimming in your holiday planning.


Travel planning can be a fun process to get to know yourself better. Once you've thought about your priorities and travel objectives, you'll be able to start narrowing down your destinations,.


This, leads us to the second most important Travel hack: Timing is Everything.


Stay tuned and we'll see you tomorrow!




Author: Founder, Should Have Asked - Your Bespoke Travel.

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Michelle is an experienced researcher, design-thinker and in former life, government policy maker. Most days she’s an addicted traveller, a shower-soprano and mom of 30+ avocado trees.


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