15 questions to ask yourself before you start your holiday search

The crucial step everyone misses, that saves time, money and transforms your holiday experience.

Finding the right holiday can feel so overwhelming, trawling through endless options not really sure what you’re looking for, or whether its worth the money.

A recommendation can feel amazing but the truth is, to find YOUR dream holiday you have to get really clear on what YOU want and need from it. Your appetite for adventure, for dis/comfort, your non-negotiables on accommodation, the spaces and activities you find rejuvenating and crucially, what it is you and your family need a break from.

I’m building out some tools to help with the whole planning and booking process. To help families make the most of their time away and the memory making experiences we crave.

I would really love feedback on whether its helpful. You can leave a comment below or message me directly.

PART ONE is about zoning out the noise of social media (other people’s holidays), marketing (what we’re told a holiday should look like) and conditioning (what we think a holiday should look like).

Clarifying our needs and wants before starting a holiday search means we can be much focused (and efficient) in what we are looking for AND make sure we don’t waste a penny of the budget on things that aren’t really important.

The four Es.

For simplicity I’ve structured this around 4 Es:

• What we/our kids are looking to Escape from

• The dream Environment

• The Experiences

• The Essentials

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ESCAPE FROM

1. What are you looking to Escape from?

   1. Mentally (e.g the mental load, thinking about what to cook for dinner, making decisions….)

   2. Physically (e.g. sitting at a desk, car pooling, laundry…)

2. What do you kids need an Escape from?

   • Mentally (e.g. homework, friendship dynamics, routine, sameness…)

   • Physically (e.g. screens, supervision…)

     [ACTION write down or draw as much detail as comes to mind, you can also do this as a family]

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   EXPERIENCES

3. When do you / your kids feel your most relaxed/energised/playful?

4. When do you feel the most connected as a family?

5. When do your kids feel their happiest, truest selves?

6. Think about the best holiday you ever had, what

   made it so special?

   [ACTION: From this list, write down the top 3-4 things you want to experience on this holiday]

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   ENVIRONMENT

7. What kinds of spaces make you feel relaxed/energised/playful (e.g. weather, landscape - coastal/rural/city/mountains/water, people - lots/few, culture - familiar/new…]

8. What kind of environment does your family need to feel at ease? [e.g. consider safety, independence…]

   [ACTION: From this list, summarise or draw your ideal environment]

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   ESSENTIALS

9. What is your budget for this trip? (e.g.travel, accommodation, car hire, activities, food and drink)

10. How far / how are you prepared to travel?

11. Once there, do you want to move around or stay in one place? (e.g. Arrive and stay put / 2-3 places / Cover as much ground as possible)

12. How much time do want to think about logistics whilst you are away? For example…

    1. I like a challenge, an adventure its part of a fun holiday

    2. I can follow a plan, but don’t want to have to think too much whilst away

    3. Minimal, my brain needs a complete break.

13. What are your accommodation non-negotiables? For example…

    1. How many, if any meals would you like to be catered on site

    2. How many rooms / living space / cooking, laundry facilities / outdoor space, do you need? Or would you prefer to squeeze into one room in favour of location/resort amenities/conveniences.

    3. Do you need amenities and experiences to be walkabout or do you like to hire a car?

14. What role do you see the accommodation/resort playing? for example

    1. The main focus for the trip

    2. A relaxing place to decompress in the evenings after a day out

    3. Just a base to sleep.

15. What type of accommodation makes the most sense? for example

    1. A ‘destination resort’

    2. An activity based resort

    3. Self catered apartment or villa? Or cottage cluster

    4. Boutique hotel in a walkable location

    5. Campsite or lodge resort

    6. Or a combination of the above.

    [ACTION, write down as much detail as comes up from these questions and share with your family to get everyone on the same page.]

Hopefully this will give you a much clearer idea of what you are looking for. Next week I’ll share STEP TWO - how you can use this list to run an effective needs based search.

In the meantime I’d love to hear whether this is a useful starting point? Whether it helps inspire you and your family to design your own dream trip?

Please do also share below how you plan and any tips you have for simplifying the process.