Planning a Holiday: From Start to Finish

Holiday planning guide flatlay

Planning a holiday is one of my favourite pass times, but if you don’t know where to start it can all feel very overwhelming- after all the world is our oyster! As I work in the travel industry and love travelling (lets forget for a moment that I don’t get to travel nearly as much as I would like too!) I thought I’d help you map out the holiday planning process. Obviously depending on which destination you end up choosing, you might cut this planning part short as there isn’t much to plan and do besides unwind in a beach destination like Mauritius. But if you find yourself overwhelmed with options, here is how I usually narrow it down and get shiz done.

Type of Holiday

I always say that this is the best starting place as this ultimately informs your destination choice. You might like the idea of both a beach holiday and a cultural experience, which could lead you to looking at destinations which offer a little bit of both. Or you might choose to go somewhere for its natural beauty, which would likely cancel out a big city. You might like to combine a few of these and look for a single destination that offers all you’d like to do or plan a multi-city trip to cover a few of the things you like.


This could be one of the most overwhelming choices to make, but I think it is also one of the most enjoyable! With proper research, you really can’t make a wrong choice. This is where I’d say you should hit your Pinterest boards! If you’re anything like me, you’ll have a travel board or even a scrapbook filled to the brim with destinations you find incredibly attractive! But since there are some incredibly talented photographers out there, beautiful pictures are only the beginning.

My husband and I are both very privileged to get to travel for work (one more than the other) and we often choose to combine business trips with a leisure holiday (I hate the term bleisure, but that is essentially what we do). This means you not only save on cost but time as well (really important if you have limited leave days, since that 38 hours you spent travelling to and from your destination will be covered during your regular work hours).

This does however mean that we often to have to plan trips within a short period of time and we don’t necessarily get to go during the best season, but I still apply this process when planning on adding to a work trip.

It also brings me to my next point, if you can only take leave during a certain period of the year or plan on leaving within a set time frame then you need to take this into account which seasons your’e looking at when choosing the destination.

I find it helps having a kind of a travel bucket list, destinations that I’ve always dreamt of going to! Mine looks something like this:

  • Paris
  • Rome
  • Florence & Tuscany
  • Croatia (Islands & Inland)
  • Amalfi / Cinque Terre / Capri
  • London (and surrounds)
  • Greater France (Carcassone, Champagne Region, Southern Coast, Grasse, etc)
  • New York
  • Prague
  • Portugal
  • Turkey
  • Germany Christmas markets & Castles
  • Italian lake districts
  • Greece (Santorini & other islands)
  • Iceland
  • Spain
  • Morocco

As you can  see it is quite extensive though not complete. I’ve ticked off places I’ve already visited, not because I don’t want to return, but because the world is too small to see the same place twice if I haven’t at least ticked off some of the rest of my list.

You might wonder how I’ve settled on this list so that you can get started on your own (which might look very similar or completely different, I kind of love knowing which destinations are on other’s lists!)? I’ve ranked my list from places I’d like to visit the most – as in I can’t imagine not seeing within the next few years – to places I’d love to visit if given the chance. There is obviously so much more I’d like to see, but I don’t feel I should spend my money on visiting elsewhere if that might mean I’m spending money which I could save for elsewhere on the list.

Paris is an obvious choice to me, I went as a child and loved it and desperately want to show my husband and experience it all properly as an adult. It is hard to say why it is at the top of my list as I’ve just always wanted to go – it is a combination of the delicious food, beautiful architecture, history, art and of course the window shopping. Paris and Italy were always at the top of my list!

Croatia is a more recent addition, as I first read an article on some of the islands about four years ago and have been dreaming about it ever since! I love to swim, but appreciate beautiful architecture and history even more – making Croatia the perfect combo for me. Some of my colleagues have been and everything they say about it seems so magical and perfect, plus I keep falling in love with pictures of Croatia all over each time I see it. For me that is key, it is not just one blogger or article that has convinced me I want to go. I’ve based this on feedback from people I know that paid for their own trip, on pictures they took on phones that still look breathtaking and on doing a little research about the country. So often, I find people get swayed by what their friends say or a blogger said.


Surprisingly budget didn’t make it to the top of the list hey? I find that most destinations can be adjusted to suit your budget if you’re willing to sacrifice a little. I think it is a good idea to start at the top of your list and see whether you can afford to go to that destination with your current budget, and if you had to make cuts whether these would significantly influence whether you’d enjoy the holiday.

Say you could afford to go to Paris but couldn’t afford a 5 Michelin star meal which has always been on your bucket list it might be worth taking a step back – do you realistically think if you waited a few years you would then be able to afford it? Would your budget be enough to cover your dream holiday to another destination high on your list? Basically it all comes down to prioritising.

I usually make a list of estimated prices for flights, daily accommodation rates (AirBnB is amazing), estimated daily food budgets and the price of all non-negotiable activities I’d like to do. This helps me get a realistic idea of pricing, but pricing can change drastically the longer you wait to book. So I’d say at this stage you should decide whether you’re going ahead with the planning process or not. You might find yourself going back to your list and starting from scratch – nothing wrong with that.


I usually make a Google Spreadsheet that I can share with my co-travellers and then start mapping out my holiday, starting with places I’d like to see, things I want to do and areas I’d like to explore.

Whilst you’ll likely find a tonne of blog posts about your chosen destination, I usually like starting with a guidebook. I know the recommendations can often be slightly outdated or very touristy, but I love getting a general overview of a country or city before I delve into more detail-oriented blog posts. I also love reading about the history of each destination to get a real appreciation of it.

As I go along, I add activities, places I’d like to visit and things to see or do to my Google spreadsheet. Basically this could be anything like pop into the Laduree shop on x street, visit the Louvre or picnic along the Seinne. The things I can’t imagine not doing when in that specific country.

Then taking a map (Google maps will do, although I do prefer a printed version) I go through my list, double check everything on it, add the estimated cost (for tickets and transport), organise it according to activities that can be done on a single day and then add a pin on the map to where it has to be done. You might soon see clusters emerge or notice that something a little further away is the only activity you want to do in that area and re-evaluate.

If you’re doing this with a country like Italy that is incredibly vast, you might need to split it into two trips (depending on the time frame or budget you have available).

Creating your map also helps narrow down the area you should stay in. It is something I struggle with most as there are so many factors to take into account – affordability, availability, close to a metro stop, close to affordable restaurants, close to sites you want to see and generally a safe area – even at night.

With this map at hand, I’ll tackle accommodation sites. If you’re on a budget, I can’t recommend an AirBnB apartment enough! Be sure to check the reviews, but generally there are some amazing places available at a fraction of the cost of a hotel and with a kitchen you can choose to prepare lunch or breakfast at home if the budget is tight. I actually like preparing meals with fresh produce bought from markets and local delis, as it really makes it feel like you’re living there.

On AirBnB I’ll add all my parameters (price, occupants, number of rooms, etc) and then save a number of places that look good to a city-specific Wishlist. That way it is easy to come back and make a booking when the time is right.

Calculating Your stay

Now that all your research is done, you should calculate the estimated stay at each of your stops according to the planned activities. I’ll always advise you to add at least one or two days without tiring activities like museum visits so that you can simply wander and explore. Often those days create the best memories!

There is no rule on how long you should go away for, but I feel like I get the best value for money out of a 14 day stay as flights often take a large chunk of the budget.

Make A Rough Itinerary & Booking The Biggies

You should already have a rough itinerary from the above, but perhaps it needs some organising. Now is also the time to decide how you are going to get to different cities or countries if that is necessary – trains, flights or car hire.

If you haven’t already decided on specific dates that you need to be somewhere, you can play around with flight dates on an online booking engine to find the cheapest flights. Mid-week flights are the best for budget-conscious travellers – I always find the cheapest flights on Tuesdays and Thursdays.

When your dates are set in stone, you can go back to the Wishlists you created on websites like AirBnB and and see what is available on your travel dates. When making that final choice, I like dropping a pin on a Google map close to the hotel or apartment to check what the surrounding area looks like. Even a centrally located spot could look slightly dodgy, with dilapidated buildings and spray paint often being the biggest warning signs. I look out for local shops, cafes, restaurants and other reputable hotels as good signs. Obviously there are exceptions to these guidelines, but I feel like they are a good place to start when sussing out an unknown neighourhood.

If you are happy with your itinerary, you can book your flights, accommodation and activities. If you are still a little unsure, you might choose to book this in stages starting with your international flights and the first few nights stay and then book the rest when you feel settled on your itinerary – as changes to a booking might be very expensive or in some cases not even possible. The only threat here is price increases and availability.

Also be sure to make all visa bookings as soon as possible if necessary and check whether you require any additional documents (UBC or Yellow Fever certificates come to mind!).

Beef Out Your Itinerary & Lock Down Any Uncertainties

Booking all of the above can be slightly stressful, but once it is over it should be plain sailing until you reach your holiday destination! I like to take this time and amp myself up even more for my visit by reading as much as possible about the places I am visiting, watching vlogs about the destination and browsing Instagram accounts using the relevant hashtags and locations.

This might also be the perfect time to find a few restaurant recommendations, make a shopping list, figure out the local train/tram or underground set-up and plan how you’ll get from the airport to your hotel. You’ll want to leave room to stumble upon a magical place all on your own, but I like having a backup plan in case nothing you see inspires you.

This was quite a beefy post, but I loved writing this and hope it helps you if you are even remotely unsure of where to begin when planning a holiday! As I mentioned above, I’d love to know which travel destinations are on your lists (both local and international)! So please share that as well as any other handy travel tips.


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