How to Book a Holiday


There’s a first time for everything, and booking a holiday is no different.

You might be reading this post because you’re looking to plan your first solo trip away. Maybe another family member usually books the annual hols and this is the first time you’ve found yourself taking the lead. Or perhaps you’ve decided you want to organise a surprise trip for someone special and you’re not sure where to start.

Whatever the reason you’re here, I’m writing this post so that you (hopefully) won’t find the internet quite as intimidating as it may first appear when you start approaching travel planning.

It’s a comprehensive guide that will ask you the questions you need to answer in order to determine which type of trip best suits your needs, before directing you towards the websites that will help you to put plans in place.

I’m about to tell you pretty much all I know about how to book holidays! I hope it helps.

Now let’s start with those questions…


Where would you like to go?

If you’re booking for a group of people, like extended family, you may already have an idea of where you all want to go. But sometimes, when the world is your oyster, things can get a little overwhelming. Go with your gut and write down a few places you’d like to see and visit.

Only you know where you’d like to go, but if you’re having trouble deciding, ask yourself what’s most up your street – a city break, beach holiday or adventure travel trip. These aren’t definitive categories by any means, but they’ll help you narrow down your options.

TOP TIP: For endless city break ideas, you can’t really go wrong with Europe. Remember though, to think beyond the obvious if you want more value for money. Try looking east rather than west for a real bargain. (Gdansk in Poland, Ljubljana in Slovenia and Zadar in Croatia are all on my radar for future trips.)


When can you travel?

For many of us (hey, married to a teacher here!), travelling during peak season and having to suffer the inevitable price hikes is a necessary evil. If you find yourself having to follow the pattern of school holidays, remember it pays to book early.

You’re competing with the masses for the best deals here, so although it’s certainly possible to bag a last minute bargain, be mindful that your choices may be a lot more limited when you leave it late, and you’re much more likely to have to compromise on something, whether that’s distance to the beach, to having to choose another town entirely on the Greek island you fancy, for example.

TOP TIP: If you can manage it, travel in the shoulder season, or completely out of season. Try Paris just after Christmas in winter when there’s still too much of a chill to entice the crowds. Or visit Italy in Autumn when the wave of summer visitors has been and gone.


How long have you got?

Fancy visiting Australia but only have a week’s annual leave left to take? Now might not be the best moment. Think about flight times and the possibility of jet lag when you only have a short window in which to travel.

Don’t lose too much of your holiday time in transit if you can only manage a short break. So if a long weekend is all you have to spare, maybe consider anything up to and including a three hour flight. Any longer than that might just be asking too much.

TOP TIP: Don’t assume you need to write off the last day of your hols waiting around if you have a late flight home. Often, hotels will be able to offer a courtesy room for you to shower in after you’ve already checked out and they nearly always allow you to store your luggage.

If you’re self catering or in a B&B this might not always be possible, but make sure you drop your accommodation an email to check. Then you can really treat your last day as part of your trip rather than just a wasted day of waiting.

airport (2)

What’s your budget?

The further you go, the more expensive it’s likely to be, so you should think realistically about what you can spend before you set your heart on any particular holiday. Often, this is what will play a significant part in helping you to decide where you can actually afford to go and what sort of accommodation you can afford to stay in.

It’s very easy to get a shock when you start plugging dates and destinations into a booking website as their “recommended” choices are what usually pop up first, and prices can be all over the place.

Be wary and remember to filter and order the list that gets churned out to suit your own preferences. Play about. Maybe look at hotels only to begin with, and if they prove too pricey, filter them out in favour of B&B’s and self catering apartments.

Also, know where to look for sites that pride themselves on flash sales (deals that are only available for a limited time). You could find something that buys you a lot more luxury bang for your buck, but you have to be prepared to book it when you see it.

He who hesitates is lost in this game – and I’ve learned that from experience.

TOP TIP: Set up an email address that you’ll use purely for signing up to receive deals from travel sites. Depending on the site, you can usually opt in to news about sales, deals related to shortlisted destinations, or price alerts for specific routes you want to watch.


Independent travel or package holiday (and what’s the difference)?

In a nutshell, booking independent travel means you arrange your flights, accommodation and any transfer journeys (trains, taxis, buses etc.) separately.

You could book flights directly on an airline website, accommodation through a different service (or directly with the place you choose) and any onward travel through local transport websites (or just research a route and pay when you’re away). Doing it this way can save you a lot of money, but it can take longer to search for deals on the separate bits of your trip.

An alternative is a package holiday – where everything is covered in one booking, usually including transfers from the airport to wherever you stay and a company representative in your destination who you can easily contact in person to assist you.

You can easily book packages yourself online, and there are often deals and sales to take advantage of, but it usually does end up costing more than independent booking and you may find it more difficult to travel “of the beaten path” as package holiday destinations are usually places with mass appeal.

However, in the UK, if you book a package with ATOL protection, you can rest easy knowing that should the company you book with go bust before or while you’re away (it does happen, unfortunately), you’ll either get your money back, or be brought home. Independent travel plans are not covered in the same way. Remember though, good insurance is a necessity no matter how you choose to book.

TOP TIP: I always book my city breaks and long weekends independently, and usually book one big beach holiday a year as a package so it’s completely hassle free.


Once you’ve done your research, hopefully you have some idea where you want to go and when, along with how long for and how much you’re willing to spend, so it’s time to get searching.

Here’s a list of resources and booking sites to get you going:

(all of these are my recommendations and none are sponsored links)

holiday pool

For Package Holidays:

There are lots of package holiday companies out there. I prefer to book with brands I know – but just check for ATOL protection before you book and your plans should be safe.


Thomson Holidays

Thomas Cook

(I currently have holidays booked with Thomson and Jet2Holidays for later in 2017)


For Independent Travel:

Flight bookings:

Google Flights


Both give an overview of who flies where and for how much. I love Skyscanner’s search everywhere facility to find me the cheapest destinations I can get to within my travel date window.

When I find something promising, I then price up the route on the airline’s own website, always checking if it’s cheaper to book two single flights with different airlines rather than a return ticket with one.

For cheap flights in Europe, I usually end up booking with one of these:





hotel hallway

For Accommodation



Alpharooms and are two of my favourites, and Trivago is great for comparing deals available on several sites. has a loyalty programme that can unlock discounts and perks when you book with them several times – I like this and I find their app great for filtering to find exactly what I want, and so easy to use.

Life tends to be a bit more unpredictable for me now, so I often choose a pay when you stay rate rather than a cheaper non refundable rate in case I need to cancel. It also means I get the safety net of having something booked, but I can still keep looking right up until the day before I travel for a better deal and then go and cancel my original booking if I find something.

For Flash Sales:

Secret Escapes

Voyage Prive

Both offer hotel only/ flight & hotel and package holiday options, but each offer is only open for a limited time. Sign up for emails and just keep checking – I bagged a great fancy hotel in Amsterdam for a brilliant price on Voyage Prive.

For Adventure Travel/Solo Trips:

Intrepid Travel

G Adventures

These are two tour companies I see alot online that stand out, though admittedly this style of travel isn’t my cup of tea. I’m not ashamed to say that my middle name is not adventure!

There are also experienced bloggers who run their own tours. Two worth checking out are:

Helen in Wonderlust

Wandering Earl


And a word about reviews:

One of the top resources for travel and holiday planning has to be Trip Advisor. It can be a great tool, but you have to know how to use it. Fake reviews are an issue these days, and they can be hard to spot sometimes.

Your best bet is to look overall scores. If you take an overview and accept that there will be someone who has had a bad experience pretty much everywhere, you can avoid getting into a situation that sees you afraid to book anything.

I always go for something high scoring (4 out of 5), with high numbers of reviews (unless it’s new accommodation that won’t have had loads of visitors yet). I then check out the bad reviews for anything that could be a problem for me.

Take an example of simple self catering accommodation in Greece – a bad review might suggest hard beds, or a lack of a flat screen TV (I’ve seen this type of complaint often). But these are not problems for me at all, and I can dismiss them right away. That’s what you’re looking to check for – whether someone else’s holiday hell is actually a genuine deal breaker for you, or not.

And beware of the odd wildly awful review among stuff that’s mostly good – they scream paid faker in my opinion, especially if the reviewer hasn’t submitted many other offerings to the site.

Similarly, something too good to be true from someone who doesn’t appear to have written many reviews can also be suspicious. Just be mindful that this stuff goes on and you should be ok.


So what do you think? Have I missed anything you’d still like to know about? Let me know in the comments, get in touch by email, or find me on Facebook, Instagram, and Twitter.

I hope you’ll get looking and get booking! But remember the world still has travel agents if all the internet leg work is not for you. And there’s absolutely nothing wrong with that.

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