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The Ultimate Guide on How to Plan and Book the Perfect Holiday (Stress-Free)

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Are you trying to plan the perfect holiday? If so, you’ll know it can be a stressful experience – saving money, travel arrangements, insurance bookings, even choosing your favourite swimming costume can be difficult.

Holiday planning might sound like hell to some people but with our stress-free guide, you will be able to plan and book your dream getaway like a pro.

Everyone has an idea of what their perfect holiday looks like, but the big question is, where on earth do you start?

What to do you want out of your holiday?

There are many reasons people go on holiday – escaping the daily grind, exploring different cultures, or to have special family bonding time.

These are all perfectly good reasons to go on holiday, but they all have different factors that make a holiday fit for you.


If you long to escape the hustle and bustle, then you need to focus on a relaxing and serene environment.

Perhaps you and your partner need to immerse yourself in complete relaxation and help you put your life in perspective and forget about all your cares.

The ideal place for this could be a countryside break or a luxurious beach holiday.

Being adventurous

Are you a thrill seeker? This could range from exploring different cultures or trying out new activities such as skydiving.

Depending on what you desire, you might have to travel further afield, but there’s no need to worry as this can be completely feasible if you know where to look (and we definitely do!).

There is nothing more thrilling than doing something new and out of your comfort zone.

Family bonding

With a busy lifestyle, it can be hard to juggle everything, after all, you’ve only got two hands. With so much going on, you must remember what is most important; family.

A family holiday is a wonderful opportunity to bond and enjoy new experiences together, especially if you have children.

There’s always plenty of things to do on a family holiday and there’s usually something for everyone to enjoy.

Staycation vs Holiday abroad

UK holiday

You may already know if you want to stay close to home or travel the big wide world. Both have their pros and cons and it depends on your personal situation. If you’re still undecided, here’s some help:



  • The UK is picturesque, from beaches to castles, to mountain ranges, churches, villages and much more.
  • The UK is in the top 10 most visited countries in the whole world.
  • Less travel time.
  • Fewer tickets, passports, restricted baggage.
  • Don’t need to convert currencies.
  • No need to rent a car.
  • Fantastic holiday parks available, great for families.


  • The UK has unpredictable weather.
  • Might feel too close to home.
  • Already know the culture.


Travelling Abroad


  • Warmer weather and potential sunshine.
  • Different cultures can be invigorating and exciting.
  • New experiences and foods.
  • Every place in the world is completely unique in its architecture, history and landscape, making every sightseeing trip great in its own way.


  • Long flight times not great for children.
  • Can be more expensive than a staycation.
  • Unfamiliar surroundings.
  • Language barriers.


Time to choose your destination

You may already have your heart set on a destination, after all, there are so many amazing places to visit in the world.

A big factor in this will be your budget. Long haul flights can bump the cost of your trip up significantly, compared to a European holiday. However, once you arrive the living costs may be cheaper depending on where you go.

Do some research, look for some summer holiday inspiration and come up with a few ideas. This should be the fun part, so don’t stress yourself out about it.

If you’ve decided on a staycation, do the same: research. There are so many amazing holiday hotspots in the UK that you’ve probably never visited before.

When is the best time to book?

Should you book early, or try to pick up a last-minute deal?

Our advice would be to book your holiday sooner rather than later. You can take advantage of early booking discounts and you can you can secure the dates you want.

Don’t leave things to chance as you may regret it.

It can be difficult to get the annual leave when you work in healthcare, so planning ahead and booking early is really important. Make sure you can have the time off before you book it.

Most importantly, before you book it, check for NHS discounts!

Package holidays

January sales are one of the best things about January. The January sales aren’t just exclusively for clothes and electronics, there are plenty deals on package holidays too.

Package holidays have many benefits; less hassle, all booked at the same time, and you can add extras, such as airport transfers.

There’s a fantastic range of package holiday deals and discounts available to Health Service Discounts members from the likes of TUI, First Choice, Jet2holidays, and EasyJet.

Booking flights and hotel separately

There are many benefits to booking your flights and accommodation separately too! There’s more freedom and you could even find a better deal. So, when should you book your flights?

The Evening Standard have reported findings from travel search engine Skyscanner that show January is the best time of year to book travel. Metro have concurred, with findings from Hipmunk, a cheap flights website, stating that “January is the most ‘cost-effective’ month for travellers.”


A great way to get the best out of your money is to use comparison websites like, Travel Supermarket, and compare flight prices.

NHS and healthcare staff can get great discounts on worldwide hotels, apartments and villas, at all the popular destinations.

There is also a wide range of offers on UK breaks available to NHS and healthcare staff, including:


When to go on holiday

Holiday Planning

If you have children, the school summer holidays might seem like an obvious choice. But generally, it’s more expensive.

Going on holiday in half term is usually cheaper than during the school summer break. If you don’t have much flexibility, make sure that you book early before the prices rise.

If you don’t have kids, and you have some flexibility, booking out of season usually means places are quieter and you can pick up some bargains.

Another thing to consider is choosing a weekday to arrive at your destination. It will likely be less expensive and you can have a quieter arrival with less stress.

Stress-free holiday planning

Holiday Planning

Holiday planning is essential if you want the ‘perfect holiday’. Some of the most common stress points when planning a holiday are:

  • Packing
  • When to leave home
  • Keeping children entertained
  • Money
  • Directions
  • Days out/activities
  • Eating out


To start, you need to decide what you want to do. If you are going for a week and have children, you need to make sure you make the most of it and keep them entertained.


Plan out your days

  • Grab a notepad and write down each day – morning afternoon, evening.
  • Research activities in the area.
  • Buy a travel guide or read blogs.
  • Sort the activities into each day.
  • Research places to eat and drink and use review sites (e.g. TripAdvisor).
  • Set a budget for each day so you don’t run out of money.
  • Explore the culture and try something new.


Depending on the type of holiday you’re going on, you will be doing different things.

For example, if you are going for a relaxing holiday you might not need to plan as many activities.

But on the other hand, if you want to be adventurous or have a family bonding experience you will need to do a bit more holiday planning.

  • Sightseeing – plan out the sights that you don’t want to miss, how to get there and ticket prices.
  • Beach holiday – see if there are any water sports activities, water parks are great fun, or enjoy some local seafood at an amazing restaurant.
  • Exploring – go for a long walk and take in the sights. A great way to experience a new place is to purposely get ‘lost’ and find your way back, taking in everything around you.
  • Try something new – experience the culture, go to a local show, eat where the locals eat.
  • Get active – bike riding, hiking, try a new sport.
  • Spend time with your family.
  • Take a day to relax – you’re on holiday after all!


What to pack

Packing can be one of the most stressful parts of holiday planning. Making sure that you don’t forget anything is hard. Start saving a little bit at a time. £20 a month will slowly build up and you will be able to fill your suitcase with new items.

Beach holiday

Bucket and spade, sun cream, sun hat, flip flops, beach towel, swimming costume, and snorkels.


Kids holiday

Films, books, teddy, and favourite toy.



Tent, sleeping mat, sleeping bag, pillows, stove, flashlight, BBQs, fire pit, and marshmallows.


Winter holiday

Jumpers, hats and scarf and gloves, wellies, coat, woolly socks, blankets, and hot chocolate.


The ultimate holiday planning checklist.

Useful links

Check your passport is valid and in date for your return to the UK.

Check the weather before you go to make sure your plans won’t be spoiled.

Print off/screenshot any maps you might need.

Check reviews of restaurants and activities before booking them.

Tips on saving money on a summer holiday


Your perfect holiday is out there and with some perfect holiday planning, it can be achieved.

Travelling, family, friends, food, and weather can be unpredictable and stressful at times, but being able to adapt to change when necessary certainly makes holidays a lot more enjoyable.

You can see a full list of all our Holiday Deals for NHS staff and healthcare workers on our website. Its free to become a HSD member and use our discounts. Sign up today!

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