Girl planning her dream holidays

How to Plan Your Dream Holidays – A Step by Step Guide

Planning your dream holidays can be daunting if you don’t know how to start. I used to spend hours and hours researching places and looking for the best accommodations and flight prices.

It could easily take me a week to plan every single thing! 

After my 7 am to 3 pm work, I used to arrive home, prepare a strong black tea to keep me going and spend the rest of my afternoon and evening checking flights and ending up on page 15 of Booking.com.

However, after many years of travelling around Europe and other parts of the world, I finally cracked the code on how to plan my dream holidays faster and easier than even my travel planner can.

I’m no longer spending a week planning my holidays. Instead, I’m doing it in half the time and I’m no longer overwhelmed by so much information out there! 

I want you to spend less time researching and more time enjoying. I want you to have the holidays you’ve always dreamed of!

The holidays that you’ve been thinking about for a long time, that you’ve kept checking prices for, that have made you excited every time you heard the destination, that you’ve continued to find pictures of on Instagram and thought, “I wish I was there!”

Read on for 10 steps that I follow every time I want to plan my next trip so you can implement them straight away. 

dream holidays

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10 Steps to Plan Your Dream Holidays

1. Make a list of the places you want to visit

First thing’s first! Start by thinking of places you want to visit. If you look at your budget first, you’ll automatically look at the cheapest options, and this is one of the reasons I don’t look at the budget yet. 

Take a pen and notebook and just write all those places you’ve dreamed of! Or if you’re a techie, you can also open a Google Drive document or Excel to add all these dream places to go.

Don’t think about how many you’re writing or other aspects of your trip yet!

If you have places in mind but you’re unsure if you really want to visit them, have a quick look at step 8 – “Explore activities and tour options for things to do.” 

If you’re very clear on this, just grab your ultimate travel bucket list and check the next step.

blue lagoon

2. Set a budget and a duration

Who doesn’t want to travel as cheap as possible? Think about how much money you’d like to spend on your holidays, considering the length of them.

Travelling as cheap as possible not only allows you to have more pocket money for activities or souvenirs during your holidays, but it’ll allow you to take another trip later on or to pay off that student debt. 

If one of your dream destinations is expensive, go through your monthly expenses (rent, food, meals out, clothes, etc.) and look if you could and would be willing to sacrifice something.

For example, I stopped spending money on matcha and chai lattes in Starbucks every week and I put that money towards my holidays. Believe it or not, I used to go twice a week and I was spending 12 pounds in Starbucks (that was 48 pounds every single month!)

Since then, I’ve been able to save for a weekend in London to attend a beauty event in the Saatchi Gallery or for day trips around the UK.

You don’t need to save lots every week, it could be anything from 5 pounds or euros to 20. 

You can put it in a money box or set up a savings account. This money can be for anything really: flights, accommodation, food, activities, etc.

I normally travel with my partner, so we like putting the money in the money box every week and it’s amazing! You get more excited to save for your next adventure and it makes you realise that small amounts can result in a decent amount to spend on food or flights. 

This will help you make your dream holidays happen.

3. Decide what you want from your dream holidays 

Grab your notebook or open a Word/Excel document on your laptop and look at all the places you’ve written down on your list.

While you read over these places, start asking yourself, “what type of holidays do I actually want to have?” and write down your preferences on a sticky note to compare them with your list of places. This exercise will help you choose the places according to what you really want.

For example, if you’re looking for adventure, you should choose to go to Indonesia and surf the big waves or go paragliding in South Africa to see stunning landscapes. Or if you’re looking for somewhere hot and close to Europe, you could go see picturesque colourful houses in Portugal or stunning mosaic work in Barcelona

palau de la musica

Also, if you’ve written down many nordic destinations (i.e. Finland, Norway, etc.) it can mean that you prefer colder places where you can enjoy the snow or the lakes and mountains.

By deciding what you want from your holidays, you can determine whether you want an all-inclusive holiday or you prefer to look for your own flight and accommodation.

If you’re planning to travel for a longer period (i.e. more than a month) you can also decide if you’d like to visit other destinations. 

Also, do you want to travel solo, with your partner/family or with a group of friends? This will definitely make your experience different!

4. Choose three places from your list

After setting your preferences, choose your top three destinations. This way you can compare different options if you’re still unsure where you want to go.

5. Look for flight prices

The trickiest part! You could spend hours or even days looking for the best price, so I want you to be aware of some myths: 

  1. Flights are always cheaper on Tuesdays.
  2. You can always get the best price if you buy a last-minute ticket. 

Both are FALSE!

Best travel apps for Europe

You can’t predict the future and you can’t do much about flight prices because you may book a ticket now and there’s a special offer for the same ticket tomorrow!

Don’t stress about flight prices, I’ve done this before and guess what? I waited longer and ended up buying a ticket which was more expensive than before.

I always look at Kayak, Skyscanner, Google flights and then compare them to the airline websites.

This way you have different options to compare and choose the best one. There are times when you’ll find it is cheaper to book with the airlines rather than these travel search engines and vice versa. 

Tips for booking your flights

  • Be flexible with dates and times to get a better fare.
  • If you’re travelling with others, look for a single ticket and then add the others (it’ll be cheaper than getting two people from the first time.)
  • Clear your browser cache when looking at a flight several times.

6. Look for accommodation

I remember a friend booked accommodation for us and we ended up in a room that didn’t look like the pictures she saw at all. The room was small and not as clean as we’d have liked it (we even found a cockroach!)

There’s nothing worse than ending up in a place you don’t like! Since then, I have always double-checked what others are planning to book. But, I normally like planning my trip myself.

First, choose what type of accommodation you’d like to stay in. Would you like to stay in a hotel or in a villa?

lobby at york principal

For hotels, I always look at Booking.com and Expedia. You’ll find good deals on these websites and they both have rewards you can take advantage of.

For houses and villas, I recommend using Airbnb because they have a great variety of houses/villas you can choose from.

Also, if you’re looking for something luxurious, they’ve introduced “Airbnb Luxe” which includes houses/apartments and villas with infinity pools, indoor cinemas, and many more incredible features.

If you’re travelling solo and you’d love to meet new people, you can stay in a hostel and use HostelWorld to book your accommodation.

Alternatively, you can use Couchsurfing! It’s a great way to meet locals if you’re looking for an authentic experience.

If you want to go all-inclusive, I check big companies such as TUI and Virgin Holidays (to travel from Europe to America) and compare with other websites such as Holiday Pirates.

Also, check your accommodation ratings and compare prices with TripAdvisor too. 

7. Continue crossing out some of your places 

After looking for flight and accommodation for your three chosen places, it’s time you make a decision

Hopefully, you already know where to go, but if not, cross out another option so this leaves you with two options to choose from.

You may cross out a destination because hotels or flights are way too expensive, you’ve found out that a particular destination is better for the time you want to travel, or just you didn’t feel as excited as before!

Don’t worry, you can decide on your dream destination after exploring the activities in the next section.

8. Explore activities and tour options

You probably have an idea of what you want to do but you can look on Tripadvisor and other websites such as Lonely Planet, Travel + Leisure, etc. for a general idea of things you can do in your destination.

If you want something more personalised or authentic, you can use Pinterest as a search engine to lead you to other people’s blogs talking about your destination and their suggestions and, save pins to your boards.

You can also open Google Maps and create a list for your trip. Include all the places you want to visit, so you don’t need to look for addresses later. 

If you’ve never created a list: 

1) Go to Google Maps

2) Click on the menu (the three lines on the left-hand side)

3) Select “places”

4) Click on “saved” and the blue bottom to create a list

5) Name the list and start adding places. You can also share your list with others and print the map.

📌 For tour options, you can either look at Airbnb Experiences or Get Your Guide. I especially like Get Your Guide because there are plenty of authentic and local experiences you can do.

palma de mallorca cathedral

9. Get travel insurance

If you don’t want to worry about what would happen if you lost your luggage or got sick, or there was a pandemic, you should get travel insurance.

If you’re a European citizen, you can apply for the European Health Insurance Card (EHIC) which is free! This covers you for temporary stays in hospitals at a reduced cost anywhere in Europe. However, this would not cover you if, say, you need a mountain rescue at a ski resort, because of the high cost!

This is why is important to have both the EHIC and travel insurance despite belonging to the European Union.

Travel insurance becomes even more important if you’re travelling outside of Europe because you won’t be covered at all. Travel insurance covers you for many things such as loss of luggage, flight delays (depending on the delay and insurance company), accidents, etc. It’s peace of mind in any situation! 

Imagine you’re taking your latest camera and all the expensive accessories, and your luggage gets lost by the airline company. Your travel insurance will compensate you for them. 

Before buying any insurance, please check what is covered and what isn’t. For example, some insurances may not cover you if you have a pre-existing illness or only covers you in certain cases.

You don’t have to buy annual travel insurance if you aren’t planning to travel much. You can simply buy one for your 7 day road trip to Andalucia, for example. 

Making a claim is very simple and quick! In most cases, you have to sign in to their website, complete a small survey and attach documents to support the claim.

That’s why I recommend saving all your tickets from transport, food, accommodation, doctor, etc. The insurance company will ask you for these types of documents to support your claim.

There are many websites to check insurance but WorldNomads is well-known for being one of the best travel insurances, especially for long trips.

10. Create your own itinerary

This is totally up to you, but if you love organizing your trips, it’s one of the most exciting parts!

If you’re going for a short trip and want to make the most of it, I would recommend doing a daily plan. Nevertheless, leave some time without any plans and travel with the flow.

For example, I visited New York for 5 days, so, before my trip, I planned every single day to make sure I saw everything I wanted. But there were a couple of times I didn’t have a plan because I wanted to be present and be surprised by unexpected beautiful places such as the High Line area or some street art near 3rd Avenue.

However, if you’re planning to stay over three weeks somewhere, I’d recommend doing a simple weekly plan since you have more time to explore the destination and you can spread different activities across the days.

You can open a word document or google drive document (so you can access it anytime from your phone) and create a table entering the day of the week. You can start filling in the table with your activities and add times if you’ve booked something you have to attend at a specific time.

I understand you want everything to go well because I’m the same way! But, don’t stress! Enjoy planning your holidays and, REMINDER! You don’t have to plan every single aspect of your trip because things can change.

Maybe you think you’ll spend 3 weeks in Australia but then you end up falling in love with the place and want to stay longer. Maybe you don’t like it because it doesn’t meet your expectations and you want to leave sooner!

Be flexible with changes because they’re part of the travel experience. 


If you want an authentic travel experience when you visit other places, go and download The Ultimate Guide to Travel Like a Local Wherever You Go for simple tips you can implement straight away.

Do you have any questions about planning a trip? Email me or send me a DM on Instagram. I’d be very happy to help you plan your dream holiday.

Enjoy our holiday!

Cristina x

P.S. Don’t forget to share it with your loved ones 😊

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