how to plan an itinerary

How To Plan An Itinerary Step By Step

Planning an itinerary is never easy.

You have to find accommodation, transportation, a good destination, activities or sightseeing options… The list can be almost endless!

It looks even harder when you don’t have a clue where to start looking! The internet is huge right?

If you’re a bit like me you always try to find unique places to stay and unique experiences. Therefore, you might not be satisfied with a ‘regular’ hotel.

This however, makes booking a trip even more difficult than it already is.

This is why I decided to help you and share all my travel resources and action plans on how to plan an itinerary for your next trip!

After reading this you’ll:

  • find more inspiration for your next trips
  • know where to start looking on the internet
  • be able to save tons of time
  • find a more unique place
  • know exactly how to find the best activities/sightseeing

Say goodbye to endless internet searches!

Ready? Here is how to plan for an itinerary!

Download the FREE planning your trip made easy workbook here

How to plan an itinerary: start here!

Finding a destination

world map
Photo by Adolfo Félix on Unsplash

First things first, your destination.

The first step in planning your itinerary will be deciding on your dream destination! Where would you like to go?

The unstructured way for finding inspiration

Sometimes, you’ll have a fixed place in mind, but other times you’ll have no clue where to go.

If you are in the completely clueless stage I suggest opening Google Maps and starting to explore the world! Zoom in on destinations you like and click on cities. You’ll find basic information like weather, photo’s and hotel suggestions there.

Another option is to start exploring travel blogs like this one. These often contain personal experiences so you’ll know what to expect.

What I once did was walking into a bookstore and blindly picking a travel guide! The travel guide I picked was going to be the destination I would go to.

Another thing I like to do is visit the website ‘Voyage Privée‘. If you make a (free) account on this website you have access to hundreds of deals, mainly for resorts.

The website offers you unseen discounts but I have never booked anything myself. However, I use this website to get some inspiration on lovely destinations and sometimes unique accommodations.

The structured way for picking a destination

Of course, you might want to do this a bit more structured.

Try to imagine how your ideal destination would look like. What activities would you like to do there? How is the weather? How long do you want to travel? Do you like planes? Should it be remote or do you like vibrant cities?

Try to pick a few destinations that qualify your criteria and list up the pros and cons: how is the weather? Are there a lot of tourists? What can you do there? What is the best time to visit that destination? Which features does the destination have that you are looking for?

By having a clear idea of what kind of vacation you want before you start looking, the process of deciding on a destination will save you tons of time!

Difficult to choose? Read the post where I go more in-depth on choosing a destination!

Picking a date

agenda - how to plan an itinerary
Photo by Essentialiving

Once you’ve decided on your destination, you can try to pick a date. Always take the best time to visit your specific destination into account! For example, when you plan a trip to South Africa, you might not want to go there in August since it will be middle of winter there!

I always try to pick a two-week span so I can pick my specific dates according to the cheapest dates of the airline/transportation companies and accommodations.

If you’re trying to decide on a fixed date it is wise to look at those airfares or train fares as well as the price of accommodation.

Usually, I start looking online at flights on the website of Skyscanner and for accommodation on Airbnb. This gives me a good overview of the cheapest dates so I can choose them accordingly!

Deciding on transportation

train ride
Photo by JK

You can decide whether to put accommodation or transportation first, but I usually start with transportation.

There are multiple options for transportation. For a far-away vacation, it might be obvious to book a flight, but if the destination is less than a 12-hour drive away I prefer driving.

Related: fun road trip questions to keep you entertained

The same reasoning goes for trains, but night-trains are becoming a thing again so this is certainly an option too for longer-distance destinations!

However, in my experience, trains are not the cheapest option but it can certainly be more relaxing and faster than waiting or stressing for a flight!

So choosing a way of transportation is merely a personal choice and depends on the distance as well.

Try to think about what would save you a lot of time and/or a lot of money. Even though flying goes faster, it doesn’t mean that the whole journey of arriving at the airport, waiting etc will be the fastest. Maybe you’re faster off by train?

Below you can find the websites I use to book my flights etc. I always use price comparison sites for my flights because they can ensure you the lowest price and I swear by Skyscanner because I always find the cheapest flights there!

Transportation resources



Deciding on accommodation

hotel with view - choose your ideal accommodation
Photo by Manuel Moreno

After picking a place, a date and your preferred transportation, it is time to look for accommodation!

Think about what kind of accommodation you want. Some people like all-in-resorts, others might like it very basic. Do you want a hotel? Hostel? B&B? Airbnb? Think about it.

I prefer to book Airbnbs because they are often the cheapest and they can be very charming! The hosts are also very friendly and I never had a bad experience with them!

Once you’ve decided on a type of accommodation it is key to search on the right websites.

If you prefer a hotel or B&B, the most common options are, Trivago, Expedia, Tripadvisor

I already told you that I’m a fan of Airbnb. Hosts rent you their home for short periods and take care of almost everything like you have it in a hotel. The only thing you have to provide yourself is food. However, some will offer breakfast as well.

Another option I like is house sitting. I never tried it myself but it ranks high on my bucket list! The concept is that you take care of someone else’s house and pets while they are away. In return, you don’t have to pay anything for the accommodation!

Sounds great right?

The most established website is Trusted Housesitters and of course, you can also find someone on that website who will look after your house and pets!

If you have experience with house sitting I would love to hear about your experience. Send me a message here!

For hostels in Europe, there is an amazing website Hostels Mania which gives you an overview of the best hostels in each country. But the biggest site for booking a room in a hostel is without doubt

What to do on your trip

Picking the right activities

Photo by Markus Spiske

If you have read the previous steps you have now found: a destination, a date, transportation and accommodation.

The question remains what exactly to do on your vacation?

I don’t need to tell you that you could simply start looking on google what there is to do. You are probably reading this because you’ve tried it before and it is very time-consuming.

I always start by looking at Tripadvisor. I used to use this app only for restaurants but they have a lot more to offer! On their website, you just have to type in your destination and you’ll be able to see the top things to do at that destination.

This is usually my starting point for deciding what to do, looking at the most popular destinations first!

Now that you have found the popular touristic spots, the second step is to look at the website of the destination’s touristic service. On their websites, you will find more time-related activities like festivals, theme days etc.

Of course, the most unique experiences are those without a crowd of tourists next to us! If you want to go off the typical touristic trail, the best thing you can do is ask a local for the best spots.

Many blogs can be found on the internet written by locals but I would also advise you to keep a free spot in your busy vacation schedule and just ask it in person to people you encounter on your trip. Whether it is the waitress in a restaurant or just someone passing by, they will know the truly unique spots!

Sometimes I decide to buy myself a (paper) travel guide. This was the case when I left for Canada, because the guide included multiple destinations, maps and gave me a handy, simple overview of everything there was to do.

Thus, if you don’t mind investing another 10 dollars, buying a travel guide for your destination is definitely the fastest option. I recommend it if you are visiting multiple cities/regions for a longer time.

All sorts of guides can be found on Amazon. I personally used Marco Polo’s pocket guide for East Canada because it is rather small, contains maps, an app for your phone and all the basic information you need!

Other popular travel guides are those of Lonely Planet but they offer way more than that. On their website, you can find destinations, hotels, car rentals, insurance etc.

Finding the best food spots!

The same tactics you use for finding the right activities can be used for finding the perfect dinner spot!

Start on Tripadvisor. They simply offer an overview of ALL the restaurants that can be found at any destination (for any meal). Moreover, all the restaurants get ratings and reviews from previous customers so you’ll know what to expect.

You can also find more authentic places on Tripadvisor (besides the obvious touristic restaurants) but I advise you again to ask locals about the best spot to eat. They will know where you can find the best food for a decent price (not the touristic price) and in the most authentic atmosphere!

I highly recommend asking this! The last thing you want is an over-expensive restaurant full of tourists, right?

How to find your way

My hero and my everything on a trip is GOOGLE MAPS. (Sorry for putting this in brackets but this is sooo important). So many of my trips have succeeded thanks to Google Maps!

I love my freedom on a trip and this involves finding my own way.

Google Maps has everything you need: a general map, a map of the public transport system as well as the hours of trams, buses, the subway, trains… everything. You can also download maps to use them offline.

Okay, I must confess that I’ve had blunders with Google Maps, but most of the time they are exactly right.

(Yes, my friends and I ended up in the middle of nowhere with a bike between the fields at a lake. It was so bad that a Spanish driver gave me his phone number in case we would not be able to return before dark.)

Most hotels also provide paper maps of the region and a lot of regions also have their own apps for this. You can go to the tourist office for more stuff about public transport etc.

What else?

passports - how to plan an itinerary
Photo by Jaimie Harmsen


You absolutely need insurance. It will cover you for so many risks you undertake during your trip (even if you don’t see them as risks).

Some people have their travel insurance included in their general (family) insurance. Others take out separate insurance for each trip.

What should certainly be included in your insurance?

  • cancellation of flights etc due to unforeseen circumstances
  • accidents abroad which lead to medical costs
  • repatriation in the case of a severe accident
  • coverage of dangerous activities e.g. scuba diving (if that’s on your bucket list)

All airlines will try to sell you insurance for a cancelled flight. It’s up to you to decide whether you’ll need it. If it’s a very cheap flight at a cheap moment, I personally don’t bother taking insurance for it.

But I had moments I almost missed my flight due to slow traffic, weather etc. Then, it is advisable to have insurance together with your flight.

Always check for additional insurance with your insurance provider!

Travel documents

Make sure that you have all your travel documents before you leave on your trip! Think about passports, visa, insurance documents, booking confirmations etc.

Whether you need a passport depends on where you are going. EU citizens don’t need a passport to travel throughout Europe, but they do need their ID card.

Likewise, whether you need a visa depends on the agreements your home country has with other countries. The best way to check this is to look it up on your host country’s embassy’s website.

Tips & Tricks

  • Book your trip well in advance for the best price
  • Don’t settle for the first thing you see, other websites will offer it for a better price!
  • It’s very easy to find all the tourist spots in the region. Expect to make some effort to find more unique places!

Ready to plan your itinerary?

Now, you should have all the essential information on how to plan an itinerary!

So what are you waiting for? Start planning your next trip!

Download my FREE workbook to start planning


Read my other posts for more information about travelling with low-cost airlines, how to travel without baggage (to save on baggage fees) or budget travel!

If you want to know more, check out my travel resources page!

2 thoughts on “How To Plan An Itinerary Step By Step”

  1. I’ve never used insurance for a trip before but you make a good case for it in this post! Plus with the world temporary norm (I refuse to call it “new norm”), it definitely swaying me to add for a trip I am still planning to Scotland this fall. Thanks for a great read.


    1. Thank you so much! It’s very tempting to not take insurance but you never know what will happen. It can be a lifesaver in case of a disaster!

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