How To Write An Itinerary For a 3-Week Trip

Do you only have three weeks for your upcoming holiday? If so, I’m sure you want to make the most out of it and hope for a smooth and memorable vacation. Before you get to this task, I know it’s been a long process; request time off from work, choose the destination and maybe even checked with your family and friends who might want to join you.

Writing an itinerary is actually not that hard, however, it takes some time to finish and most likely will take you a few drafts. Now, you don’t need to plan everything up to the smallest detail, although I do understand those who want to.

Making an itinerary shouldn’t stress you out or take so much of your time. It should be enjoyable, inspiring, and make you excited about the upcoming trip. However, if you haven’t done this before or you’re going with a friend or family you’ve never travelled with before, it takes a bit of patience.

Today, we’ll talk about how to write an itinerary, I’ll walk you through an easy guide for preparing and organising your 3-week holiday. This post is best for those who want to plan 70% of their trip, while travellers who like to wing it, feel free to read through, who knows, maybe you’ll find some cool tips.



Here is a little guide on what you need to remember on how to write an itinerary. This will give you an idea of what to look out for, prepare, remember, and most importantly, the best time to book the flights, accommodations, and tours, and most importantly, what’s the most comfortable way to travel for yourself.

The season and destination

This varies for many travellers. Depends on your free time, budget, activities you want to do, and your travel companions. The season will also dictate what you need to pack for a 3-week vacation.

The best way to determine when to go is to obviously ask when is your free time and/or your friends/family who are coming with you. Next is the tours you want to do in case they are “season” related like skiing, beach holiday, etc.

Of course, you have to make the decision where you want to go. Let’s say you want to go skiing in Europe. While that’s a fabulous idea, remember not to align your schedule for Christmas or New Year. These are super busy seasons, prices spike up, accommodations get snatched quickly, and well, the crowd.

If you really want to ski in Europe during winter, perhaps you can avoid Switzerland or France. Instead, check out Bulgaria, Slovenia, and even some parts of Poland. >> Best places to spend a 3-week holiday.

Activities you want to do and your companion

Speaking of this, it’s important to know if you are planning to do specific trips and remember to be flexible and set your mind that your plans won’t always get according to the way you want them to.

When to book

This is crucial both on depending how much money you can spend, another is if your destination is very popular that it has a limited number of visitors that can visit a day, another one is obviously if it’s a busy season like Christmas or Lunar New Year.

Organised tour or not

This is a hot topic in the travel community, travellers don’t want to join an organised tour because of this and that. But here’s food for thought, do what you want to do and what you are comfortable with but remember that some places can only be reached if you join a tour.

There are many reasons, some are simply to keep things in order but other situations are for the local government to provide jobs, keep the place clean and the visitors safe. As a visitor yourself, your job is to follow the rules.

Personally, I like organised tours, they are convenient and affordable. When I go on a vacation, I plan to join the places I want to see through an organised tour and half through my own exploration. For example, I prefer to walk around capital cities while I definitely like to book a tour if I’m going snorkelling or visiting vineyards.

Your preferred way to get around

Whether it’s flying internationally or domestically for convenience, taking the train for the view, bus for the budget, or renting a car for being in control – getting around should be planned a few days before you move from place A to B.

If you are travelling with a medical condition that hinders your movements, you also need to consider that and plan accordingly. The best way to get information about going around in a new place is to speak to your hotel receptionist, they have the best knowledge and are willing to share them without you having to pay for that information.


What type of accommodation

If you don’t have lots of experience travelling, there are many types of places you can stay. Apart from regular hotels, there are hostels for those who are on a budget. A guest house is a good place to stay if you want to have a local experience, often, they are locally owned and the owners live around the same compound/building, and AirBnBs are there too.

If you are disabled, you always have to check that there are ramps or a lift in your accommodations to ease your travel experience. If you are travelling with your pet, make sure the place accommodates pets. Bottom line is, that you need to remember to choose the most comfortable and suitable place to stay for you and your needs.

Slow travel or busy itinerary

I’m a slow traveller but I don’t blame those who like to have a busy itinerary. I understand that not everyone has the luxury to travel with an open itinerary. When you slow travel, it’s definitely cheaper and gives you the time to soak up and learn an extra thing or two about the place you are visiting.

A busy trip means you can see as many places as you want to, it can be expensive but at the end of the day, you did what makes you feel that you didn’t waste a second on this trip.


Free up your time

First things first, make sure you schedule time out of your day to work on writing an itinerary. Trying to make one in the middle of a busy day will only slow down this process and most likely will confuse you resulting in missing many things.

Just provide 1-2 hours without interruption. If you work full-time, the weekends at night are the best time to do it. If you have kids, ask your partner to be in charge of them or wait until they are tucked in bed.

Pen or paper / Digital notepad

You will need somewhere to write this down. It can be a paper or phone or your computer. Personally, I would use a pen and paper plus my laptop or my phone combo since you will need a device to look things up online.

I highly recommend using a spreadsheet though, it’s easier and more convenient to share with your travel companions so they have a copy or they can edit it if they have any questions.


Consider your travel buddies

If you are not travelling alone, make sure to ask your travel companions in advance. In this way, it will be easier for you to decide on many things without going back and forth with your friends. If you ask them the moment you’re writing the itinerary, it can take longer.

If your travel partner wants to get involved, set up a date to do this together or tell them to be available during the time you’re writing an itinerary; they should be easy to reach out to and will reply fast.

If you’re travelling with your kids, make sure to ask them and write down things that they want to do as well not just things you think they want to do. In this way, everyone is happy.

Calendar and a map

You will need a calendar that will help you make mistakes when booking hotels, buses, flights, and tours. I’ve made this mistake too many times.

You also need a map, the best is with your phone. This helps you visualise how far the destinations are from each other which helps you avoid cramping your itinerary.


Here’s a step-by-step guide on how to write an itinerary. I will include an itinerary sample for a cross-continent flight.

Write down the dates on one side and places to see on the other

On your paper or digital paper, create five (5) columns. Fill out the columns with the following texts: date, activities, where to stay, how to get there, and notes.

At this time, I assume that you already booked your flights. If so, mark your fly-out dates and flight back home. Add notes that you think can be helpful like journey time, what time you will land, etc.

Mark the date when you will land at the destination if the date is different from your departure. If it’s a long flight and includes a big time zone change, I recommend you use your first day as a relaxing day to catch up on some sleep. shower, and walk around the city.

What you want to do

Now, you want to go online and check the things you can do at your destination. Try searching for “top things to do in XYZ” or “what to see in XYZ”. You can also be more specific like “hiking in XYZ” or “best beaches in XYZ” or “kid-friendly activities in XYZ”.

Start listing the activities and places you are interested to do under notes. For example, “hike the ABC trail”, “join a cruise for 3 days in ABC”, “food tour in ABC”.

How many days in each place and what to do

The next step is to write next to the activities how many days do you want to do it or the number of days a specific activity will take.

For example, “hiking in ABC trail can be done between 1-3 days”, meaning you can do this hike for just a day or even longer.

One thing to remember, there are organised tours out there that covers multiple activities all at once. For example, you want to see Church A, Lake B, and Museum C. Mark these kinds of activities that you know can be done in one day.

How to get from point A to B


In the next column, you can add how you are planning or the options on getting from point A to B. You should add the travel time as well depending on the type of transportation, In this way, you can easily decide which one is the best mode of transportation for you and can even discuss it with your travel companions easily.

For example bus, 8-hour ride ($10), train 12-hour ride ($20), plane 1-hour flight ($35 plus must be at the airport 1-2 hours before the flight). You can also mark here if the only way to get there is through an organised tour, make a note of the cost per person.

Do this until you finish all the dates and are satisfied with all the activities you’ve chosen.

Here are the tools I recommend you use to check if there are tours you can book, how long it will take, how to get there, and the costs.

  • Get Your Guide: tours and private transportations (worldwide coverage)
  • Klook: tours and private transportations (best if you are going to Southeast and East Asia)
  • Viator: tours and private transportations (best for Europe, North America, and the Middle East – but this have a worldwide coverage)
  • 12go.Asia – for transportation around Southeast Asia and some East Asian countries
  • Flixbus – bus transport around Europe or North America
  • Skyscanner and Momondo – are awesome sites for flights, accommodation, and car rental
  •, Agoda, Hotels Combined, and Hostel World – for accommodations (worldwide)
  • Rental Cars or Auto Europe – to get the cheapest and wide options for cars to rent

Where to stay

The next column will be for accommodations. First, mark the cities where you will be spending overnight and how many nights you are planning to stay. You should also note down the date you are planning to leave this city.

For example, ABC city, overnight for 3 nights and 4 days. On day 4, depart ABC city.

Use a coloured marker or background shade (for spreadsheet) which will help you look over your itinerary without reading all the information out there.

This sample below shows your two shades, one is green and the other is blue. The blocks that are marked green meaning you will spend June 18 and 19th in the same city for 1 night and two days.

The blue shade represents your stay in ABC city, which is from June 20-23, making the 23rd as a departing date.

Now, on the “Where to stay” column, add the name of the hotel or accommodation you want to stay in (don’t book it yet but check the date availability)


Once you finish your first draft, if you still have the time and energy, go over it making sure that there are no overlaps. Not noticing any date or activity overlap is an easy mistake. It’s important to check the dates and that you have enough time to travel between cities.

This is why I personally make the first 24 hours after I arrive in the new city a “lazy day” or an easy day to spend walking in the city, reading information about restaurants to try, etc to give me wriggle room for mistakes and of course and simply just have a light day and not stress myself too much.

It’s also a good idea to take a break from this, either a quick break or get back to it after a day. It’s better to have some fresh eyes when reviewing your itinerary. I can only imagine you’ll be tired of looking at your spreadsheet and browsing the internet for hours.

Booking up

Now that you have reviewed your first draft and I assume you have made some edits or have reached your final draft and have spoken to your travel buddies and got thumbs up with the plan – it’s time to book things up.

Remember, you don’t need to book everything now as I mentioned before. But I recommend you book the flights as soon as you can or as soon as you find the best deals. Flight tickets are the most unpredictable part of the planning. For international flights, they change very fast compared to domestic flights.

However, if you are going during high or peak season (in the destination), it’s best to book your hotels and tours in advance as well. You don’t want to end up settling down in a hotel with no working AC or a hotel with such bad reviews.

Tours get full-booked too, make sure to look up the availability of the date you want to go. Below are the travel sites and tours I always go to when booking any travel arrangements. They have a wide-range, are more affordable, and are very easy to use:


Writing an itinerary can be stressful the first time but once you get a grip of it, it’s an easy flow and actually fun. An itinerary doesn’t have to be a complete one, you only need to give yourself a good overview of how a trip will go through.

I hope this guide helps you with how to write an itinerary for a 3-week trip. If you have questions or have more tips to add to this article, let us know in the comment section below.


Creating a travel itinerary? Start by researching your destination, prioritizing must-see attractions, and balancing activities with relaxation. Book accommodations and transportation in advance, and leave some flexibility for spontaneous adventures. Always keep travel documents handy. via @threeweektraveller