A step by step guide to planning a trip

A guide to planning a trip

I work full time, so I am dead serious about my vacations. According to our local legislation, I am entitled to 28 paid days off and, luckily, I can get them whenever I want: my boss is gold. During the many years of work in this company, I came out with a holiday routine, so if you are looking for any ideas on planning a trip, I am sharing them here.

I will guide you through all the stages of my travel planning: some might apply to your situation, some might not. Please, keep in mind that I mostly travel to Europe, so all experience is in that direction. I guess a Europe travel checklist will be useful 🙂

Let’s start with the most important thing.

Some of the links below may be affiliate links, meaning that I will get a small commission (it won’t cost you anything!) if you click and book accommodation. As you can see, I do not use advertising on this website, so it will help me to keep this blog going.

When to start planning the trip

I am not one of those people who decide to go somewhere on Monday, and on Tuesday they are in a plane flying to their dream destination. Don’t get me wrong, I admire those people and sincerely hope that one day I will join this league. The main reason I don’t do it now is that last-minute trips are usually very expensive, and, being a budget traveler, I simply can’t afford them. And, considering the fact that my boss allows me to take days off whenever I want, I plan my trips long in advance, like 5-6 months. More accommodation options are available and the prices are lower, what is really important because I tend to travel during or close to the high season. Usually, I start planning my trips in winter: firstly, because I do not travel during this period and have time for that, and lots of airlines start offering discounts for the upcoming months.

Choosing the time of the trip

I don’t like when it is cold or hot, so I choose the time of the visit based on my temperature requirements. The Northern European countries like Sweden, Norway, Russia (not exactly Northern European 🙂 ), are better to visit in the summer months, and the Southern European and some Middle Eastern countries like Italy, Spain, Greece, Turkey, are perfect for visits in April-May and September-November. But, again, it depends on the purpose of your trip: if you want to spend your days on the beach, then summer and September are perfect for Italy and Greece, for example.

I went to the south of Spain in the second half of October, and the weather was perfect! Amsterdam was fantastic in the beginning of June, Moscow was amazing at the end of August. Now I am planning my trip to Istanbul for the end of April, and my vacation in Prague for the beginning of June.

Travelling around Russia: Architectural gems of Moscow
Izmailovsky Kremlin in Moscow, Russia

Choosing destination and flights

This one is pretty easy for me: I want to visit every country in the world 🙂 The main thing that I pay attention to is the visa requirements: I mean, at the moment I choose the places where I do not need visas. I am a dual citizen, so I have a long list of countries to choose from. If you decide to visit South American, African and Asian countries, check if you would need vaccines. And don’t forget about safety: some destinations like Europe, are considered to be safer than, say, African countries.

Logically, the closer the destination is, the cheaper the flights are. I use Skyscanner and Kayak to search for flights: these websites are travel aggregators and search engines. I use them to check what flights are available and which airlines fly to my destination, but I never book through them: I always go to the specific airlines website. Kayak is good when you know your dates and destination, while Skyscanner is good for searching for cheap flights.

Pay a special attention to Skyscanner, if you have no idea where to go: this website is gold when it comes to choosing the destination. For example, you choose your departure airport and instead of putting the arrival airport, type Everywhere, and choose Cheapest month for the dates: the system will show you the destinations with the cheapest flights from your location. Another option is to choose the whole month in the date section, and the system will show you the cheapest flights in that specific time frame.

But a much better option is to subscribe to the newsletters of the airlines that fly from your neighbourhood. I get it, if you live in a big country, there are too many companies operating flights, but it is easy in my case: in Moldova we don’t have many of them. Air Moldova is the biggest one, and they offer discounts several times a year.

There are no budget airlines like Ryanair or EasyJet flying from Moldova, we have some flights offered by WizzAir, so in the end it is quite easy to follow all of them.

Looking for means of transportation

I do not mean here the local transport inside a city, I mean the interurban connections. This is important and especially true in my case, because I visit several cities in a country. This means I have to find out how to get from one place to another and the dates when buses/trains run between these places. Usually I start with Google Maps: I select a place from my list, click on Directions button, type in my destination, and let Google show me the options. Then I check these train/bus companies suggestions in Google Search.

Another way – when Google Maps can’t find anything (yes, this happens!) – is to just type in Google how to get to X from Y: almost all the time I find out what I need. Tripadvisor and Lonely Planet forums are very useful as well: there is a high likelihood someone has already asked this question.

Being a control freak, I buy tickets in advance, and it is cheaper. I still remember that the tickets from Rome to Florence we bought right on the day of the departure were almost 20 EUR more expensive than months before when we checked it online (happened in 2013).

Getting from airport to downtown

The first option everybody thinks of when arriving to a new place is taking taxi. After all, you are taken from the airport directly to your destination and you don’t have to worry about anything. It is convenient and expensive. What if you don’t have money for taxi? Then you might be frantically searching Google for alternative ways of getting downtown. Let me tell you of a place where you can do it: you need to browse the website of the specific airport. Many of them have a menu section where they describe in detail all ways to get to the city, starting with taxis and ending with night buses. For example, take a look at the websites of airports in Prague or Moscow to get an idea of what I mean.

Make a rough plan of the trip

When I visit a country, I try to see several cities: sometimes it means that I will have to move to another city, sometimes it is just 1-day trips. Naturally, before booking accommodation, I need to know how much time I will spend in each of these places. To make a rough guess I do a quick research of things to do.

Researching places to see

I do not go very deep into planning at this stage. What I do is typing in Google things to do in X or places to see in X. I open the first 5-6 links and mark the places in Google Maps: usually, they cover almost everything of interest in that specific place and I make a guess on how much time I would need to see them. Usually I add an additional day or two for other not-so-obvious tourist attractions. And this is the point when I buy the air/bus/train tickets: I know how many days I will spend, so I can check what dates have lower prices.

Choosing accommodation

Honestly, I consider booking accommodation the easiest part: usually, there are lots of options. My personal thing is that I always stay in the center of main points of interest. Well, unless it is very expensive. And this is when researching places to see comes very handy: basing on the starred places in the Google Maps I define the area I want to stay in.

I use two websites to search for accommodation: Airbnb and Booking.com. If you have not heard about it, Airbnb is a booking service where home owners rent out their apartments/flats (at least, this was the original idea). Quite often prices for accommodation are cheaper on Airbnb than hotels. I have a big post on Airbnb here.

Booking.com is a hotel and hostel aggregator, and has many options for any city. As I travel on budget, I book beds in hostel rooms from time to time, if single rooms or hotel rooms are too expensive. So here is my sincere advice: if you book a bed in a hostel, make sure that this room has a private bathroom. Trust me, you don’t want to wait for your turn to WC when you really need it. Yes, these rooms are a bit more expensive, but totally worth it!


What is really handy is that both booking.com and Airbnb have maps, so I can easily identify the area I want to stay in based on the starred places in my Google Maps.

These are the only services I have used and use so far. When I travel to several cities in a country, I usually book a mix of hostel/hotel rooms and Airbnbs, but my first point of reference is booking.com. And if I don’t find anything suitable there, I go to Airbnb (click here for a discount on your first booking with AirBnB).

Making a thorough plan of the trip

After I booked everything, I start preparing a more thorough plan of my trip. This means digging deeper into the places to visit, reading posts in Pinterest, marking those place in Google Maps, searching for prices, discounts, free entrance offers and days off (a very important one!). Then I look at the Google Maps with the starred places, and split it according to the days I stay in a place. Let’s take, for example, Seville. As you can see in the map below, I split it into two days basing on the distance between the sights and approximate time I would need.


Limited budget is one of the reasons I start planning my trips so early. Actually, this way allows me to save enough money before my trip. How do I do it? I don’t have any other ways of earning money except my salary. So, if, let’s say, I start planning a trip in January, and want to travel in June, I spend my December salary on air tickets, my next salary goes to pay for the accommodation, and I have another 4 months/salaries to save some money to pay for entrance fees/food when I am in my destination. But that depends on the salary, of course.

A round-up

– decide when you want to go
– choose the destination (country and cities) and decide how many days you would like or are allowed (depends on the number of days off you can get) to spend there
– book flights
– research places to visit and see how many days you would spend in a city
– book accommodation
– buy bus/train tickets

This is pretty much how I plan my trips. Just curious to know how you do it 🙂


How to plan a trip | A guide to planning a trip | Planning a vacation | How to plan a vacation on a budget | How to plan a trip on a budget | Step by step guide to planning a trip

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