How to Travel Several Times a Year with Only 20–30 Days of Annual Leave

“How much annual leave do you actually get?”

That’s one of the questions that naturally comes up when people see how often we travel.

At first glance, it might seem that if someone manages several trips abroad, weekends around their home country, and one longer holiday in the same year, they must either have unlimited time off or simply not have a regular job.

The reality is much more ordinary.

We both work normal jobs. We just try to use our time off as efficiently as possible.

My situation is slightly different because of my job with the police. I get 30 days of annual leave each year, and I can sometimes add extra days off earned through weekend duties, overtime or additional hours worked.

Not everyone has the same options.

Some people get 25 days of annual leave. Others only get 20.

But the basic principle of planning remains very similar.

It’s not only about how many days of annual leave you have.

What matters even more is where you place those days in the calendar.

Before Looking at Flights, We Look at the Calendar

When we start planning another year of travelling, one of the first things we open isn’t Booking.com or a map of the world.

It’s the calendar.

We mainly look for:

• public holidays,
• Easter,
• Christmas,
• long weekends,
• public holidays that fall on a Tuesday or Thursday,
• periods when a few days of annual leave can connect two weekends.

This is where you can save a surprising amount of annual leave.

One strategically placed day off can give you four days of travel.

Four or five days of annual leave can sometimes turn into nine days away.

Suddenly, those 20, 25 or 30 days of annual leave start looking very different.

It’s Not About the Number of Trips. It’s About How Much Annual Leave They Cost

This is probably the most important principle behind the way we plan our travels.

Take a normal weekend:

Saturday + Sunday = 2 days of travel and 0 days of annual leave.

Add Friday:

Friday to Sunday = 3 days of travel for 1 day of annual leave.

If Monday is a public holiday:

Friday to Monday = 4 days of travel for 1 day of annual leave.

And if the calendar works in your favour:

Saturday to the following Sunday = 9 days of travel for 5 days of annual leave.

That’s already enough time for somewhere like Jordan, Armenia, Georgia, part of the Balkans or a proper European road trip.

My Situation Is Slightly Different

Because of my job with the police, I get 30 days of annual leave, so I obviously start from a better position than someone who only gets 20 days.

I also work certain on-call or special duties. If one of these falls on a weekend, depending on the circumstances, I can earn additional time off that I can use later.

On top of that, there can sometimes be:

• overtime,
• additional hours worked,
• time off in lieu.

So in reality, I may have access to more time off during the year than my basic 30 days of annual leave.

I don’t want to pretend that we have exactly the same circumstances as every other employee.

We don’t.

But a large part of our travelling still isn’t possible because of these additional days.

It comes from the way we combine annual leave with weekends and public holidays.

Public Holidays Are Your Best Friend

Every year, I check in advance which days of the week the public holidays fall on.

The most useful ones are obviously those that create a long weekend or fall close to one.

A public holiday on Monday is simple:

3 days off without using a single day of annual leave.

Friday works exactly the same way.

Tuesday and Thursday can be even more interesting.

If a public holiday falls on Tuesday, you only need to take Monday off:

Saturday + Sunday + Monday off + Tuesday public holiday = 4 days off for 1 day of annual leave.

These are exactly the dates we look for when planning our trips.

Easter Is Perfect for a Shorter Trip

Easter is one of the periods we try to make use of.

The public holidays already create additional time off, and by adding just a few days of annual leave, you can create a very useful block of free time.

It’s perfect for something like:

• a European city break,
• the Balkans,
• a road trip,
• a few days in the mountains,
• a shorter trip abroad.

Not every trip needs to cost ten days of annual leave.

Christmas Can Be Even Better

Christmas works in a similar way.

Of course, it depends on which days of the week Christmas falls on in a particular year.

When the calendar works out well, a few days of annual leave can connect Christmas, weekends and New Year.

The result can be a surprisingly long break while using relatively little annual leave.

That’s another reason why planning your year in advance can make such a difference.

The Biggest Trick? Connect Two Weekends

We use this one a lot.

If we leave on Saturday and return the following Sunday, we are away for:

9 days.

But we only need to take:

Monday, Tuesday, Wednesday, Thursday and Friday off.

That means:

5 days of annual leave → 9 days of travel.

And if there happens to be a public holiday during that week, it can become:

4 days of annual leave → 9 days of travel.

That is a huge difference.

What If You Only Have 20 Days of Annual Leave?

Even with 20 days, you can travel surprisingly often.

I just wouldn’t automatically divide them like this:

10 days in summer + 10 days in winter = no annual leave left.

There’s absolutely nothing wrong with doing that if those are exactly the holidays you want.

But if your goal is to take several different trips throughout the year, we think there’s a better way to use those days.

Here’s a simple example.

First Main Trip

5 days of annual leave
→ 9 days away by connecting two weekends

Second Main Trip

5 days of annual leave
→ another 9 days away

Annual leave used so far:

10 days.

You still have another 10 days left.

You could use those for, for example:

• two long weekends costing 1 day each,
• another trip using 4 days of annual leave,
• several individual days placed around public holidays.

Suddenly, 20 days of annual leave can turn into several completely separate trips throughout the year.

What About 25 Days of Annual Leave?

With 25 days, there are even more possibilities.

For example:

5 days – main nine-day trip
5 days – second nine-day trip
5 days – another longer trip
4 days – trip built around a public holiday
3 days – long weekend
3 days – reserve

And we’re still talking about someone with a normal full-time job.

And with 30 Days?

With 30 days of annual leave, it becomes possible to combine one genuinely long journey with several shorter trips.

We like to combine:

one big trip + several medium-length trips + weekends around the Czech Republic.

And those weekends are important.

A trip to the Ore Mountains, the Giant Mountains or somewhere else in the Czech Republic doesn’t automatically require a week of annual leave.

Quite often, we simply leave after work on Friday and return on Sunday evening.

Annual leave used:

0 days.

And we still get two or three days of travelling out of the weekend.

Friday After Work Is Surprisingly Valuable

We’ve become particularly fond of this approach when travelling around the Czech Republic.

There’s no reason to wait until Saturday morning.

If the destination is within a reasonable driving distance, we can leave straight after work on Friday.

We arrive and check in on Friday evening, and on Saturday morning we’re already there and ready to explore.

Suddenly, we have practically the entire weekend at our destination.

When travelling by car, it’s often the easiest way to get as much as possible out of a normal weekend.

Some destinations are perfect for:

3–4 days.

Others need:

5–7 days.

And it’s usually only the more distant or complicated journeys that really make sense for two or three weeks.

By combining trips of different lengths, you can see much more during the year without using all of your annual leave.

We Don’t Really Count Trips Around the Czech Republic as “Using Up Our Holiday”

Of course, we occasionally take a day off for a trip in the Czech Republic.

But most of our trips around the country are built around weekends.

Friday after work.

Saturday.

Sunday.

And on Monday, we’re back at work as usual.

It certainly isn’t a relaxing wellness weekend.

We often walk more in those two days than we do during an entire normal working week.

But it allows us to keep travelling without touching the annual leave we want to save for bigger trips abroad.

We Always Keep Some Annual Leave in Reserve

We wouldn’t recommend planning every single day of your annual leave on January 1st and allocating it all the way through December.

We like to keep some flexibility as well.

Something unexpected can always appear:

• a cheap flight,
• a spontaneous weekend away,
• an interesting event,
• a change of plans,
• or simply the urge to go somewhere.

If all 20, 25 or 30 days have already been allocated six months in advance, you have very little room to react.

That’s why we prefer a combination of:

big trips planned well in advance + a few days deliberately left free.

No Two Years Are the Same

Some years, public holidays fall perfectly.

Other years, the calendar is terrible.

Sometimes we can use additional time off earned through work.

Sometimes we can’t.

That’s why we don’t have one universal system that we copy exactly every year.

At the beginning of the year, we look at the calendar and build our travel plans around it.

It’s Not About Being on Holiday All Year

This is probably worth mentioning too.

We’re not saying that the best way to live is to spend every free hour travelling.

Some people want to spend part of their annual leave at home.

Some need time off for their family.

Others simply want to take a week off, relax and go absolutely nowhere.

And there’s nothing wrong with that.

The point is simply that if travelling several times a year is important to you, you don’t necessarily need unlimited annual leave to do it.

Sometimes, you just need to use the calendar a little more strategically.