The Leave Year 2027: Plan Your Annual Leave Around a Life You Actually Want

I love travelling, but the point of our annual leave plan is not to cram as many trips as possible into twelve months.

It is the opposite.

At the start of the year, we decide where the natural pauses should be. We normally keep at least three consecutive weeks for our summer holiday. We take a week around Carnival — we are from Brabant, and Carnival is part of our year. We usually want another week in autumn, and I like having roughly two weeks away from work around Christmas and New Year.

Those are our anchors.

Someone else’s anchors may be completely different: school holidays, a festival you attend every year, visiting family abroad, a birthday, a walking week, or simply a quiet week at home every spring.

The useful question is not, Where should I go on holiday?

It is: What do I want my year to feel like, and where will I need room to stop?

Before playing with dates, check what you actually have available.

In the UK, almost all workers are legally entitled to 5.6 weeks of paid holiday a year. For someone working five days a week, that is normally at least 28 days. An employer can count bank holidays within that statutory entitlement, and employers can also offer additional leave. See GOV.UK: holiday entitlement.

So do not start with somebody else’s viral “turn 25 days into 50” calculation.

Start with your contract.

Write down:

Only the number left after that is your planning budget.

This is the part I would not skip.

Before looking for clever bank-holiday combinations, Bas and I put our fixed holiday weeks into our shared iPhone calendar. We request those core weeks from our employers early in the year too, rather than building an imaginary calendar and discovering later that the dates are unavailable.

Our anchors usually include a Carnival week, at least three weeks in summer, an autumn break and time around Christmas.

Yours do not need to look anything like ours.

Think about the periods you would genuinely miss if work swallowed them. Those deserve first refusal on your annual leave.

Now zoom out.

If one break ends in March and the next does not begin until August, the calendar may be technically efficient but it probably will not feel very generous in June.

We try to distribute our weeks so there is something to look forward to every so often rather than spending a huge proportion of our allowance in one burst.

I do not use a strict rule such as “a holiday every six weeks”. Life and work are rarely that tidy. I simply look for stretches that feel too long and ask whether one of our movable weeks would be better there.

This is where planning the year on one page helps enormously. If you are also choosing where to spend the time, Building Your Seasonal Travel Calendar is the companion piece.

For readers working in England and Wales, the official 2027 bank holidays are listed below, as published on GOV.UK: UK bank holidays.

Scotland and Northern Ireland have different public-holiday calendars, so use the dates that apply where you work.

And remember: a bank holiday is not automatically an extra paid day off. Your employment contract determines how it interacts with your annual leave.

If you work a standard Monday-to-Friday pattern and the England and Wales bank holidays above are days you would already have off, 2027 offers several useful bridges.

For us, Christmas is usually a larger protected block anyway, so I would look at the whole festive period rather than automatically chasing the most efficient three-day combination.

There is a danger in annual-leave planning becoming another productivity contest.

I do like getting a long break for relatively few leave days. We deliberately look at clusters such as Easter and the May bank holidays for exactly that reason.

But the most mathematically efficient plan is not necessarily the best year.

Perhaps the cheap flights are on a different week. Perhaps your favourite destination is beautiful in October. Perhaps you desperately want three uninterrupted summer weeks and do not care that they sit nowhere near a bank holiday.

Use the bank holidays as leverage, not as instructions.

This is the part of our system I value more every year.

We never allocate all of our leave at the beginning of January.

Once our main weeks are requested and sitting in our shared calendar, we deliberately keep days available. That means that if something lovely appears — a long weekend away, an invitation, a trip we had not considered — we can say yes without dismantling the rest of the year.

It also means there is some breathing room if life simply requires a day.

You do not need a large reserve. The number should fit your entitlement and circumstances.

The principle is simply this:

A fully allocated calendar may be efficient, but an intentionally unfinished one can feel much more free.

If you want to plan your own 2027 leave year, this is the order I would use:

That is it.

No need to optimise all 365 days.

The goal is not to build the cleverest calendar. It is to look at the year ahead and see regular pockets of time that are yours.

I made the printable I wanted beside me while doing this: a year-at-a-glance page, space to calculate your real leave allowance, your personal anchors, the England and Wales bank-holiday opportunities and — importantly — a place to decide how many days you are not going to allocate yet.

Print it, make a coffee, open the calendar you share with the people who matter, and plan the year before it fills itself.

The same planning mood runs through The January Reset, which is how I settle back into the house and the diary once Christmas is over.