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Book a demoWant to make annual leave go further in 2027? With a little forward planning, your team could turn 28 days of annual leave into nine weeks of well-earned time off.
At Charlie, we’re all for our team taking time off. We know how stressful work can be, and we encourage our team to use their 25 days of annual leave regularly, and to book at least some time off every quarter.
Of course, that means a lot of our team members tend to make the most out of the days off. And whether they’re dreaming of a fortnight in the sun, a weekend away with friends or just some uninterrupted time to recharge at home, we know it’s important.
And by strategically combining annual leave with weekends and UK bank holidays, holiday allowance can turn into more than two months away from work.
That said, making the most of annual leave isn't just about squeezing in as many consecutive days off as possible so your team is off. It's also about giving people enough time to rest throughout the year, without leaving yourself short when you need a break. And from an employer’s perspective, it’s ensuring you have enough staff to cover the work that needs doing.
So, let's look at how to make annual leave go further in 2027 – advice for employees and employers.
The trick is simple. By booking annual leave on the working days that sit between weekends and bank holidays, you can maximise your time off without having to use additional days or take unpaid leave.
For example, if a bank holiday falls on a Monday, taking the following Tuesday to Friday off gives you nine consecutive days away from work, using just four days of annual leave.
Doing this a few times throughout the year can then stretch your standard holiday allowance much further than you might expect.
It’s worth noting, though, that not every employee can ‘maximise’ their annual leave allowance.
For a full-time employee working five days a week, the statutory minimum annual leave entitlement in the UK is 28 days, including bank holidays. Some employers offer bank holidays on top of this allowance, while others have more generous holiday policies.
That distinction matters when you're planning your time off, so check your company's policy before booking anything.
If you’re ready to get your 2027 holidays booked in early, here are six opportunities to turn your annual leave into longer breaks.
The examples below are based on the bank holidays in England and Wales and assume a Monday-to-Friday working pattern, with bank holidays taken as non-working days in addition to the annual leave dates listed.
Book off: Monday 4th January to Friday 8th January
Annual leave used: 5 days
Consecutive days off: 10 days, from Friday 1st January to Sunday 10th January
New Year’s Day falls on a Friday in 2027, making it the perfect starting point for a longer break. By taking the first full working week of January off, you can enjoy ten consecutive days away from work.
It’s the perfect opportunity to slowly ease yourself into the new year, catch up with friends and family, or get away before the usual January routine kicks in. It's also a useful reminder that you don’t have to wait until summer to take a proper holiday.
Chief of Staff advice 💡
Depending on the industry you’re in, January can be one of your busiest months. At Charlie, everyone who puts HR software on the back burner comes back in the new year ready to subscribe. So B2B companies should think ahead before allowing team members to take too many consecutive days off in January.
Book off: Monday 22nd March to Thursday 25th March, and Tuesday 30th March to Friday 2nd April
Annual leave used: 8 days
Consecutive days off: 16 days, from Saturday 20th March to Sunday 4th April
Easter is one of the best opportunities to maximise your annual leave in 2027. Good Friday falls on 26th March, followed by Easter Monday on 29th March. By booking the four working days before Easter and the four working days afterwards, you can create a 16-day break using just eight days of annual leave.
That's more than two weeks away from your inbox, meetings and everyday responsibilities, making this one of the most generous breaks available in the 2027 calendar.
Chief of Staff advice 💡
A lot of team members will want to be off during this period – this is mainly because the combination of bank holidays allows for a lot of holiday maxxing. You should let your team rest, but the smart move might be to put some restrictions, such as at least one or two people in the team needs to be present. Putting rules in place and alternating time off year on year might avoid team conflict arising.
Book off: Tuesday 4th May to Friday 7th May
Annual leave used: 4 days
Consecutive days off: 9 days, from Saturday 1st May to Sunday 9th May
The early May bank holiday falls on Monday 3rd May next year, giving you another easy opportunity to extend a long weekend. Take the four working days afterwards, and you’ll have nine consecutive days off, using just four days of annual leave.
Chief of Staff advice 💡
Some of your team members might have not taken any holiday by this time of the year. This raises some red flags. Push people who have not yet taken any holiday to take time off now, whether that’s with maxing out their holiday or just simply going on a long trip to avoid a pile-up of leftover leave in Q4.
Book off: Tuesday 1st June to Friday 4th June
Annual leave used: 4 days
Consecutive days off: 9 days, from Saturday 29th May to Sunday 6th June
The spring bank holiday falls on Monday 31st May in 2027, giving you another opportunity to enjoy a nine-day break without using up too much of your allowance.
If you don’t fancy taking a full week away, this is also a good opportunity to enjoy a few days at home, visit family or plan a shorter trip without having to travel during the busiest part of the summer holiday season.
Book off: Tuesday 31st August to Friday 3rd September
Annual leave used: 4 days
Consecutive days off: 9 days, from Saturday 28th August to Sunday 5th September
The summer bank holiday falls on Monday 30th August, so taking the following four working days off gives you another nine-day break. If you'd rather avoid travelling during the busiest weeks of the school summer holidays, this could be a good opportunity to enjoy a late-summer getaway.
One thing to flag: September, October and November don't have any bank holidays in England and Wales. So, if you used up most of your allowance during the first part of the year, you could find yourself with a long stretch before your next break.
Chief of Staff advice 💡
Think about what’s happening for your business in September. Is it quiet, busy? Make decisions on approving holidays based on business needs as this might be a crucial time for growth.
Book off: Wednesday 29th December to Friday 31st December
Annual leave used: 3 days
Consecutive days off: 10 days, from Saturday 25th December 2027 to Monday 3rd January 2028
In 2027, Christmas Day falls on a Saturday and Boxing Day falls on a Sunday. In England and Wales, the substitute bank holidays fall on Monday 27th and Tuesday 28th December. So, by taking Wednesday 29th through to Friday 31st December off, you can enjoy ten consecutive days away from work, running through to the substitute New Year’s Day bank holiday on Monday 3rd January 2028.
Chief of Staff advice 💡
December is famously a time to slowdown. At Charlie, we used to take two full weeks off during Christmas, but we recently changed this to ensure coverage up until everyone switches off for Christmas. Consider what you’re offering at this time of the year: how to best be prepared for what’s happening in the new year? Will you offer time off on top of the regular allowance or will you opt to give some days off and encourage people to take days off? If everyone is off during this period, we encourage the team to take days off too.
Let’s add it all up.
By combining your 28 days of annual leave with weekends and bank holidays, you could in theory create 63 days off across 2027 and early 2028.
That’s more than two months away from work, without taking a single day of additional leave.
Not necessarily.
While it might be tempting to book every day strategically and squeeze as much time off as possible out of your allowance, there are a few things to consider before putting in your requests.
One of the downsides of maximising your annual leave is that you can end up using most of your allowance early in the year.
As the examples above show, there are several opportunities to create longer breaks between January and early September. But with no bank holidays in England and Wales during September, October or November, you could be left with a long stretch of work before your next planned holiday.
And taking regular breaks matters. Annual leave gives you the necessary time to rest and step away from work before stress starts to build.
Rather than using all your allowance on a few big trips, think about what will actually help you feel rested throughout the year. That might mean a longer summer holiday, a few extended weekends and some individual days off in between.
Life doesn’t always follow the calendar.
You might want a day off for a birthday, a family commitment, a last-minute trip or simply because you need a little breathing room.
Keeping a few days of annual leave unbooked gives you that flexibility when plans inevitably change.
Not all employers calculate annual leave in the same way.
Some include bank holidays within the standard 28-day allowance, while others offer them on top. Some companies also offer additional leave based on length of service, or have different arrangements for part-time employees and people who work shifts.
Before booking your holidays, make sure you understand how much leave you’re entitled to and which bank holidays count towards your allowance.
If you’re unsure, our free holiday entitlement calculator can help you work out your allowance, including pro-rata entitlement for part-time employees.
Making the most of annual leave isn’t just an employee responsibility. Employers have an important role to play in creating an environment where people feel comfortable taking their full allowance and switching off properly when they're away.
That starts with making annual leave policies clear, encouraging people to plan ahead and ensuring nobody feels guilty about taking time off.
It's also important to balance individual holiday requests with the needs of the wider team. If too many people are away at once, it can put pressure on those who remain at work, making it harder for everyone to enjoy their time off.
This is where having a clear view of who’s taking leave and when can make a real difference.
With the right time off management software, businesses can manage holiday requests, track allowances and see upcoming absences in one place. You can see when absences overlap and arrange cover before approving requests.
After all, annual leave isn’t simply a benefit to be used up before the end of the year. It’s an essential part of helping people rest, recover and return to work feeling refreshed.
Our guide to managing annual leave in a small business shares how we’ve handled these challenges at CharlieHR.
Planning your annual leave ahead of time can make a big difference to how much you get out of it. By combining bank holidays with a few carefully chosen days off, you could turn a standard allowance into several extended breaks throughout 2027.
But don’t get so caught up in maximising the numbers that you forget what annual leave is actually for.
Take the time to plan the trips you’ve been dreaming about, book the odd long weekend and leave yourself enough flexibility for the unexpected. Most importantly, make sure you’re taking regular breaks rather than saving all your time off for one big holiday.
And if you’re responsible for managing a team, make it easy for everyone to do the same.
Ready to make annual leave easier to manage? Find out how CharlieHR helps businesses manage time off.
