Working a 9-5 doesn’t mean you can’t travel lots. Over the years I’ve enjoyed squeezing every last drop out of my annual leave, and by booking a few carefully placed days, you can turn a long weekend into a proper holiday. You’ve just got to know the best dates to book to maximise your holiday allowance!
So I built a UK annual leave planner to do the maths for me, and now you can use it too. Pop in how many days of leave you get, where in the UK you live and which days you normally work. Then It’ll show you all the best dates to book for 2026 and 2027 to stretch your annual leave as much as possible, because who doesn’t love extra time off work? With 25 days of leave in England, you could be looking at 58 days off in total. I don’t know about you, but that sounds much better to me!
If you’re travelling with kids and you’re stuck to booking time off in the expensive school holidays, just tick the school holidays box and it’ll only suggest breaks that usually fall in term holidays. Once you’re happy with your dates, you can even add them straight to your calendar.
Annual leave planner by Roost & Roam © 2026
Now you know when you’re off, the fun part is deciding where to go! If you’ve got a week to play with around Easter or the May bank holidays, Tenerife and Lanzarote are both perfect for almost guaranteed sunshine without a long flight. If you’d rather stay closer to home for a long weekend, have a look at my UK staycation ideas for plenty of inspiration.
Happy planning!