Planning holidays ahead of time has a clear advantage, since you get better prices, more options and less stress. And when the calendar lines up public holidays on strategic days, careful use of just a few days off can turn into a much longer break than you’d expect.
In 2027, there are several chances to do exactly that, and some of them are particularly generous. We went through the national holiday calendar for 2027 and worked out the dates that are genuinely worth booking time off around. Spoiler, the start and end of the year are where things get interesting.
The best 2027 dates for travelling on the fewest holiday days
january kicks the year off in style
The year starts with an easy win. New Year’s Day falls on a Friday, which automatically creates a three day long weekend without using a single holiday day. Book Monday 4 January off too and you get four days in a row right at the start of the year, ideal for an unhurried New Year getaway.
February brings carnival, for those who get the day
Carnival falls on Tuesday 9 February. It isn’t a mandatory public holiday, so it depends on your employer, but if you get the day off, the opportunity is a good one. Book Monday 8 February as well and you get four days off in a row starting from Saturday. This is one of the most popular travel windows of the year, so if it works for you, book early, as prices climb quickly the closer the date gets.
March offers a generous window at easter
Good Friday falls on 26 March, a national holiday. With Easter Sunday on 28 March, you’re guaranteed a long weekend. Book Monday 29 March as well and you get four days in a row. For a more generous break, taking the previous week off, from 22 to 25 March, gives you more than ten days in a row for just five days of holiday.
May and june bring bridges worth taking
Corpus Christi on 27 May and Portugal Day on 10 June both fall on a Thursday. Each one creates a natural bridge if you book the Friday off too, since a single day of holiday buys you four days of rest in both cases. These are two nearby opportunities that, combined with the weekends either side, allow for two short spring breaks without much dent in your holiday balance.
November has the best positioned holiday of the year
All Saints’ Day on 1 November falls on a Monday in 2027, about as favourably placed as a public holiday can be. Without using a single day of holiday, you get a guaranteed three day weekend. Stretch it back to the previous Friday, 29 October, and you get five days in a row for just one day of holiday. It’s the best opportunity of the second half of the year.
december’s double bridge is worth planning for
December has two midweek holidays that, taken together, create an interesting opportunity. Restoration of Independence Day on 1 December and Immaculate Conception on 8 December both fall on a Wednesday. On their own, each allows a small break without much impact on your holiday balance. But book the days of 2, 3, 6 and 7 December, four days of holiday, and you get eleven days in a row, running from 29 November to 9 December. It’s one of the best opportunities of the year for anyone after a longer break without waiting for Christmas.
The 2027 holidays that fall flat
It’s not all good news, since several holidays fall on weekends in 2027. 25 April lands on a Sunday, 1 May on a Saturday, 15 August on a Sunday and Christmas Day on a Saturday, four public holidays that get swallowed up by the weekend with no extra benefit. These are the dates not worth planning time off around, since they don’t create any additional advantage.
In short, the three windows that pay off most in 2027 are Easter in March, the 1 November holiday and the combination of the two December holidays. Anyone who plans ahead, and especially anyone who books travel early, will get these breaks at noticeably better prices than those who leave it until the last minute.
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