How to Stretch Your Leave to Maximise Travel in the Second Half of 2026

In the blink of an eye, half the year is over. You might already have used some of your annual leave, and are now wondering how you can stretch your remaining leave allowance to the end of the year.

With only three public holidays left in 2026—namely, National Day, Deepavali and Christmas Day, careful planning is needed to wisely use your annual leave to maximise travel in the second half of the year.

Rising fuel prices due to the closure of the Strait of Hormuz have caused airfares to spike, making the need to squeeze more travel days out of a single overseas trip more pressing.

Luckily, with a bit of planning and good travel insurance, you can enjoy several rewarding overseas trips in the second half of 2026, regardless of how many days of annual leave you still have left.

Here are our tips for making your annual leave work harder and maximising travel time in the second half of 2026.

Singapore public holidays in the second half of 2026

The majority of public holidays in Singapore take place in the first half of the year. By contrast, the second half of the year is relatively quiet.

For the purposes of planning overseas trips in the second half of 2026, here are the public holiday dates to take note of:

Take up to three long weekend getaways without having to take leave

Long weekends enable you to enjoy a three-day overseas holiday without having to take leave.

If you have already used up all or most of your annual leave, you can still go on up to three long weekend getaways in the second half of 2026—over National Day in August, Deepavali in November, and Christmas Day in December.

There are many nearby destinations in the Southeast Asian region that lend themselves well to a long weekend. However, as demand for flights tends to be high over long weekends, you should book tickets as early as possible to keep prices affordable.

Our suggestions for a long weekend

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If you’re itching to update your wardrobe, you can’t go wrong with Thai capital Bangkok. Bangkok is a shopper’s paradise for any budget, thanks to luxury malls like Siam Paragon, bargain hunters’ paradises such as Platinum Fashion Mall and Chatuchak Market, and everything in between.

Prefer to spend your long weekend relaxing on the beach? Southeast Asia is replete with beach resorts in idyllic settings. In Bali, check into a swanky beachside resort such as The Legian, Seminyak or Desa Potato Head Bali, and spend your days soaking up the sun and sea, and your evenings sipping cocktails at beach bars like Ku De Ta and Woobar.

If shopping and hanging out at a luxury resort aren’t your cup of tea, don’t worry, there are still many rich cultural experiences that can be enjoyed just a short flight from Singapore. The bustling Old Quarter of Hanoi, Vietnam, the ancient temples of Angkor in Cambodia and the magnificent Borobudur Temple in Indonesia can be easily visited on a long weekend.

Use your annual leave strategically to extend long weekends

If you have annual leave days to spare, you can always peg them onto a long weekend in order to travel for a longer period.

Just one or two extra days can make a big difference, giving you the time and space to explore a travel destination at a more relaxed pace.

Our suggestions for four- or five-day trips

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With four or five days at your disposal, you can comfortably visit Hong Kong for long enough to see some of the city’s main sights, such as Victoria Peak and the Tian Tan Buddha, while still having time to tuck into dim sum and cha chaan teng classics like French toast.

Alternatively, you might prefer to visit Taipei, where you can load up on street snacks at the city’s many night markets while still having the time to marvel at cultural and historic sights like Longshan Temple and the National Palace Museum.

Travel for up to nine days using four days of leave

If you’re able to schedule four days of annual leave right before or after a long weekend, you’ll be able to travel for up to nine days.

For instance, the Monday after National Day (10 August) is a long weekend. By taking leave from Tuesday to Friday (11 to 14 August), you’ll be able to travel for a full nine days from 8 to 16 August.

With a full nine days to travel, you’ll have ample time to venture farther afield and sightsee in greater depth.

Our suggestions for nine-day trips

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Japan is a firm favourite of travellers from Singapore. In nine days, you’ll be able to explore one or more major cities such as Tokyo, Kyoto or Osaka in depth, taking in iconic sights such as Tokyo’s youth district Harajuku, Kyoto’s historic Gion area and the imposing Osaka Castle.

In nine days, you will also have the time to visit the key sights in a huge cultural hub and megacity in China such as Beijing. Your nine days will fly by as you work your way through the long list of world-famous sights in the city, including the Forbidden City, Tiananmen Square, the Summer Palace and the Great Wall of China.

K-pop and K-drama fans will not want to miss the chance to visit South Korea. If you have already visited capital Seoul, you now have the time to venture to other destinations such as Busan, which is not only a bustling city in its own right but also has the advantage of a coastal location with countless scenic spots, such as the stunning Haedong Yonggungsa Temple, which overlooks the sea, and the Oryukdo Skywalk, a scenic trail which hugs the coastline.

Travel for up to 16 days over Christmas and the New Year

If you’ve been assiduously saving up your annual leave, you can finally enjoy a well-deserved break of up to 16 days at the end of the year.

The Christmas Day public holiday falls on a Friday, as does New Year’s Day on the first day of 2027. If you have eight days of annual leave to spare, you can use them on the Monday to Thursday before Christmas Day (21 to 24 December) and the Monday to Thursday before New Year’s Day (28 to 31 December). This will enable you to travel for up to 16 days, from 19 December to 3 January.

With over two weeks to travel, you’ll have the bandwidth to truly immerse yourself in a destination and travel outside of Asia if you wish, taking advantage of wintertime in the Northern Hemisphere to escape Singapore’s heat.

While it goes without saying that you should purchase travel insurance before your trip, if you have multiple upcoming overseas trips, it might be more worthwhile to opt for an annual travel insurance plan that covers you for 12 months.

Our suggestions for trips over Christmas and the New Year

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If you’ve always dreamt of experiencing a White Christmas, Lapland in Finland is the ultimate destination. You can spend the night in a glass igloo at a resort such as the Kakslauttanen Arctic Resort and visit the famous Santa Claus Village in Lapland’s capital, Rovaniemi.

Another festive destination to visit during the holiday season is Strasbourg in France, whose Christmas Market is one of Europe’s biggest and most famous. You’ll be able to sip hot mulled wine while browsing the various stalls for gifts and local delicacies. As you’ll have over two weeks, you can combine this trip with a visit to Paris or other destinations in France, such as Colmar, a town near Strasbourg said to have inspired the visuals in the Studio Ghibli film Howl’s Moving Castle.