By the end of next month, Mr Jevons Ang, 33, will have vacationed in India, South Korea, Japan, Taiwan, Hong Kong, Thailand and Malaysia, even visiting some places twice this year.
The bachelor, who works in hotel business development, travels for leisure an average of six times a year, spending $10,000 to $15,000, about 25 to 30 per cent of his annual income, to fund his trips.
To keep costs down, he finds deals on accommodation using websites such as Expedia and Agoda, and avoids travelling during peak periods. Without a car, mortgage or having to pay rent, he gladly spends on travel, his biggest expense.
"I would spend more if I had to because I love it. But I'm a very strategic shopper," says Mr Ang, who devotes up to a month to research, plan and save for long trips.
He is not the only one shopping for experiences abroad. A survey of Singaporean travellers taken at the Natas Holidays 2014 travel fair in August revealed that 17.1 per cent of travellers make four or more overseas trips a year.
According to frequent travellers, their travel is often split between one or two trips to long-haul destinations such as the United States and Europe, and shorter regional excursions to places such as Phuket, Bali and Hong Kong.
Though Credit Counselling Singapore has said that over-spending on travel and cars is one of the most common reasons people fall into debt, frequent travellers say taking multiple trips a year is affordable if done wisely.
Some, such as Ms Winnie Goh, 40, plan their trips based on airfare sales and deals. Ms Goh, her husband and two young daughters aged six and seven, spent five days in Hong Kong in September, capitalising on cheap airfare. The family paid $1,200, including taxes, for their round-trip tickets on Singapore Airlines.
They will spend about the same amount to fly budget airline Jetstar to Phuket for a family trip next month. Saving on airfare allows them to spend more on the accommodation necessary for a family of four, says Ms Goh.
The family travels overseas at least four times a year, and has two staycations, spending 25 to 30 per cent of their annual income on travel - the same amount earmarked for mortgage.
"We budget for travel every year because the kids learn so much. It is also important to take them to places we love, such as Australia where I studied.
"Travel is about bonding and sharing experiences. It's a big part of our life," says the personal assistant, whose husband is a technician at Exxon Mobil.
Some frequent travellers make their trips more affordable by saving on accommodation. Ms Michelle Williams, 24, a hotel service manager, takes an average of six trips a year and stays at hotels where she receives a staff rate, or bunks with friends.
Administrative assistant Low Qiuying, 26, travels about four times a year and tracks accommodation deals on websites such as Bookings.com or stays in backpacker hotels, where travellers can find beds for $5 to $50 a night.
Cutting down on transport and lodging are key considerations. A MasterCard Consumer Purchasing Priorities Survey of more than 400 people taken in July showed that transport takes up the largest portion of the Singaporean's holiday budget at 36 per cent, followed by 22 per cent for accommodation.
Sticking to a daily budget is another way to control one's spending.
For her 18-day trip to the United States last April, Ms Williams budgeted $100 a day for food, drink and transport.
"I give myself a bigger budget than I'd like to spend, just to be safe, but I usually spend less," she says. Purchases are made with cash or a debit card; she does not have a credit card.
Credit cards, however, are the preferred payment mode, according to travel agents.