There is an indication of a growing number of Singaporeans travelling overseas recently despite the current global economy downturns which do not seem to hamper their enthusiasm to escape from the small island in Southeast Asia region. This study aims to identify the trend and factors affecting or influencing Singaporeans from travelling. In addition, to identify what strategies can the travel industry adopt to sustain during crisis. Based on the sample size of five hundred (500) respondents, we concluded that (1) there is a trend towards less expenditure, which has seen a decline in the median of total expenditure from $4000 - $4999 spent in 2008 to $3000 - $3999 for 2009. Despite the current crisis, (2) there is a high turnover on travel by Singaporean residents, which has seen an increase from median of trips from 2-3 trips in 2008 to 4-6 trips per person in 2009. (3) Pearson’s correlation test has revealed that there is a strong relationship between preferred mode of purchase, particularly, online travel booking and age group. (4) A similar test was performed between income and next preferred destination. The result revealed a weak relationship that is income level does not determine subjects’ next preferred destination. (5) These trends of travelling can be supported by a recent theory conducted by various researchers in similar field of study. Suggestions for future research could be carried out in areas such as the impact of turnover on travel (travel frequency) in Singapore, the impact on expenditure for married individual travelling with family and single travelling with companion. Also, the relationship between mode of payment and expenditure given the fast spread of swine flu epidemic and coupled with worsen economic crisis were mentioned.