For Singapore couples, the biggest relationship milestone is no longer the first kiss but the first holiday together, according to a new survey by travel platform Skyscanner and dating app Coffee Meets Bagel (CMB). The survey of 1,000 Gen Z and Millennial Singapore travellers and 380 Singapore CMB daters found that 47% rank a first trip together as their most exciting relationship milestone, ahead of a first kiss (27%) or holding hands (21%). More strikingly, 93% believe the first trip is a critical test of long-term compatibility.

The findings arrive as Singapore enters what the companies call “cuffing season”, the run-up to the year-end holidays, Lunar New Year and Valentine’s Day when singles are more open to new relationships. Nearly half (47%) of singles say they are more open than usual to dating during this period, and 46% are planning a first trip with a partner in the coming year, though close to a third admit to feeling as nervous as they are excited.

“For many Singaporeans, the first trip together has become the defining relationship milestone,” said Cyndi Hui, Skyscanner Travel Trends and Destination Expert. “Through our partnership with Coffee Meets Bagel, we want to help couples navigate this milestone with greater confidence through travel insights and practical planning tips.”

Travel style as a compatibility signal

CMB’s data shows 71.6% of Singapore daters believe a match’s travel personality reflects who they are as a partner, and 56.3% say a match’s travel style has swayed their interest either way. Couples worry most about differences in travel styles (47%) and disagreements during planning (43%), but 90.5% of daters say long-term potential is proven not by a flawless itinerary but by how a couple handles friction.

Amanda Chong, Coffee Meets Bagel’s Dating Trends and Insights Lead, said honest, transparent communication is what makes daters feel ready to travel with someone, noting that everyday planning moments – discussing budgets, adjusting itineraries – are often stronger indicators of long-term compatibility than grand romantic gestures.

Where couples are heading

Tokyo (39%), Seoul (26%) and Taipei (24%) top the list of ideal first-trip destinations, reflecting a preference for nearby, easy-to-plan getaways. Travellers say they would compromise on activities (51%), budget (50%) and trip length (42%) to secure their preferred destination, and 44% prefer destinations new to both partners over familiar ones.

Skyscanner has curated five affordable, underrated alternatives for first-time couple trips: Kota Kinabalu, Da Nang, Yogyakarta, Xiamen and Krabi, each paired with 4- to 5-star hotel options starting from around $43 a night.