(Singapore, 24 August 2026) For Singapore couples, the biggest relationship milestone today isn't the first kiss or saying "I love you" – it's the first holiday together. A new survey* by global travel platform, Skyscanner and dating app, Coffee Meets Bagel (CMB) found that 47% of Singaporeans say travelling together for the first time is the most exciting relationship milestone, ahead of the first kiss (27%) and even the first time they hold hands (21%). More significantly, 9 in 10 (93%) believe that the first trip is a key test of long-term compatibility.

To uncover how couples are navigating their first trip together, Skyscanner and Coffee Meets Bagel embarked on a survey with 1,000 Gen Z and Millennial Singapore travellers and 380 Singapore CMB daters, to understand the common challenges they face when taking their first trips and share destination inspiration and tips to help them travel with greater confidence.

The findings come as Singapore enters "cuffing season" – the period leading up to the year-end festive holidays, Lunar New Year and Valentine's Day when singles are more likely to seek new relationships – where nearly half (47%) of singles say they are more open than usual to dating. Against this backdrop, 46% of singles are planning to take their first trip with a partner or potential partner in the coming year, but nearly 1 in 3 respondents admit they feel just as nervous as they are excited

Cyndi Hui, Skyscanner Travel Trends and Destination Expert, (left) says, “For many Singaporeans, the first trip together has become the defining relationship milestone – 92% agree that travelling together for the first time reveals compatibilities that everyday dating simply can’t. Couples are making decisions together, managing budgets, navigating unfamiliar situations and balancing different preferences all within a short period of time. Our survey reveals that this is especially true during cuffing season, when more people are looking to build meaningful relationships ahead of the festive period. 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.”

CMB's data supports this as 71.6%** of Singapore CMB daters believe a match's travel personality reflects who they are as a partner, and 56.3% say a match's travel style has actually swayed their interest, either positively or negatively.

Butterflies at 30,000 feet: Excitement meets nerves

Despite the excitement, Singapore couples worry most about differences in travel styles (47%), disagreements during planning (43%). 90.5% of Singapore CMB daters say long-term potential is proven not by a flawless itinerary, but by how a couple handles friction — resolving a disagreement maturely, feeling emotionally safe being vulnerable in an unfamiliar place, and balancing togetherness with personal space.

To help couples prepare, Skyscanner and Coffee Meets Bagel identified three key considerations for planning a successful first trip together.

1.       An ideal destination is one that is stress-free and easy to plan

Securing an ideal destination is key for a first couple’s trip, with Singapore travellers agreeing that they would compromise on planned activities (51%), travel budget (50%) and length of trip (42%) to secure that ideal destination. Based on traveller preferences, Asian countries take the cake as the most popular destinations for first trips, showing the preference for nearby, easy to plan destinations.

2.       Couples are more willing to splurge on a dream accommodation

Travellers say that accommodation is the top expense they would prioritise spending on (28%), followed by activities, attractions, food and flights. But when it comes to booking one, affordability still comes up as the top criteria (44%) – most want to find the best rate or deal, even if it means a location that’s smaller or further from the city. This is followed by proximity to sights and dining (40%) and unique lodging experiences such as a dome, tent, or castle (31%). 

When it comes to accommodations, the map tool on Skyscanner's Stays can help you find stays that stretch your dollar further, often just by looking a short distance from the city centre. 

3.       Singapore couples trade cliches for less-explored territories

Singapore travellers also prefer destinations that are new to both partners (44%), rather than places that one or both have visited before, reflecting a desire to discover lesser-known destinations in creating shared memories and explore a new chapter of their relationship together.

That "neither of us has been here" dynamic may matter more than it seems. Feeling emotionally safe enough to be vulnerable in a new environment is Singapore CMB daters' second strongest indicator of long-term relationship potential (25.6%), something a shared first-time destination can naturally foster.

“74.2% of Singapore CMB daters say honest, transparent communication is what makes them feel ready to travel with someone. Before booking flights, think less about judging your partner and more about observing how the two of you work as a team. Travel planning is full of small moments—from discussing budgets to changing itineraries—that reveal whether you can communicate, compromise and navigate challenges together. Those everyday interactions are often much stronger indicators of long-term compatibility than grand romantic gestures," says Amanda Chong, Coffee Meets Bagel’s Dating Trends & Insights Lead.

When planning a trip together, Singapore CMB daters say the strongest green flag for long-term relationship potential is a partner who regularly checks in on their comfort level, making decisions together rather than assuming.

With these three considerations in mind, Skyscanner has curated a list of five affordable, underrated destinations suited for a first trip, with affordable 4- to 5-star hotels: 

 "For couples looking to make their first trip memorable, a few small planning tricks go a long way," says Cyndi Hui. " Our research shows that couples prioritise destinations that are easy to plan and enjoyable for both partners. One of the easiest ways to discover destination inspiration is through Skyscanner's new travel discovery tool, Explore with AI. Simply enter a prompt like “best cheap and underrated destinations for a couple’s first trip” and you’ll receive personalised recommendations, complete with flight prices and useful information to help you plan with confidence.” With the right planning and the right tools, that mix of excitement and nerves can become one of the most telling, and most memorable, chapters in a new relationship.

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