A family holiday is often an opportunity to step away from everyday routines and spend time together. However, when grandparents, parents and younger family members travel as a group, planning a trip that everyone can enjoy can be a different experience from travelling with people of a similar age.
Each generation brings its own perspective to a holiday. Grandparents may have different travel experiences and expectations from parents, while younger travellers may have their own ideas about what makes a destination interesting. Bringing these different perspectives together can make a family trip a richer experience, but it also means that the needs and preferences of everyone deserve consideration.
Multi-generational travel is not simply about choosing a destination that appeals to the whole family. It is also about understanding what each generation hopes to get out of the journey and finding common ground along the way. The experience can offer family members a chance to discover new places together, appreciate one another’s perspectives and enjoy time away from their usual responsibilities.
For families in Singapore, where work, school and other commitments can make it difficult to bring everyone together, a holiday can be a meaningful occasion for different generations to reconnect.
To explore this topic further, we speak with Anthony Lu, Regional Director for South East Asia and Greater China at Booking.com, about multi-generational travel and the considerations involved in bringing different generations together on one holiday.
Interview with Anthony Lu, Regional Director for South East Asia and Greater China at Booking.com
1. Booking.com’s Travel Happiness Index found that 59% of Singaporeans identify family trips as the most enjoyable. What do you think makes travelling together so rewarding for Singaporean families, and what does this tell us about the role of travel in bringing families closer?
Anthony Lu: “For many Singaporean families, balancing work, school and everyday commitments means quality time together can be hard to come by. Travelling offers a chance to step away from these routines, share new experiences and be fully present with one another.
This desire for connection is reflected in the research, with 40% of travellers citing spending quality time with family, friends or loved ones as a motivation to travel, while 33% identify travelling with family and loved ones as the most important factor in making a trip memorable, enjoyable and stress-free. This is especially rewarding when three generations travel together. Shared experiences help different generations understand one another better, grow closer and create lasting memories that endure long after the trip itself.”
2. When grandparents, parents and Gen Z travellers have different interests and expectations, how can families involve everyone in the planning process and agree on an itinerary that feels fair to all generations?
Anthony Lu: “A good starting point is to bring the family together and have everyone suggest an experience they’d like to include in the itinerary, while being mindful of each person’s needs and preferences. This helps ensure everyone has a say and turns planning into a shared experience.
Our Travel Happiness Index shows 60% of APAC travellers enjoy the planning process itself, making it a great opportunity for families to bond and build excitement even before the trip begins.
Having the right tools can also make it easier to accommodate everyone’s preferences when it comes to building an itinerary, from cultural activities to more adventurous outings. Booking.com highlights wheelchair-accessible options and skip-the-line tickets available for selected experiences.”
3. What are the most important factors families should consider when choosing a holiday destination and accommodation for three generations, particularly in terms of accessibility, comfort, safety and convenience?
Anthony Lu: “In my experience, the families who travel most smoothly across generations tend to get the practical foundations right before anything else. Accessibility and convenience should come first, from transport connectivity to proximity to essential amenities and how easily family members can get around the destination.
Safety is equally important. Our Travel Happiness Index highlights extreme weather (35%) and health and hygiene risks (34%) as key concerns among APAC travellers, so it’s worth checking seasonal weather conditions, access to medical facilities and any specific health requirements before deciding where to go.
Accommodation can also make a big difference. Families can use Booking.com’s filters to find family-friendly properties with suitable room and property accessibility features like lifts or step-free access and suitable bathroom facilities. Property Q&A and AI-powered Review Summaries also make it easier to understand whether a stay meets everyone’s needs without having to go through numerous reviews.”
4. Travelling with several generations can bring different budgets, dietary requirements and energy levels into the picture. What practical steps can families take to manage these considerations before departure and reduce potential sources of stress during the trip?
Anthony Lu: “For budgets, families should agree on a comfortable spending range and how shared expenses like activities and meals will be managed before making bookings. Our research found that 67% of APAC travellers plan to choose travel dates or destinations based on deals or lower prices. Being flexible with dates and comparing accommodation options can help secure better value without compromising on the experience.
For dietary needs, 17% of APAC travellers cite the availability of food options catering to their dietary requirements as a concern when considering a trip. Researching suitable restaurants in advance or using Booking.com’s accommodation filters to find properties with kitchen facilities can help cater to different preferences and avoid last-minute stress.
It’s also important to plan activities around everyone’s energy levels, allowing time to rest and avoiding excessive walking.”
5. How can families strike a balance between spending quality time together and giving each generation the freedom to pursue its own interests, without making anyone feel left out?
Anthony Lu: “Quality time together doesn’t mean having to do everything together. With three generations travelling, it’s important to strike a balance between shared experiences and personal interests.
What matters more is being intentional about the time everyone does spend together. I’d recommend planning a few activities everyone can enjoy, such as a family meal or sightseeing outing, while leaving room for individuals to explore or rest at their own pace. The key is to discuss preferences openly rather than make assumptions about what different generations might enjoy, so no one feels left out.
Coming together at the end of the day gives everyone the opportunity to share what they’ve discovered, and those conversations can become part of the experience itself.”
6. Beyond sightseeing and visiting attractions, what kinds of travel experiences can help grandparents, parents and younger family members learn from one another, share family traditions and create lasting memories?
Anthony Lu: “Food is a great way to bring generations together, particularly in Asia, where it is deeply connected to family traditions, culture and identity. Visiting a local market or joining a cooking class can bring these stories to life, giving grandparents and parents a chance to share their memories while younger family members discover something new.
With 73% of APAC travellers open to including local food, restaurants or unique experiences in their next trip, there’s a clear opportunity to make cultural discovery part of family bonding. Experiences like traditional craft workshops or heritage walks can also help create shared memories while keeping family traditions alive.”
7. Drawing on Booking.com’s Travel Happiness Index and your regional insights across Southeast Asia and Greater China, what are the key travel trends and insights families should pay attention to, and how can these help Singaporean families plan more meaningful and enjoyable multi-generational holidays?
Anthony Lu: “We’re seeing travellers become more thoughtful about what makes a holiday worthwhile. Rather than trying to fit in as many attractions as possible, there’s greater appreciation for the moments spent together. This is reflected in the 28% of APAC travellers who say quality time and genuine connections with their travel companions bring them the most joy.
Another important trend is the growing role of technology. With 84% of APAC travellers saying digital tools make planning and booking easier, families can make use of features such as Booking.com’s AI Trip Planner to explore destinations and accommodation options that suit different generations.
We’re also seeing travellers take a more flexible approach, with nine in 10 APAC travellers choosing to adjust their plans rather than cancel when disruptions arise. For larger family groups, having alternative options and allowing room for changes can make the experience more enjoyable and less stressful for everyone.”
8. With the year-end holiday season approaching, what are your three most important recommendations for Singaporean families planning a multi-generational trip, from the initial planning stage to making the most of their time together?
Anthony Lu: “My first recommendation would be to plan early, particularly when travelling during the busy year-end period. With school holidays and multiple schedules to coordinate, it’s worth agreeing on the travel dates, budget and key arrangements well in advance. This ties into Booking.com’s Connected Trip vision, which brings accommodation, flights, airport transfers and attractions together on one platform, making it easier for families to plan and manage different parts of their journey seamlessly.
Secondly, prioritise comfort over a packed itinerary. Not everyone will have the same energy levels, so build in rest time and keep the first day relatively light. A successful family holiday isn’t measured by how many attractions you visit, but by how much everyone enjoys the experience.
Most importantly, make space for shared experiences. Whether it’s sharing everyone’s favourite moment over dinner, taking family photographs or starting a new travel tradition, it’s often these simple moments that become the most memorable parts of a holiday.”
A Conversation Across Generations
A multi-generational holiday brings together different ages and perspectives in one shared experience. Anthony Lu’s insights offer a closer look at how families approach travelling across generations and the considerations that come with it.
Planning a multi-generational holiday? Visit Booking.com to explore travel options for your next trip.
We also welcome readers to share their favourite destinations for travelling with family. Stay tuned to Our Parenting World (OPW Media) for more travel inspiration, destination highlights, holiday ideas and exciting travel features!
