Family holidays are precious, and when you bring three (or more) generations together, they can be unforgettable. But planning a trip for kids, teens, parents, and grandparents isn’t without its challenges.
So how do you keep everyone happy, organised, and relaxed? The key lies in smart preparation and the right destination. Here are five tips for planning a smooth and joy-filled multi-generational getaway.
1. Pick a destination that balances adventure and downtime
When you’re catering to different energy levels and interests, versatility is your best friend. Older travellers may value comfort, culture and slower-paced activities, while kids and teens often seek action and independence.
Look for destinations that offer a variety of options within easy reach. Cultural excursions, beach days, nature walks or even guided activities that different age groups can enjoy separately or together. Urban breaks can work if there’s green space nearby, but resorts or locations with nature access often provide more flexibility for families on different rhythms.
2. Prioritise convenience – especially around meals and logistics
One of the biggest friction points on family trips is mealtime logistics. Figuring out where to eat multiple times a day with a big group, especially with fussy eaters or dietary needs, can add unnecessary stress. Add in transport planning, ticket bookings and budgeting, and it’s easy for the vacation to start feeling like work.
That’s why many families opt for all-inclusive resorts that take care of meals, activities and accommodations in one place. For example, Club Med resorts, located across Europe, the Americas, Asia, and now right her in Durbs, offer a practical solution by bundling meals, childcare, sport and entertainment, so parents don’t have to sweat the small stuff. With no bill-splitting and everything handled on-site, it gives everyone more time to actually relax.
3. Mix shared experiences with personal space
Togetherness is the goal… but not too much of it because even the happiest families can hit their limit. Multi-gen trips work best when they balance quality time with opportunities for solo adventures or downtime.
The best way around this is to build your days around one or two shared activities. For example, a morning hike or dinner together, and then give everyone space to explore or relax on their own. Whether it’s grandparents enjoying a spa afternoon, kids making friends in a supervised kids’ club, or couples sneaking off for a beach walk, space to breathe makes the group moments feel more special.
4. Choose accommodations that fit your family’s flow
Hotel rooms might work for quick city trips, but for longer stays, family suites, villas, or adjoining rooms can be a game-changer. Not only does this provide more comfort, but it makes things like naps, night-time routines, and early-morning wakeups easier to manage across generations.
Some hotels offer multi-room configurations and interconnecting rooms designed specifically for families – think separate sleeping areas for kids, private terraces for grown-ups, and shared living areas. Booking early is essential, especially during school holidays when these options sell out fast.
5. Keep it simple and let the experts help
The best multi-gen trips aren’t over-engineered. Avoid trying to pack in too many destinations or tightly scheduled days. Instead, choose one home base and let the experience unfold from there. Consider working with a travel advisor or booking through platforms that offer tailored experiences.
Many resorts, including a number of all-inclusive brands, offer concierge services that help plan age-appropriate activities or off-site excursions. For instance, some properties even have dedicated family coordinators who can help with everything from arranging transportation to organizing a surprise birthday dinner for Grandma.
A multi-generational trip can be the highlight of your family’s year. It’s a rare chance to slow down, connect, and make memories across age groups. With the right planning, the right setting, and a little room for flexibility, it doesn’t have to be a logistical headache. Pick your place carefully, lean on the pros where it counts, and above all, leave space for joy.
