The Multi-Gen Trip, Perfected

Mar 12
7 min read

Updated: Mar 13

How Many Boxes Does Multi-Generational Travel Really Have to Check?

Multi-generational travel is having a moment. And honestly? We’re not surprised.

After six years of planning trips for families travelling with grandparents, parents, teenagers, and toddlers all in one go, we can tell you these are some of the most rewarding trips we arrange. They’re also, without question, some of the most complex.

You’re not just planning a holiday for two people. You’re planning for ten…fifteen… sometimes twenty family members. Different ages. Different energy levels. Different expectations.

But when it works, a multi-generational trip becomes something really special. These are the holidays families talk about for years afterwards.

A little background on why we love these trips

At Sarah Ives Luxury Travel, multi-generational trips are some of our favourite journeys to plan.

Perhaps that’s because Sarah herself comes from a very large family. With thirteen aunts and uncles and four sisters, big family gatherings were never small affairs. So when families come to us and say, “We’re thinking about travelling with the whole family,” we immediately start thinking about the dynamics.

Because planning for multiple generations isn’t just about choosing a beautiful destination. It’s about choosing the right experience for everyone.

Most multi-gen trips start with a celebration

In our experience, these trips are often centered around something like a milestone birthday, a retirement, a big anniversary - or sometimes simply an excuse to gather everyone together for Christmas somewhere special.

Whatever the reason, the goal is usually the same: quality time together. And when families are travelling with toddlers, teenagers, parents and grandparents all at once, the planning needs to be thoughtful.

Mobility is often the first thing we consider.

That dreamy Italian villa might look incredible in photographs, but if it has hundreds of stone steps and a rocky beach, it may not work for grandparents with mobility concerns or toddlers exploring their surroundings. Multi-generational travel works best when the destination suits the group, not just the aesthetic.

Safari: One of the best multi-generational trips

Safari is one of our favourite recommendations for multi-generational travel when the group is the right fit. It works beautifully when children are around eight years old and older, and when grandparents are relatively active.

What we love most about safari for families is how naturally it brings everyone together.

Teenagers who are normally glued to their phones suddenly forget about them completely. They’re watching elephants cross the road, comparing photographs, and arguing about who spotted the lion first.

A few small additions can make the experience even more special. We often recommend investing in cameras for the children so they can document the trip themselves. Bring binoculars, games for downtime between drives, and if possible arrange a family photoshoot at the lodge. Those photos honestly become treasures.

"I would give more than five stars if I could! Our family just completed our second trip planned by Sarah and her team, and I don't think we can travel any other way again. I initially reached out to Sarah to help us with a trip to Morocco for our family of four. They put together an incredible, personal, and FUN vacation that was such a special experience. For our second trip, Sarah planned a two-week adventure to South Africa for our multi-generational family of ten. It was completely tailored to our needs and interests and greatly exceeded everyone's expectations. Everyone from age 12-78 was so happy and had an amazing time. It was a life-changing experience from start to finish and I'm already thinking about when we can go back. In the meantime, Sarah and Hannah are helping us with smaller trips to Europe and the Caribbean. Also, it's worth noting that in addition to both being exceptional travel professionals, they are also personable and lovely ladies who make planning calls part of the fun. I only wish I had found them sooner!"

Villas: The joy of being under one roof

For larger families, a villa stay can be absolutely perfect. One of our favourite multi-generational trips involved a family of eighteen travelling to Sicily together and staying at Villa Don Arcangelo all'Olmo through The Thinking Traveller. The villa gave everyone space to relax while still allowing the whole family to spend time together.

Our advice for this trip was to give the couple being celebrated a few nights in a luxury hotel before the rest of the family arrived.

They stayed at Belmond Grand Hotel Timeo in Taormina first, arriving at the villa rested, acclimated to the climate, and ready to welcome their guests.

Little touches like this make a huge difference.

When planning villa holidays, we also recommend thinking about a few practical details. If toddlers are travelling, check whether the villa has bathtubs. Many European villas only offer showers, but we can arrange small baths when needed.

Location is another important factor. Many larger villas are in more rural settings, so we often turn the journey into part of the experience, stopping for long lunches, wine tastings, or farm visits along the way.

One trick we suggest is making a wish list for the property. Write down ten things you would love the house to have and mark three as non-negotiable. It’s rare to find a villa that ticks every single box, but this helps prioritise what matters most.

And one rule we always recommend? A chef and housekeeping team are essential. No one wants to spend their milestone birthday debating who is doing the dishes.

"Sarah planned and organised our families (wife, me and our 3 daughters) recent incredible holiday to South Africa. This is the 3rd time we have used Sarah and she is absolutely brilliant to work with. Her suggestions were uniformly excellent and led to her creating an exceptional itinerary across 3 locations (Cape Town, Wine Region & exceptional safari in private game reserve near Kruger) with every little thing carefully planned for. Everything went like clockwork and we were left with photos and memories of the best holiday of our lives. We can't wait to start planning the next one with Sarah!"

Hotels that work for every generation

Sometimes families prefer the flexibility of a hotel, and there are a handful that do multi-generational travel exceptionally well.

Ikos Resorts are wonderful for families travelling with babies and younger children thanks to their thoughtful all-inclusive model.

Gleneagles in Scotland offers something for everyone, from falconry and golf to spa days and outdoor adventures.

Marbella Club is a long-time favourite for sunshine and elegant surroundings, while

Four Seasons Hampshire works beautifully for families wanting a countryside escape.

These properties allow everyone to spend time together while still enjoying their own interests.

Which, if we’re honest, is often the secret to family harmony.

Ski: Another brilliant multi-gen option

Ski holidays also work wonderfully for multi-generational travel.

One family we worked with travelled to Courchevel as a group of fifteen for Christmas, staying at L’Apogée Courchevel with a five-bedroom villa and two additional suites.

We arranged everything from ski school for the children and nannies for the youngest travellers to festive menus, husky sledding, flights, transfers, and New Year’s Eve celebrations.

Ski works so well because everyone can move at their own pace during the day and come together again in the evening.

How multi-Generational travel has evolved

What we’ve noticed over the past few years is that multi-generational travel has evolved quite a bit. It’s no longer simply about gathering everyone in one place for a week. Families are increasingly looking for experiences that feel meaningful, thoughtful, and memorable for every generation involved.

Grandparents often want the joy of seeing their grandchildren experience something new for the first time. Parents want the ease of knowing everything is taken care of so they can truly relax. Teenagers, perhaps surprisingly, are often the ones who embrace these trips the most when the right activities are planned. That might mean wildlife encounters on safari, learning to cook together in Italy, or sharing new experiences like skiing or sailing as a family. The most successful multi-generational trips are the ones where everyone feels included and where there is a natural balance between time spent together and space for each generation to enjoy the trip in their own way.

That balance doesn’t happen by accident. It’s something that comes from thoughtful planning and from understanding how different families travel.

Which brings us to the question we’re asked most often…

So where should you start?

If you’re thinking about planning a multi-generational trip, the first step is simply starting the conversation. Often these trips begin with someone in the family floating an idea. A milestone birthday coming up. A retirement worth celebrating. Or simply the feeling that it’s time to get everyone together somewhere special.

From there, it helps to share a few destination ideas with the family and see what excites everyone most. Confirm possible travel dates early and check school holidays, as those will often shape what is realistically possible. The earlier these conversations start, the more options there tend to be when it comes to villas, lodges, and hotels that can comfortably accommodate a larger group. It’s also helpful to get a rough sense of who is likely to come. Not everyone may be able to join for the full trip, and that’s completely normal. Some family members may only stay for a few nights, while others arrive earlier or extend their stay afterwards. Understanding the overall shape of the group helps us begin designing the trip around everyone’s needs.

Once we know who is travelling, the ages within the group, and the occasion you’re celebrating, we can start shaping the experience around the family. Because every multi-generational trip looks a little different. Some families gravitate towards the privacy and intimacy of a large villa, where everyone can stay under one roof. Others prefer the flexibility of a hotel where different generations can dip in and out of activities throughout the day, before coming back together again for dinner. Our role is to take all of those preferences and quietly bring them together into one seamless plan.

And this is also where having a travel advisor involved becomes incredibly valuable.

When you’re coordinating travel for ten, fifteen or even twenty people, someone inevitably ends up taking on the role of organiser. They’re answering everyone’s questions, chasing decisions, confirming flights, and making sure the plan is clear for everyone.

When we’re involved, that responsibility disappears. We manage the logistics, coordinate the details, and keep everyone informed so the trip runs smoothly from start to finish. It means no one in the family has to spend the entire holiday organising everyone else or worrying about whether everything is running as it should. Instead, everyone can simply relax and enjoy being together, which after all is the real purpose of the trip. Because when a multi-generational holiday is planned thoughtfully, something special happens. It’s not just another vacation - it’s something your family will talk about for years to come.

If you’re beginning to think about bringing the whole family together for a special trip, we would love to help you start the conversation.