More families than ever are bringing grandparents, parents, and children together for extraordinary holidays. What was once rare—three generations sharing luxury escapes and unique experiences—is now a growing trend. From vineyard retreats to African safaris, these shared adventures are creating lifelong memories. Belgian tour operator Caractère specializes in tailor-made trips that unite generations in unforgettable destinations, where relaxation, discovery, and family connection go hand in hand.
Parents travelling with their (adult or not) children is nothing new. What is noteworthy is that grandparents are increasingly treating their children and grandchildren to luxurious, experience-rich holidays. From exclusive safaris to boutique stays among vineyards, these trips are becoming the ultimate way to create lifelong memories together. This trend hasn’t gone unnoticed by Caractère, the Belgian tour operator specializing in tailor-made luxury travel. Where generations come together amidst olive trees and sweeping vistas – on an 11-hectare estate in the heart of the Alentejo region, where modern architecture and local traditions meet to offer pure tranquility and connection.
Multi-generational travel
A few decades ago, a luxury trip with grandparents, parents, and grandchildren was rare. Today, it’s increasingly common. Wim, managing partner at Caractère, explains:
“Baby boomers often had children relatively young, certainly when compared to their own parents who lived through the war. As a result, they’re now relatively young and fit grandparents. Travel remains a priority for many. They’ve also worked hard throughout their lives, often during times of economic prosperity. Most have paid off their homes and saved up significantly. These days, they’re focused more on experiences than possessions. Unlike their own parents who only occasionally went to the seaside, they’re seasoned travellers and love sharing that joy – and financial means – with their (grand)children.”
Amidst centuries-old trees and rolling fields in the Limousin region, this characterful country house offers peace, fine dining, and family-friendly charm.
From inheritance to experience
At Caractère, demand for multi-generational travel is growing across a wide range of destinations.
“Some families choose a charming boutique hotel in Italy, while others go all out with a full safari in South Africa. What unites them is the desire to spend quality time together and create unforgettable family memories. That’s their idea of ultimate happiness,” says Wim.
Where grandparents once saved up for an inheritance, they now more often invest in moments. The so-called “multi-generational trip” is booming. Caractère is responding with travel experiences that appeal to every generation. How about a stay in a former château in France, transformed into an elegant design hotel with gourmet cuisine and its own vineyard? Or a road trip through London and the Cotswolds, where culture, nature, and quintessential English charm go hand in hand? Ideal for curious kids, relaxed parents, and lively grandparents. At Caractère, every stay is tailored to your wishes. From spacious family rooms to charming spots where young and old feel at home.
70 is the new 50, and travel is the new gift
The baby boomer generation is not only young at heart but also generous with their time and resources. They’re no longer just giving objects – they’re giving meaningful experiences. And what’s better than discovering a beautiful destination together with your family? “We’re seeing more and more families come to us with a very specific request,” says Wim. “They want to travel together – but without compromise. Everyone needs to enjoy the experience. That’s why we plan holidays that effortlessly alternate between rest and activity, luxury and simplicity, discovery and recharging.” Imagine a Tuscan villa where grandparents enjoy a glass of red wine while the grandchildren explore the rolling hills. Or a road trip through Provence with plenty of stops for culture, gastronomy, and playtime. From sunrise yoga in Greece to evenings under the stars in the Loire Valley, complete with French cinema and local cuisine – Caractère turns every holiday into a story that connects generations. Among the vineyards and beneath the Greek sun, you’ll enjoy pure simplicity and tasteful slow living at Leeda’s Village. Authentic, home-made, and always with a view. A stylish sanctuary in the heel of Italy, where design and tradition come together in a historic country house with vaulted ceilings, refined cuisine, and its own wines.
