If there is merit in Ralph Waldo Emerson’s observation, “Life is not a destination, it’s a journey,” then the 19th century philosopher was well ahead of his time. Today, there’s a sea change around trip purpose that aligns with the rise in demand for multigenerational vacations. It’s not just about where to go…but why. At luxury travel specialist Black Tomato, Co-founder Tom Marchant puts it succinctly, “A lot of people don’t actually know where they want to go, but they know how they want to feel.”
Tailored Trip Planning for Families
Actually, it’s about how the whole family wants to feel…including the kids, the parents, and increasingly the grandparents, too. Who goes on a journey together is paramount to its shared purpose. Because a family comprises the most important people in the world, bespoke tour operators take personalized planning approaches to multigenerational travel.
Knowing that each family member wants to feel fulfilled during time spent away from home, there’s a lot of planning required to please everyone. That means maximizing engagement for younger travelers while also giving adults opportunities to relax. More and more families are taking advantage of combining shared quality time with educational real-life adventures for the kids. Ultimately, memories made together are what matter most.
Pursuing a New Approach to Travel
Who said machines don’t have a heart? At Black Tomato, the brand new ‘Pursuit of Feeling’ platform redefines tailored trip recommendations by embracing a fundamental shift away from destination-driven choices to emotional ones. Travelers activate this approach by expressing how they want to feel and the AI-augmented technology supported by (very) human insights will match desired feelings with places. In collaboration with travel experts, this approach fine-tunes the destination that will best deliver.
Each and every Black Tomato trip is then personally tailor-made with a bespoke itinerary to align with the desired vibe among five emotional pillars: revitalized, distraction, challenge, freedom, or contentment. For instance, The Feelings Engine might suggest India for revitalization, Mongolia to feel distraction, or Greenland for adventure by challenge-seekers.
After two decades of creating and operating bespoke luxury trips, Black Tomato draws on extensive experience. Marchant observes, “We’ve always focused on the emotional drivers of travel, asking clients why they want to travel before landing on a destination. With the ‘Pursuit of Feeling,’ we’re amplifying this foundational approach in ways that feel more personal and meaningful than ever before.”
Feeling Freedom in Atacama Desert
For mountains, moonscapes, and star-scattered skies—Chile, anyone? If you—or the kids—have ever wondered what it might feel like to transport yourself to another planet (travel to Mars aside), Black Tomato suggests a pursuit of feeling experience in Chile’s Atacama Desert, a surreal landscape that’s the driest place on earth. Climb into the basket of a hot air balloon to watch the sun rise. Hang out with flamingos on the Chaxa Lagoon. Marvel at the ancient Tatio Geysers ringed by volcanoes. Go glamping beneath the stars high in the Andes. The barren and breathtakingly beautiful place is illuminated by the Milky Way, evoking an otherworldliness, a deep sense that this is what freedom feels like.
Feeling Contentment on the Aegean Sea
For fresh seafood, pine forests, and sun-bleached coves, slip into a slower pace of life in Greece, suggests Black Tomato. “If your dreams are colored by zigzags of blue-white houses, fragrant olive groves, pretty fishing villages, and visions of a balmy Aegean Sea,” dreamy Greece is what contentment feels like. An epic family odyssey awaits. Just imagine showing the kids the ancient cave of Zeus, the birthplace of Aristotle, and the Skopelos beach where Mamma Mia! was filmed. You’ll want to sail on a private boat with your own skipper and chef to the hidden island of Folegandros, to savor a culinary market tour of Mediterranean flavors in Thessaloniki, to get exclusive access for a sunset tour of the Temple of Poseidon.
Inspired By the Mind of a Child
With the demand for multigenerational travel growing, children are taking an active role in the trip-planning process. After all, the next generation is building a love of travel while creating nostalgic sentiment for future return visits.
Inspired by the mind of a child, luxury adventure company Pelorus introduced ‘Imagine This.’ The new service builds on Pelorus Junior, launched in 2024, which provides Junior Adventure hosts and parallel itineraries for young travelers on family trips. ‘Imagine This’ invites children to share their wildest vacation dreams, from which Pelorus designs experiences just for them. The concept gives kids the opportunity to become involved at the earliest stage of the planning process, staying engaged throughout the trip.
Some favorite sample travel itineraries for families include a yacht treasure hunt in the Bahamas inspired by pirate “Calico Jack” Rackham, including encounters with the island’s swimming pigs. Another is a Family Summer Adventure through Norway with ziplining, a Viking village encounter, and fjord adventures. For a safe and hassle-free holiday that incorporates hobbies and interests, kids can explore with their own knowledgeable Junior Adventure Host.
It’s Never Too Soon to Plan Ahead
“The earlier a family starts planning their trip, the better,” says Jimmy Carroll, Pelorus co-founder. “It gives them access to the most exclusive experiences and accommodation options to make their experience truly extraordinary. Though, Pelorus has been known to turn around a show-stopping family vacation in 24 hours. Designing such a memorable trip is a fun experience for families too, so planning early will give the whole family lots to look forward to as their pre-travel excitement builds.”
Photos courtesy of Eclectic Travel for Black Tomato and Pelorus
Noting the trending demand for multigenerational deluxe vacations, luxury travel advisor Virtuoso works with Black Tomato, Pelorus, and others on multigenerational trips that require a high level of attention to detail. Because the travel industry is riding a wave of elevated demand for ultra-luxury vacations, six-figure getaways have become standard for a small but growing segment of travelers.