Multi-Gen Magic
Epic and easy travel for all—even toddlers and grandparents? That’s the WhirlAway touch.
Multi-generational travel is booming—and it’s easy to see why. Families are seeking curated journeys where every generation—from grandparents to grandchildren—can experience the world together, yet on their own terms. At WhirlAway Travel, that means private excursions, seamless logistics, and experiences that let everyone focus on what matters: connection.
Denise Booth is one of WhirlAway’s multi-gen travel experts. She leverages her insider access and relationships with global partners to create itineraries perfectly suited for every age and interest. “Travel does not have to be all or nothing,” she says. “We craft experiences that can be enjoyed by each person, from modified activities or alternatives for those who cannot participate.” Here are three recent journeys planned by Denise and the WhirlAway team.
A Luxury Family Escape to Greece
The Travelers: Ten family members, ages six to 77—parents, daughters, husbands, and four grandchildren—living in three different states!
The Perfect Choice: The grandparents were celebrating their 50th anniversary and wanted to do something really special for the whole family. With a love for the water, they envisioned boating as a centerpiece of their trip, and needed accommodations spacious enough for everyone.
Epic Experiences: A full-day cruise from Paros to Antiparos aboard a luxury yacht included sailing to stunning sea caves and cliffs, with options for swimming, cliff diving, snorkeling in the Blue Lagoon, or simply relaxing on deck. In Crete, Denise arranged a private market visit to taste local cheeses and olives, followed by a hands-on cooking class in Chania. At the end of the day, the whole family sat down together for a delicious meal paired with local wines.
The WhirlAway Advantage: Relationships with trusted local providers allow the team to accommodate mobility needs and dietary preferences. WhirlAway remembers every detail and loves surprising clients. During the initial consultation with this family, Denise learned their favorite wines—and planned ahead, arranging with the chef to surprise them with the same varietals during their family meal in Chania.
Wine, Food & Family Time in Italy
The Travelers: Eight family members, ages one to 72—parents, adult children, spouses, toddlers. The thought of international travel with toddlers was initially daunting, but Denise knew how to make it effortless.
The Perfect Choice: This family wanted a change from their usual summer beach vacation. They dreamed of a destination none of them had visited and a private home where everyone could relax together. Their wish list included great food and wine, a bit of history, and plenty of down time at a property with a pool, private chef, and ample space. We knew exactly where to send them: Tuscany!
Epic Experiences: A winery tasting and cooking class—at a WhirlAway secret gem—were combined into a single day, with the kids included in the culinary fun. Knowing the father was a big Stanley Tucci fan, Denise tapped her local connections to create a personalized Florence experience, complete with visits to insider spots.
WhirlAway’s Special Touch: At the end of their day at the winery, the family was surprised with a keepsake bottle of wine, complete with a custom label—a small, thoughtful detail that captured the spirit of their Tuscan adventure.
Family Adventure & Impact in Africa
The Travelers: Six family members—grandparents, parents, two grandchildren, including one celebrating a high-school graduation.
The Perfect Choice: WhirlAway President Jamie Jones had recently returned from Kenya with Micato, where she co-hosted a webinar. Inspired by what he saw, the grandfather decided it was finally time to travel to East Africa—the perfect way to celebrate his grandson’s graduation.
Epic Experiences: This active family thrives on adventure, so Jamie started them off with a hike through Nairobi’s Karura Hills and ended with a mountain gorilla trek in Rwanda. Along the way, she planned custom safaris and a private visit to the America Share Harambee Community Centre to see the positive impact their travels have on local children.
How WhirlAway Saved the Day: Less than 24 hours before departure, the airline canceled their flight. All six travelers were booked in business class and didn’t want to downgrade. WhirlAway knew how to pull some strings behind the scenes and secured last-minute business-class seats on another airline. “We know Africa,” says Jamie. “And we also know how to navigate when things go awry!”
