Multi-Gen Magic

March 20, 2026

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, WhirlAway’s multi-gen travel expert, 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!”

Just Back From … Japan with WhirlAway’s Stacey Blum

March 11, 2026
Why Japan & Why Now The neon-lit energy of Tokyo, the zen temples of Kyoto, and the restorative calm of mountain onsen towns define this unique journey across time. “It’s a place that feels both ancient and futuristic at once,” Stacey says. Japan also rewards travelers who slow down. For Stacey, early mornings—what the Japanese call the “blue hour”—were especially poignant. Known as the time just before sunrise or after sunset when the sky turns a deep indigo, the serene, otherworldly atmosphere is the perfect window for photography in cities like Tokyo and Kyoto, capturing the magical light over temple roofs, as locals cycle along rivers, and as shops open their doors. To fully appreciate Japan’s diversity, Stacey recommends giving yourself at least 10 days in the destination (plus two days of travel) and visiting three distinct regions. Stacey’s Takeaway: “Japan is not a place you try to see it all in one trip. It’s somewhere you’ll want to return to again and again.”

Sail Beyond the Expected

February 17, 2026
No summer travel plans yet? Consider this your fast track to an experience that ticks all the boxes for value, ease, culture, scenery, and laid-back luxury. What: A seven-night Mediterranean cruise aboard Silver Nova with Silversea and Signature Travel Network. Where: Roundtrip from Athens, visiting seven ports throughout Greece and Turkey. When: August 16-23, 2026. Why: It’s a remarkable blend of epic history, island charm, and elegant cruising. You’ll visit spots that feel straight out of a postcard, from the delightful seaside town of Gythion and the Olympic roots of Katakolon to Santorini’s bucket-list sunsets and the lively markets of Bodrum. Onboard, the suites are beautifully spacious, the butler service is effortlessly attentive, and the all-inclusive approach is indulgent yet smart, inviting you to savor the experience without a second thought. Yes, please!

Just Back From … Northern Italy with WhirlAway’s Sara Samuel

February 12, 2026
Recently back from an immersive journey through Verona, Venice, and Trieste, WhirlAway’s Sara Samuel discovered a trio of destinations that feel worlds apart yet effortlessly connected. From Shakespearean streets and quaint canals to culture shaped by shifting borders, this is Italy beyond the expected.

Just Ask Jamie …

January 21, 2026
Why stay home for the holidays when you can discover chocolate, castles, and Christmas decorations across Europe? That’s just what WhirlAway’s Jamie Jones had in mind when she took her family on a holiday river trip through Amsterdam, the Netherlands, Brussels, and Antwerp. Here’s what happened along the way.

2026 is the Time!

January 14, 2026
If “someday” is starting to sound suspiciously like “never,” this is your sign. From polar ice to private yachts, safaris to southern skies, these six monumental journeys are proof that the best trips happen when they’re meticulously planned with insider expertise.

Just Back From … Italy’s Puglia Region

December 15, 2025
Nestled in the heel of Italy, these spots have long been Italian favorites and are now drawing travelers from around the world. But visit in the fall or winter, and it still feels like you have them all to yourself. Sara says it was nearly impossible to choose favorites—and she could easily share dozens more—but here are the places and experiences she loved most.

’Tis the Season for Travel!

December 15, 2025
In 2025, WhirlAway planned dozens of amazing vacations for the holiday season, and we’re sharing a few of our favorites. Consider this your cheat sheet to the dreamiest destinations, including a sun-kissed sojourn to Costa Rica, a multi-gen escape to South Africa, an Antarctica cruise, and the best of Turks and Caicos, and London. Happy holidays, and even happier travels!

Just Back From … the Cycladic Islands

November 18, 2025
What makes the Cycladic Islands feel so singular? For Luxury Travel Advisor Denise Booth, it’s the blend of warm hospitality, luminous landscapes, and quietly luxurious living. Fresh off her journey through Naxos, Paros, and the Athenian Riviera, she shares three experiences that showcase Greece beyond the guidebooks—intimate, delicious, and endlessly photogenic.

Greece: Wellness Capital of the World

November 17, 2025
Luxury Travel Advisor Stacey Blum is our expert in all things wellness. Before joining the WhirlAway team, she worked as a health coach and is now a Signature Travel Expert Select in Wellness. And her favorite destination for wellness, in every sense of the word, is Greece. While she’s visited the country three times (and counting), she’s planned so many trips for clients that she says it feels like she’s been there dozens of times: This past summer alone, she curated 12 different trips! “Every part of Greece—the food, the water, the people—invites you to take a deep breath and just be,” she says. “You come here for a break, but you leave with a lighter heart, a clearer mind, and a deeper sense of gratitude.” Here, Stacey shares how the beautiful country is a master in the art of slowing down.
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