Cheers to You!

For the fifth year in a row, WhirlAway Travel’s Jamie Jones has been named a Condé Nast Traveler Top Travel Specialist—a prestigious honor reserved for advisors with extensive expertise, trusted global connections, and a deep understanding of how to craft truly tailored journeys. It’s a distinction she’s earned through her focus on African safaris and her ability to create meaningful, insider experiences. Jamie’s philosophy is simple: “I have always believed that travel is essential for the future of our world. It connects us to nature, to different cultures, and most importantly to one another.” That approach comes to life on every African safari she curates. And that’s just one reason why she’s so exceptional at what she does. 1. She Knows Safaris Inside & Out Jamie has traveled to Africa more than 15 times over the past 12 years, earning her Signature Travel Network’s Select Safari Specialist designation—an exclusive recognition for highly vetted advisors with “feet on the ground” knowledge and proven expertise in creating luxury, customized African safaris. For Jamie, it’s about so much more than the wildlife: “I continually return because of the people I have met, friendships created, cultures I have learned from, and the peace that fills my soul with every journey.” And through WhirlAway’s Africa Apprentice Program, Jamie also helps train the next generation of safari specialists, providing extensive education and hands-on experience in planning these journeys, ensuring every client benefits from a highly personalized approach.

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.

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.”

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!

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.

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.

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.

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.