A Peek Inside the Trips We Take for You

June 19, 2026

From Antarctica to Africa, Egypt to Ecuador, Japan to Jordan, the WhirlAway team has taken educational trips to more than 30 continents and countries, cruised with more than a dozen river and ocean lines, toured hundreds of hotels, and spent countless hours exploring the places our clients want to travel. 

Why? Because no amount of research can replace firsthand knowledge. “Experiencing a destination with all senses gives our advisors a unique perspective to better guide a client toward what’s right for them,” says Jamie Jones, WhirlAway Travel’s President and Luxury Travel Advisor.


These educational trips are far from vacations. During a recent visit to Greece, Alison Warner stayed at five hotels and visited 20 more—taking detailing notes, photographing rooms and public spaces, and building relationships with hoteliers and concierges along the way. Often, our advisors travel alongside trusted in-country partners, allowing them to evaluate every element. “We see firsthand the quality of the guides, cars, drivers, and the experience itself,” notes Sara Samuel, Vice President and Luxury Travel Advisor. “It’s about learning all the little nuances.” Here, we share eight such nuances that make all the difference.


1. We know how the service truly feels.
It’s so much more than formal versus casual, stuffy versus friendly. We know if a specific hotel’s room service will deliver your cappuccino in five minutes or in 35 … if the concierge will remember your name after day one or if you’ll always be a room number … if the staff is genuinely happy to serve you or simply going through the motions. 



2. We know the difference between a location and specific locations within that location.
For instance, staying along the Grand Canal in Venice is fantastic … usually. That’s because there are many locations within this area—and each varies greatly. In some spots, you’ll be right on the water and it will feel like your family has it all to yourselves. In others, there will be a crowded promenade between your hotel and the water, your view always blocked by passerby. There’s a big difference, and we share every bit with clients.


3. We know how easy or challenging it is to get around a destination.
Of course we provide seamless arrangements, but we can’t control the traffic flow, the quality of the roads, or an airport’s efficiency. In more remote destinations or developing nations, this is particularly important so we can manage expectations and prepare clients for travel.



4. We know what a curated tour or experience is really like.
Private cheese-making … horseback riding to a mountaintop picnic … sunset sail. They all sound spectacular but it’s the tiny minutia that can transform something great into “holy-sh*t-that-was-the-most-incredible-thing-I’ve-ever-done!” Take, for instance, a visit to a Venetian atelier where you dress up in vintage costumes. Sounds a bit cheesy, yes? That’s what we thought—until we experienced it ourselves with an incredible guide. Now it’s something we recommend to the right client, but only with this particular guide who knows exactly how it should be done.


5. We know that not every five-star hotel is equal.
There are many hotels that are technically five-star but don’t feel very five-star when you actually stay there. Take, for instance, the beautiful five-star resort at the bottom of the Taormina hilltop in Sicily. It’s just a short walk from the cable car that whisks you up the cliffside to the historic town center. But we recently discovered the short walk is on a busy road with almost no sidewalk (have you seen Italian drivers?) and the cable car station is much like a bus stop—there’s nothing luxurious or charming about it. We have the perfect alternative. 



6. We know who the other guests will likely be.
We can tell you if your traveling neighbors will be predominantly American or international. There’s nothing wrong with either as the preference depends on the individual client. Let’s say you're visiting a beach resort: Who do you want to be lying next to you at the pool all day? It’s little things like this that matter, and we get it.


7. We know that timing is everything.
Yes, a site or landmark feels different depending on when you visit, but it’s so much more than what season or what month. Oftentimes, it comes down to the very hour. Case in point: the famous cathedral in Orvieto, Italy, its façade bedecked in gold mosaics. Visit when it’s shaded and you’ll find it lovely, but visit when it’s hit directly by the sun and glistening in all its golden light? An incredibly magical, jaw-dropping sight. 



8. We know how to cut through clutter and fake content.
In this day and age of information overload, research fatigue is more prominent than ever, while AI can make it difficult to know what’s truly real. But not for us—because we’ve been there in real life. That means we can provide certainty, peace of mind, and photos that we know are not altered. 


June 9, 2026
As Greece seems to once again headline our summer travel conversations, one question remains: Where should you stay?
May 11, 2026
Since 2022, WhirlAway Travel’s Anna Dunleavy has been crafting epic getaways for the Creed family—each one more personalized than the last.
April 20, 2026
Grand Slam tournaments are the crown jewels of tennis—and notoriously elusive to access. Tickets disappear instantly, VIP passes are closely guarded, and logistics can be overwhelming. That’s where WhirlAway comes in—with guaranteed seats, exclusive perks, and insider access to the world’s most prestigious matches.
April 15, 2026
There’s something extra meaningful about pairing a dream destination with a milestone moment. For WhirlAway’s Denise Booth, that meant finally experiencing Australia alongside her son as they celebrated his graduation from medical school.
April 3, 2026
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.
March 20, 2026
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.
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.”
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!
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.
More Posts