A Summer to Remember

September 18, 2025

WhirlAway clients say it was one for the books—and now we’re already making our goals for 2026.

“What did you do for summer vacation?” With back-to-school and back-to-business in full swing, this seems to be a favorite conversation starter in September. In celebration of our clients’ favorite trips (and there were many!), we’ve created a highlight reel so you can begin dreaming and planning your ultimate 2026 summer vacation.

ITALY 

Where:  Castelfranci, Sorrento & Capri

Why Go:  Together, these destinations create the ultimate Mediterranean trifecta—savor fine wines, bask in coastal elegance, and revel in Italian dolce vita.We’re talking about Castelfranci’s rolling vineyards, Sorrento’s cliffside glamour and sweeping Bay of Naples views, and Capri’s iconic blue grottos and chic boutiques. 

Not to Miss:  The annual Castelfranci Wine Festival is held in early August and celebrates the town’s winemaking traditions with tastings, local producer showcases, food pairings, and entertainment. Excelsior Vittoria is “a favorite hotel of all time,” says one WhirlAway client. Other musts: a hands-on pizza making class in Sorrento, and a private yacht excursion around Capri curated for family members of all ages. 


ICELAND 

Where:  The Southern Coast

Why Go:  Home to the earth’s largest glaciers, there’s no shortage of icebound experiences here! 

Not to Miss:  Hike the picturesque glacier outlet of Sólheimajökull and take in panoramic views of the surrounding mountains. Discover large sinkholes, called moulins, which drain into crystal-clear waterfalls beneath the black sand. And best of all: Explore the interior of a volcano on a journey that begins with a 40-minute hike to the crater. Once inside, you’ll be lowered into the volcanic opening with a specially designed lift. As your descent begins, the magma chamber puts on a display of magnificent colorations and eclectic textures.



CROATIA 

Where:  Dubrovnik, Hvar & the Island of Bisevo 

Why Go:  Sun-drenched days along the Adriatic, historic walled cities, and glittering turquoise seas make Croatia irresistible for summer adventuring. Luxury travelers will find secluded islands accessible by private yacht, Michelin-starred dining in Dubrovnik and Hvar, and boutique hotels carved into centuries-old stone palaces. 

Not to Miss:  When in Croatia, a boat tour on the Adriatic Sea is basically mandatory! Explore some of the bluest waters and take in the renowned sights between Dubrovnik and Hvar. While exploring the island of Bisevo, be sure to visit the large Monk Seal Cave—named after the Mediterranean creature who used to reside on its beach. And on Vis Island, Stiniva is one of the most Instagram-worthy beaches in all of Croatia.



HAWAII 

Where:  Kona & Maui 

Why Go:  Pristine beaches, dramatic volcanos, lush rainforests, and lavish resorts. Indulge in culinary journeys of hyper-local flavors and discover where culture meets nature—whale watching, private sailing, and star-gazing from volcanic heights. 

Not to Miss:  An evening manta ray snorkel—the most famous scuba dive or snorkel in Kona. A shallow, 25-foot depth allows both snorkelers and certified divers to get in on the action, as these gentle giants feed on a buffet of plankton attracted by dive lights. On Maui, the Haleakala Sunrise Guided Bike Tour takes you to the 10,000-foot summit of Haleakala, where you’ll learn about its significance in Hawaiian culture. As you enjoy bi-coastal views of Maui's central valley and the West Maui Mountains, you’ll spin through Maui’s most enchanting landscapes.



ALASKA

Where:  An indelible cruise through the waters of Alaska with National Geographic-Lindblad Expeditions. 

Why Go:  There is no place quite like this—an untrammeled frontier of snow-capped mountains, breathtaking fjords, and extraordinary wildlife. Lindblad Expeditions has been exploring the region’s wildest corners for more than 40 years, seeking out inlets and coves where larger ships can’t sail.

Not to Miss:  Glide among electric blue icebergs, hear the thunder of calving glaciers, and cruise shore-ward in Zodiacs for sightings of brown bears, pods of orcas, breaching whales, and bald eagles. When in Glacier Bay National Park, learn from First Nations peoples in Haida Gwaii, walk rainforest muskegs, or journey through the seldom-seen coastal inlets.



GREECE

Where:  Anywhere you can island hop from   your own private yacht!

Why Go:  Imagine a trip for a family of six, including all ages and travel preferences. Add milestone moments like a retirement celebration, a son’s 30th birthday, and a daughter’s graduation, and this Greek sojourn will quickly become a favorite summer vacation. 

Not to Miss:  A beach club day at Scorpio’s on Mykonos, a biking excursion on Ios, and dancing with the yacht crew during your last dinner aboard. A happy WhirlAway client can attest: “It’s the easiest, most relaxing, and best quality family time they’ve ever had—a very special vacation!”



A Roar-Worthy Safari Specialist

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.

Multi-Gen Magic

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.

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!
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