’Tis the Season for Travel!

December 15, 2025

It’s that time of year when festive getaways are all the buzz, and this holiday season is a great time to start thinking about next year’s greatest escapes.

 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!

Who:  A mother and her two teens.

 

Client Wish List: A warm-weather destination offering nature, adventure, wildlife, and a sense of culture. 


Where To:
They chose Costa Rica because it checked all the boxes. Wanting a mixture of different experiences, hotels, and geography, WhirlAway selected three unique Costa Rica stays: 1) Pacuare Lodge, known for its immersive rainforest experience, Indigenous cultural experience, waterfall hikes, and amazing white-water rafting. 2) Hacienda Alta Gracia, an Auberge Property and luxury retreat set on a 180-acre estate with the perfect blend of nature, equestrian experiences, and world-class spa treatments. 3) Arenas Del Mar. a luxury eco-resort that combines rainforest and beach. It’s also excellent for wildlife viewing, relaxation, and adventure. Located on the Edge of Manual Antonio National Park, it offers a catamaran and snorkeling tour, the private Manuel Antonio National Park Tour, hiking, wildlife, and private surfing lessons. 


The Why:
The mother chose to work with WhirlAway for one very simple reason: “You know what we like!” she said.


Who: An adventurous, active couple.

 

Client Wish List: They always wanted to experience Antarctica, and initially, began planning the trip on their own. They decided to work with WhirlAway for more insider knowledge and expertise in the area.

 

Where To: The proverbial “polar plunge,” cruising south with Abercrombie & Kent. Not your typical Antarctic cruise, this experience involved venturing off the beaten path, with visits to South Georgia and the Falkland Islands. 


The Why:
  Antarctica topped their lifelong bucket list!

Who:  A family of six, including four younger adults, who wanted a warm-weather escape to beat the midwinter blues.

 

Client Wish List: Warm and relaxing was the order of the day, but with active pursuits (hiking, boating, water sports) on tap, too. Additionally, they wanted to stay in a house rather than a hotel.

 

Where: They landed on Turks & Caicos because it allowed for a non-stop flight, a private home stay, plus beautiful beaches. Villa Alexis on Chalk Sound was just what they were looking for.

The Why: This family had worked with WhirlAway previously on a family trip, and were confident in a seamless travel experience. They wanted an island that was easy to navigate, and with plenty of dining options. They knew WhirlAway would know how to match what they were looking for in both a destination and accommodation.

Who: A multi-generational group vacation for 10 travelers, including grandparents and their two daughters’ young families (with kids ranging in age from 10 to 18). The grandparents had always wanted to travel to Africa, and decided that now was the perfect time to go.

 

Client Wish List: One of the daughters follows the Motherchic on Instagram and was interested in a similar safari experience, so she referred her parents to WhirlAway. Comfort, safety, and excellent wildlife viewing were important, as were five-star accommodations.

 

Where To: South Africa, including a boutique hotel buy-out in Cape Town; Tswalu at Tarkuni villa; and a final stay at Waterside Royal Malewane in Thornybush Private Game Reserve to witness the Big 5. The itinerary was the perfect mix of city and safari, with exclusivity emphasized throughout. 


The Why:
South Africa is the perfect country to experience as a family. There’s something for everyone, and for grandparents to experience the wonder and awe of safari with their grandkids is truly special. South Africa is also relatively easy to get to, while traveling within the country is also easy. WhirlAway is best known as safari experts, with nearly 20 visits collectively by the team. We know how to execute the trip of a lifetime! 

Who: A family of four, including parents and their two college-aged children. 

 

Client Wish List: They requested a short-notice trip to London during Festive season (after Christmas). They wanted to see the typical sites, but with expert local guides who could share authentic stories and lesser-known bits of history. The Churchill War Rooms, “Behind The Glass” (live performers placed inside window-style displays), and a walking food tour of Spitalfields Market were trip highlights. 

 

Where: Central London—a safe, walkable location where the kids could explore on their own. WhirlAway recommended a five-star, luxury boutique hotel for its charm, location, excellent daily breakfast (included, thanks to WhirlAway’s Signature Travel Network partnership), and commitment to exceptional service. They stayed in a two-bedroom suite and were amazed by how special the entire staff made them feel.


The Why:
The parents wanted to give the kids a memorable introduction to Europe, starting with London. They found it daunting to plan a short-notice getaway, especially during Festive season, and wanted to make the most of their vacation together. They had never used a travel advisor before and were thrilled to have everything planned for them (hotel, transfers, private guides, insurance, etc). They said their entire experience, from initial consultation to their private transfer home from the US airport, exceeded their expectations. WhirlAway is currently planning their next big family adventure to Italy!


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, 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.
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.
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.
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.
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.
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.
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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