The Awestruck Edit
When Should You Plan 2026 Holiday Travel? (Hint: Sooner Than You Think)
You may not want to think about more snow…but now is the time to start planning your 2026 holiday travel.
Late November through early January are some of the busiest weeks in travel. Demand peaks around the holidays, and the very best experiences are typically booked months in advance.
Planning early is essential to securing the ideal festive journey: that one city suite with the view, the micro-resort in the Arctic, or a tropical villa to fit the entire family on Christmas morning.
The festive season is also one of the most complex times of year to navigate. Flights fill, availability tightens, and logistics become less forgiving. Waiting often means compromising.
Whether you dream of trading white snow for sun-soaked sand or leaning fully into the season, we’ve curated a selection of our favorite destinations below to spark ideas – and show what’s possible when you start planning early.
Chasing the sun…
For those ready to trade winter cold for warmth and outdoor adventure
Los Cabos, Mexico
Desert meets the rugged Pacific Ocean in one of Mexico’s most polished destinations, where private villas, ultra-luxury resorts, and world-class dining make for an easy but luxurious festive escape
Ask your advisor which properties have the most coveted balconies for whale-watching
Costa Rica
An adventure-lover’s playground, where jungle lodges tucked away in lush tropical rainforests collide with stunning beaches for days that move seamlessly between adventure and relaxation
Ask your advisor about exclusive tented camp stays with private air transfers
Ecuador & the Galapagos
A bucket-list festive trip, spent traveling by small ship, encountering extraordinary wildlife, and exploring one of the world’s most unique ecosystems respectfully under the guidance of an expert naturalist
Ask your advisor which small-ship expeditions have the best naturalists and landing access
…Or Embracing the Season
Christmas Markets
Sail through storybook towns along the Danube or Rhine, where twinkling markets, mulled wine, and centuries-old traditions create an effortlessly festive experience
Ask your advisor which line has the most immersive multi-country itineraries
Arctic Landscapes
Celebrate the season in Scandinavia under the aurora borealis, with husky sledding, cozy lodges, and the remote beauty of the far North
Ask your advisor about glass igloo stays, remote lodges, or how to wow the kids with a visit to Santa’s village
Alpine Skiing
From Courchevel to St. Moritz, festive travel in the Alps means world-class skiing and refined alpine villages (made complete by holiday-themed après)
Ask your advisor where to find the best ski-in/ski-out chalets with full staff, or the leading ski resorts
What’s Your Vision for Holiday Travel in 2026?
Whether you’re dreaming of waking up to the sound of crashing waves on Christmas morning or toasting in the New Year in a Veuve Clicquot yurt on the slopes, the most memorable holiday travel for 2026 requires thoughtful planning, well in advance.
If something here sparked your interest, now is the time to begin the conversation.
Introducing Client Chronicles
Seeing our travelers experience the world in unforgettable ways is one of our greatest joys. To celebrate your journeys, we are launching Client Chronicles, a new feature in our monthly Travel with Awestruck newsletter and blog where we invite our travelers to reflect on their greatest adventures.
Italy with the Vecchiones
Joann and John Vecchione have been traveling with Awestruck since 2018 throughout Mexico, the Caribbean, and Europe. In early October of 2025, they set off on a couple’s trip across Rome, Florence, Tuscany, and the Amalfi Coast.
Joann was convinced that this would be the couple’s only trip to Italy and instructed Jenene to design it as such, but recalling that moment, she shared, “Jenene told us this would be our first trip to Italy but would definitely not be our last. And she was so right!”
We asked Joann to think back to the most unforgettable moments of her trip (“Wow! There were so many incredible moments it’s hard to say”). The memories that Joann then shared had one thing in common: they centered around the Italian people.
- A cooking class in a family home – “It was such an amazing day. The family was so inviting, and not only did we have a delcious meal, but we also got to know the family and how they live.”
- A guide who became a friend – “When we visited Pisa, we again had the most amazing driver, and we invited her to have lunch with us. She shared so much about her life.”
- A warm personal welcome – “Eden Roc in Positano was outstanding. We were treated like royalty. Every morning we were greeted by Tony.”
“We hesitated when Jenene suggested private tours would be best for us,” Joann reported, “But in the end, I would not do it any differently.”
The Vecchiones reported exceptional stays – from Eden Roc to the Brunelleschi – but they focused on the people as much as the properties: “They were all so friendly and kind. My husband commented that even when people are mad, they don’t act mean or rude in Italy.”
Joann and John are already planning their next trip, “We will be visiting Italy again, soon this time: Milan, Venice and Lake Como.” Their advice for future Italy travelers?
“Don’t skimp – eat the food, drink the wine, and definitely have gelato or a pastry daily! Enjoy it all! The only regret we have is that we should have stayed longer. So guess what, Jenene was right, and we’ll be back soon!”
What will your next story be?
Whether it’s an upcoming European summer escape, a company retreat you can’t stop thinking about, or a to-be-planned festive journey ahead, we look forward to partnering on your next adventure.
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