Where to Spend the Holidays: Luxury Winter Escapes Worth the Flight
From festive European cities to sun-drenched beaches, here’s where Travel Well recommends for unforgettable holiday travel—and why now is the best time to start planning.
Why You Should Plan Your Holiday Vacation Now
If you’re dreaming of a luxurious winter escape, the time to start planning is now. From late November through New Year’s, the world’s most sought-after destinations fill up fast—especially premium flights, private guides, and tailored experiences. Early booking ensures better availability, more customization, and access to the most exclusive holiday events.
Whether you crave snow-dusted charm or a sunny shoreline, Travel Well has curated a list of luxury holiday destinations that are well worth the flight.
Vienna, Austria
A Storybook Christmas Come to Life
Vienna is pure holiday magic—filled with historic charm, twinkling lights, and the melodies of Mozart echoing through grand concert halls. Its Christmas markets are legendary, and its atmosphere is perfect for couples or families seeking old-world elegance during the holidays.
What to See: Explore the Christmas markets at Schönbrunn Palace and Rathausplatz, visit the grand Vienna State Opera, and admire the seasonal lights on the Ringstrasse.
What to Eat: Sip Glühwein while snacking on roasted chestnuts and traditional Sachertorte. Don’t miss the buttery Vanillekipferl cookies at market stalls.
St. Moritz, Switzerland
Snowy Sophistication in the Swiss Alps
St. Moritz is the pinnacle of alpine luxury—offering a glamorous mix of powdery slopes, designer shopping, and dramatic mountain views. It’s perfect for discerning travelers who love skiing by day and champagne toasts by night.
What to See: Ride the Bernina Express for panoramic alpine views, skate on frozen Lake St. Moritz, and take in world-class art galleries tucked into the mountainside.
What to Eat: Warm up with creamy Swiss fondue, crispy Rösti, and a slice of Engadin Nusstorte, a rich caramelized walnut tart native to the region.
Maldives
Barefoot Luxury in the Indian Ocean
For those who’d rather skip the snow, the Maldives delivers turquoise waters, white-sand beaches, and total serenity. Perfect for honeymooners, families, or anyone wanting sun and seclusion over the holidays.
What to See: Snorkel vibrant coral reefs, take a sunset cruise aboard a dhoni, and explore the local island culture beyond your private villa.
What to Eat: Feast on fresh-caught reef fish, tropical fruit, and coconut-rich Maldivian curries. Enjoy oceanfront dining under the stars.
New York City, USA
Classic Holiday Magic with a Cosmopolitan Edge
There’s nothing quite like New York during the holidays. The city comes alive with sparkling lights, iconic events, and an infectious sense of joy. Perfect for families, couples, and solo travelers who want an iconic winter experience.
What to See: Visit the Rockefeller Center tree, window-shop along Fifth Avenue, and enjoy the Rockettes at Radio City. Ice skating in Bryant Park is a must.
What to Eat: Indulge in festive pastries at traditional bakeries, sip on thick hot chocolate, and savor classic New York pizza or bagels between holiday events.
Tuscany, Italy
A Cozy Countryside Escape
Trade the crowds for the calm of Tuscany, where rolling hills, stone villages, and vineyard-lined roads offer a slower, more meaningful way to spend the holidays. It’s romantic, relaxing, and full of seasonal flavor.
What to See: Wander the medieval towns of Siena and Montepulciano, visit working olive oil estates, and enjoy scenic drives through the Chianti region.
What to Eat: Enjoy winter favorites like ribollita (Tuscan bread soup), handmade pastas with truffle, and finish with panforte—a spiced fruit and nut cake that dates back to the Middle Ages.
French Polynesia
Tropical Tranquility for the Holidays
For those dreaming of a barefoot Christmas, French Polynesia offers a peaceful retreat with luxury woven into every moment. Think crystal-clear lagoons, lush mountains, and unmatched natural beauty.
What to See: Swim with rays in Bora Bora, hike to waterfalls in Moorea, or enjoy a Polynesian dance show by torchlight.
What to Eat: Taste poisson cru (Tahitian-style ceviche), grilled mahi-mahi, and fresh coconut-based desserts. Enjoy tropical fruit picked fresh from the tree.
Make the Holidays Your Most Luxurious Trip Yet
Holiday travel is about more than a change of scenery—it’s about creating lasting memories in extraordinary places. Whether you’re drawn to festive cities in Europe or barefoot beaches in the tropics, Travel Well will help you plan a seamless, personalized winter getaway.
Let us take care of the details. Now is the time to reserve premium accommodations, secure your ideal flight routes, and lock in unforgettable experiences.
Ready to plan your holiday escape? Contact Travel Well to get started today.