Your Ultimate Winter Travel Guide

Unlock the Magic of Winter in These Captivating Destinations

Your ultimate winter travel guide for 2023 is here! If you’re like us, this summer heat may have you daydreaming about cooler weather, nostalgic holiday traditions, and snowy escapes. Thanks to globally renowned Christmas markets, world-class ski destinations, and tropical destinations with perfect year-round weather, it’s no wonder December and January are one of the busiest travel periods of the year. Imagine skiing directly from your cozy lodge, wandering through the dazzling streets of New York, savoring the festive markets of Vienna and Prague, embracing the tranquility of the Swiss Alps, basking in the tropical paradise of Hawaii, or indulging in the vibrant culture of Mexico. We’ve compiled a list of 6 top-notch destinations designed to make your festive season getaway an unforgettable one.

The festive season, informally spanning from December 20th to January 4th, comes with its own set of rules during those two weeks, making it more regulated compared to other times of the year. Expect limitations such as blackout dates, minimum stay mandates, and extended cancellation policies, which might add a bit of complexity to your holiday travel plans. To ease some of the added stressors surrounding holiday travel, refer to our Festive Travel Planning blog.

Ski-In/Ski-Out Resorts

For snow enthusiasts, the call of the slopes is irresistible, and ski-in/ski-out resorts offer the perfect gateway to a winter wonderland. Picture yourself gliding down powdery trails, surrounded by towering mountains and crisp, invigorating air. Colorado, Montana, Utah, and Whistler, Canada, are just a glimpse into the world of Alpine adventure, offering not only thrilling skiing experiences but also luxurious amenities and a host of winter sports activities.

Pro Tip: If you plan on skiing in the States this winter, check out our top 5 places to ski. Of the resorts mentioned, The Little Nell, Montage Deer Valley, Four Seasons Jackson Hole, Amangani, and Montage Big Sky all offer ski-in/ski-out access. Goldener Hirsch, Auberge Resorts Collection in Deer Valley, Utah also offers ski-in/ski-out access, and Allie from Team O recapped her stay last year. The same goes for Madeline Hotel & Residences, Auberge Resorts Collection in Telluride, Colorado! Contact our team for availability during your desired dates.

A Symphony of Lights and Delights: Christmas Markets in Vienna and Prague

Step into a world of twinkling lights and festive cheer as Vienna and Prague transform into magical wonderlands during the holiday season. Lose yourself in Prague’s Old Town Square, where Gothic architecture sets the stage for handcrafted treasures and mulled wine. Vienna’s Rathausplatz is adorned with stalls offering a sensory delight of handmade crafts and tantalizing aromas. These markets are a gateway to the warmth of tradition, providing an intimate experience of European winter festivities.

Pro Tip: Our top hotel recommendations in Vienna and Prague are Park Hyatt Vienna, Four Seasons Hotel Prague, and Augustine, a Luxury Collection Hotel, in Prague. Book your stay using our complimentary Virtuoso Booking Tool and you will automatically receive exclusive benefits, including resort credits, free breakfast, a room upgrade (subject to availability), and more.

Escape to Paradise in Hawaii

When winter’s chill sets in, Hawaii beckons with its tropical embrace and endless summer. Feel the soft sands beneath your feet, swim in crystal-clear waters, and explore the vibrant culture and natural beauty of the Hawaiian Islands. Over the past several years, Team O has made many information-gathering trips to Hawaii to get deep destination immersion, develop expertise in luxury hotel options, and establish valuable relationships with our partners.

The five most visited islands of Hawaii feature a number of luxury hotels and unique sights and activities. Each island offers something a little different in terms of activities and hotels, so you’ll want to pick the right island depending on what you want to get out of your trip. Visit our destination spotlight to view a list of activities and accommodations on each island.

Luxury Accommodations: While there are plenty of 5-star hotels and resorts in Hawaii to choose from, we recently recapped every Four Seasons property in Hawaii on our blog. If you have a specific island or resort in mind and are interested in getting some insight on availability during your desired dates, contact our team and we’re happy to help!

Mexico: Fiesta and Relaxation

If a mix of culture, history, and relaxation is on your winter wishlist, Mexico is the ideal destination. Our blog, “Unexpected Mexico: Ten Surprises From This Beautiful Country“, explores the lesser-known aspects of Mexico as a travel destination, shedding light on its diverse and captivating offerings beyond the conventional tourist spots. It delves into Mexico’s hidden gems, cultural treasures, and unique experiences that extend far beyond the well-trodden path. From vibrant local markets and indigenous traditions to stunning natural landscapes and boutique accommodations, the article highlights Mexico’s rich tapestry of culture, history, and adventure, inviting travelers to discover the unexpected and embark on a journey of authentic exploration in this captivating country.

Pro Tip: Some of our team’s favorite hotels are in Mexico, including Naviva, a Four Seasons Resort, Four Seasons Resort Los Cabos at Costa Palmas, and One&Only Mandarina. Contact our team for availability information.

Snowflakes and Skylines in New York

New York City transforms into a dazzling playground during the winter months, with iconic landmarks aglow and streets buzzing with holiday cheer. Witness the majestic Rockefeller Center Christmas Tree, glide across the ice in Central Park, and be a part of the world-famous Times Square ball drop. Experiencing New York’s vibrancy and festive spirit is a check off the bucket list.

Pro Tip: During the winter, our top hotel recommendations in New York City are The Plaza (any Home Alone fans besides us?), Park Hyatt New York, The Greenwich Hotel, and Four Seasons New York Downtown. You can upgrade your booking to Hotel Plus for assistance with reservations, transportation, and any other activities.

A Winter Wonderland in the Swiss Alps

Enter a realm of tranquility and awe in the Swiss Alps, where snow-draped peaks and charming villages beckon. There’s a reason so many Europeans flock here every ski season. From the elegance of Zermatt to the luxury of St. Moritz, the Swiss Alps offer an enchanting escape for winter aficionados. Delve into alpine culture, savor Swiss delicacies, and explore the pristine wilderness that surrounds you.

Pro Tip: While the scenery speaks for itself and already provides a beautiful stay, there are some luxury hotels that will make your trip even more picture-perfect. We recommend the Grand Hotel Zermatterhof in Zermatt and the Carlton Hotel in St. Moritz.

Unforgettable Memories Await in These Enchanting Destinations

From heart-pounding adventures to serene respites, these top winter destinations promise a symphony of enchantment, relaxation, and joy. Whether you’re skiing at one of the top resorts in the U.S. or Switzerland, wandering through the famous festive markets in Vienna or Prague, or enjoying the vibrant city lights of New York City, there are plenty of destinations to spend your holidays. So, bundle up, pack a swimsuit or winter coat, read our blog on how to plan your trip like a pro, and book your festive holiday to one of these captivating corners of the world.

We have a wealth of inventory of places to stay and things to do in the listed destinations above, ultimately using our Hotel Plus consultative services will help us best tailor your vacation to your preferences. From providing you with consultation resulting in options personalized to your needs to assisting in making arrangements for spa appointments, dining reservations, and transfers, Hotel Plus is designed to elevate the Hotel Only experience.

Already have a trip booked? Worry not! Through a process called a Hotel Reservation Takeover, our team can – you guessed it – take over the hotel reservation and apply our amenities and support your booking from that point on!

  • Complimentary breakfast daily for two
  • Complimentary room upgrade (STA)
  • 100 USD resort credit
  • Early check-in / late check-out (STA)

To get started, email us at or submit a Travel Request Form on our website.

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