Five Unique Destinations for Winter Holiday Travel

Image: Four Seasons Resort and Residences Jackson Hole, Teton Village, Wyoming. (Photo Credit: Don Riddle/Four Seasons)
Image: Four Seasons Resort and Residences Jackson Hole, Teton Village, Wyoming. (Photo Credit: Don Riddle/Four Seasons)
Phil Cappelli
by Phil Cappelli
Last updated: 7:00 PM ET, Thu November 27, 2025

As the holidays approach, many travelers might think it's too late to plan a memorable vacation. But if you know where to look, there are endless options for travelers looking to escape during the busiest time of the year.

Whether travelers are looking for a warm-weather retreat or a snowy mountain getaway, there is something for everyone on this list of holiday travel ideas.

Punta Cana, Dominican Republic

For people who are feeling trapped indoors as the days get shorter and the weather gets colder, a trip to an all-inclusive resort in the Dominican Republic could be exactly what they are looking for. Flights to Punta Cana are affordable and easy to reach from any major U.S. city, which is attractive during the busy holiday season. 

Punta Cana offers a stress-free beach escape featuring turquoise water and plenty of activities depending on what travelers are looking for. For those who are bringing their kids along, the seaside destination offers family-friendly resorts that will keep the kids entertained and give the adults the relaxation they deserve. And for travelers seeking a quieter, more refined experience, there are plenty of adults-only resorts that provide upscale amenities without the bustle of family crowds. 

Jackson Hole, Wyoming

Jackson Hole offers an entirely different holiday retreat, trading palm trees and beaches for mountain scenery and classic winter snow. This spot is known for its world-class skiing scene, but has plenty to offer outside of racing down mountains.

It is hard to find a more picturesque holiday wonderland than Jackson Hole in the winter. Nestled beneath the Teton Range, the mountain scenery here is some of the best North America has to offer. Travelers can choose to venture out into the cold on guided snowshoe hikes or relax in one of the many hot springs found on the edge of town. If travelers are looking for a holiday travel spot in nature, they should look no further than Jackson Hole. 

Lisbon, Portugal

The holiday season is a perfect time to travel to Portugal, with smaller crowds and cheaper flights that make getting there easy. Lisbon has plenty to offer travelers seeking a festive European vacation.

In Lisbon, the city glows with lights and decorations around the holidays. Christmas markets appear at every turn and provide an opportunity for travelers to shop and explore the city simultaneously. Visitors can also check out one of Lisbon’s many impressive museums, including the Calouste Gulbenkian Museum and the National Tile Museum which are both stunning attractions. Lisbon in the winter is perfect for travelers with nothing planned and want to experience Europe in the holidays. 

Chicago, Illinois

Chicago is known for its summertime appeal, with Cubs games at Wrigley and Navy Pier, but there is plenty to do in the Windy City around the holidays. 

The city transforms in December, with festive lights lining Michigan Avenue and holiday displays around town. Visitors can explore the famous Christkindlmarket downtown and put on their ice skates at the McCormick Tribune Ice Rink. Getting a look at the city from the Willis Tower Skydeck is also a breathtaking sight, especially for those who have not spent much time in Chicago.  A large selection of hotels is spread out around the city with plenty of availability, making it another good reason why travelers should consider Chicago as a last-minute travel spot.

The Florida Keys

Travelers in the U.S. looking for a warm retreat without the hassle of leaving the country should consider planning a trip to the Keys. These islands stretch from the southern tip of Florida toward the Caribbean and feature warm weather during the holiday season.

The beaches in the Keys are cozy and relaxing, but the main star in this area is the marine life that is easily accessible. Visitors can snorkel in the stunning blue water and view the only living coral barrier reef in the continental United States. Dolphins, manatees, sea turtles and nurse sharks are all part of the marine ecosystem in the Keys and can be encountered through snorkeling and diving trips. The warm weather and fun nightlife of the keys are perfect for people looking to get away for the holidays. 


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Jen Mallia

Jen Mallia

Senior Editor

Jen Mallia is an Edmonton-based writer, editor, and Oxford comma apologist. She is a former senior editor of the CAA/AMA Insider magazines and has written for a host of publications, including The Globe and Mail. National Post, The Guardian, Today's Parent, and InStyle. 

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