Published November 28, 2025
As the holiday season approaches, many travelers may feel it’s too late to start planning their vacation. However, with a little creativity and the right destination, the options for a memorable vacation are endless. Whether you’re dreaming of a warm-weather escape or a snowy mountain getaway, there’s something for every traveler in this list of exceptional vacation spots.
1. Punta Cana, Dominican Republic: A warm escape
For those who are starting to feel the effects of shorter days and cooler temperatures, a trip to Punta Cana may be the perfect solution. This all-inclusive resort offers a combination of relaxation and excitement to escape the cold. The region is easily accessible from major U.S. cities, making it an ideal choice during the busy holiday season.
Punta Cana’s beautiful beaches, with their soft sand and turquoise waters, provide a wonderful backdrop for a stress-free vacation. It is an ideal location for travelers seeking a quiet retreat and family-friendly accommodation. There are many child-friendly resorts, so families can have fun together. It’s sure to keep the little ones entertained and give adults some time to relax. For those seeking a quieter environment, adults-only resorts offer an upscale experience without the hustle and bustle of younger guests and a more sophisticated and peaceful atmosphere.
2. Jackson Hole, Wyoming: A Classic Winter Wonderland
For travelers who want to experience the holiday season in a more traditional winter setting, Jackson Hole, Wyoming offers a picturesque getaway. Known as a world-class ski destination, there’s more to this destination than just snow-covered slopes. Located at the base of the majestic Teton Mountains, Jackson Hole offers some of the most stunning mountain views in North America, making it the perfect place to vacation.
Jackson Hole’s beauty extends beyond its ski trails. Hike on snowshoes through the vast wilderness or relax in the surrounding natural hot springs. For nature lovers, Jackson Hole is a tranquil retreat where winter beauty takes center stage. With serene landscapes and opportunities for adventure, it’s a destination that promises both relaxation and exhilaration.
3. Lisbon, Portugal: Enjoy the European winter
The holiday season in Lisbon, Portugal is the best time to visit as there are fewer people and travel costs are lower. The city comes alive with Christmas lights and decorations, creating a festive atmosphere perfect for those seeking a European holiday. Lisbon’s charm increases during the winter months, with lively Christmas markets and twinkling lights decorating the streets.
Visitors can enjoy the city’s rich culture by exploring impressive museums such as the Calouste Gulbenkian Museum and the National Tile Museum. These cultural treasures are perfect for those who want to take the time to learn about the history and art that characterizes Lisbon. For travelers who prefer a more natural journey, Lisbon offers plenty of opportunities to stroll through its charming streets and discover new experiences along the way.
Lisbon is the perfect destination for those looking to experience the European holiday season without the crowds common in other major cities. The mild winter climate adds to its charm, making it an ideal choice for those looking for an unforgettable vacation.
4. Chicago, Illinois: Enjoy the city’s festive atmosphere
Although Chicago is famous as a summer tourist destination, it takes on a completely different charm during the winter months. Chicago is transformed into a holiday wonderland, offering visitors a variety of festive activities. Dazzling lights line Michigan Avenue and holiday displays fill the city, creating a magical atmosphere for those looking to get into the holiday spirit.
One of the best ways to experience Chicago during the holidays is to visit Christkindlmarket, a German-style holiday market with Christmas food, drinks, and unique gifts. For those who love outdoor activities, McCormick Tribune Ice Rink offers some fun on the ice. The Willis Tower Skydeck also offers great views of the city skyline, especially for first-time visitors.
Chicago has a number of hotels scattered throughout the city, making it a great option for last-minute trips, with easy access to all of these activities. From exploring Chicago’s vibrant neighborhoods to enjoying iconic holiday events, Chicago guarantees a memorable winter holiday experience.
5. Florida Keys: Tropical Holiday Retreat
For U.S. travelers looking for a warm vacation without the hassle of traveling abroad, the Florida Keys offer the perfect solution. Stretching from the southern tip of Florida into the Caribbean Sea, these islands enjoy warm weather throughout the holiday season, making them a great choice for those looking to relax in a tropical paradise.
The beaches of the Florida Keys provide a relaxing environment perfect for those looking to sunbathe and unwind. But the real highlight of the Keys is the amazing marine life that can be found just beneath the surface. The Florida Keys are home to the only living coral barrier reef in the continental United States, making it a unique destination for snorkeling and diving enthusiasts. Visitors can encounter dolphins, manatees, sea turtles, nurse sharks and have an unforgettable experience in the crystal clear blue waters.
In addition to its natural wonders, the Florida Keys also offers a vibrant nightlife scene, making it an attractive destination for travelers looking to mix relaxation and adventure. Warm temperatures and a lively atmosphere make the Keys an ideal vacation spot for those seeking both adventure and a laid-back vacation.
Conclusion: The perfect winter vacation destination awaits
Whether it’s a beachside retreat, a winter wonderland, or a cultural escape, there’s no shortage of exciting destinations to explore during the holiday season. From the warm sands of Punta Cana to the snowy peaks of Jackson Hole, each location has its own charms and activities that will make your vacation special. The Florida Keys offer a tropical getaway, Lisbon offers a charming European adventure, and Chicago guarantees a festive urban experience. With so many options, you’re waiting to find your perfect winter vacation destination.
