Best Places to Travel to During Winter Break

The winter months can be cold and dreary, which offers a perfect opportunity to get out of town on a family vacation and explore the parts of the world that enjoy warmer weather in December, January, and February, or perhaps offer the kind of winter wonderland we long for. 

There are many reasons why winter break trips are advantageous. One major advantage is that traveling in winter months in “low season” usually means cheaper accommodations, flight costs, and small crowds.  

Whether you’re looking for an overseas adventure that is warm in winter, like Greece, or taking advantage of being on the opposite side of the equator and going to Australia in December, or perhaps the grandparents want to take advantage of school winter break and take the grandkids on a trip to the Galapagos.

Winter adventures await you and now what is left to decide is where to go for winter break and how to plan it. This is where Road Scholar comes in to save the day. Road Scholar is the authority on educational travel, and winter just happens to be one of our favorite times to go on a learning adventure. We’ve compiled a list of five best places to travel during winter break that are perfect when you are looking for a warm-weather getaway.


In Japan, winter is a slow tourist season, with around 40 percent fewer visitors than during the summer. Japan is a long, narrow country that experiences cold weather in the north and warm Florida-like weather in the southern part.  During the winter months, Japan is a gorgeous snowy wonderland of ski resorts, snow festivals, and hot springs. Kyoto has  17 World Heritage sites and plenty to explore with the geisha district and ancient temples, 

Choose from several Road Scholar’s tours to explore this fascinating city of ancient tradition and beautiful landscape. The epic 16-day Cultural Highlights of Japan will have you experiencing the culture and cuisine while the 17-day Japan Exploration of History, Culture, and Society will include expert-led lectures and field trips. 


There are significantly fewer tourists during the winter season in Greece, which means visitors get to experience life as the locals do during this time. The temperatures are mild in Greece in the winter months in Athens and the islands, while the mountains are cooler and offer 19 different ski resorts. 

For a crash course in authentic Greek Culture, experience Carnival, known as Apokreas in Greek, during the months of January and February. Apokreas is celebrated by Greeks in a nightly ritual of eating, drinking, and dancing. The weekends during Apokreas feature live  music, dance performances, and float parades. 

Check out the best of Greece with the Road Scholar’s nine-day tour, Winter in Greece, discovering the best of this Aegean isle during the quieter winter months when the crowds have dissipated and the weather is mild. Classical Greece will take you on an 11-day tour of Greece from a small ship. 

Costa Rica 

Costa Rica is a biodiverse, tropical paradise that is best to visit on a winter break trip. The winter months, in Costa Rica, are the dry months where rainfall is not as common. The local philosophy and way of life, Pura Vida (the pure life), is contagious because Costa Rica has that laid-back vibe where you can hike active volcanoes, zip line through cloud forests, surf in some of the best surf spots in the world, and mingle with the sloths and monkeys. 

Find your own happiness in December during their dry season and 70-degree weather. Best of all? Some of Costa Rica’s biggest festivals are held in the winter months, allowing you to get a unique perspective on the local culture and traditions. 

Plan your getaway for January to experience the epic Fiestas Palmares: a two-week long celebration with concerts, bullfighting and a traditional horse parade. Or fly down in February to be a part of Envision Music, Art and Sacred Movement Festival, a gathering that hopes to “awaken the self to a higher consciousness in alignment with the natural harmony.”

Road Scholar offers many winter Costa Rican vacations, including Colorful Costa Rica with Your Family and the nine-day tour, A Taste of Costa Rica

New Zealand 

One of the best ways to escape the cold winter months is by traveling to the southern hemisphere. December to February are the warmest months in New Zealand, with temperatures averaging in the comfortable 70s. 

New Zealand is an outdoor wonderland of adventure, from cycling along the Pukaki Ohau canal or hiking up mountains in the Tongariro Alpine Crossing with an expert naturalist. If you enjoy relaxation and wine tasting, there are many vineyards to visit in New Zealand. Nearly one-third of New Zealand’s land is dedicated to national parks, which makes it a playground for exploring natural treasures like harbors, fjords, and snow-capped mountains.

Interested in going to New Zealand in the winter? Road Scholar offers a 12-day trip called New Zealand’s Best: Natural Marvels and Cultural Heritage. Active New Zealand: Hike, Bike, and Paddle the North Island takes travelers on a 14-day adventure trip of a lifetime. 


Spain during winter enjoys more mild temperatures than other parts of Europe, but it's usually sunny, with milder temperatures than most of Europe and not much rain. The Canary Islands off of Spain is said to have some of the best weather in the world, with a constant 24 degrees centigrade. 

What we love most about visiting Spain in the winter months are all of the carnivals from Christmas to Easter Week. Spain offers a great way to feel the festivity of the holidays and learn the traditions of a different culture. In January, Spain celebrates Three Kings Day – when Spanish children receive their Christmas presents – which brings huge celebrations and parades across the country. During winter in Madrid is the Gastrofestival Madrid and Mercedes-Benz Fashion Week. In Barcelona, Drap-Art, Copa Nadal de Barcelona and Fira de Santa Llúcia are huge Christmas markets. 

Road Scholar offers the perfect trip to Spain for anyone suffering from the “winter blues.” Winter in Spain: Culture and History along the Southern Coast explores Spain’s rich heritage, from ancient Roman and Moorish influences to traditional Andalusian cuisine. Winter in Spain: Andalusian Highlights is an eight-day tour of wine, sunshine, culture, and traditions. 

Road Scholar Winter Break Travel

Still don’t know where to go for winter break? Road Scholar aims to provide immersive, educational, and memorial adventure travel for those seeking a warmer climate in the cold winter months.

We have curated tours for those who want warm places to travel during winter break and around the world. Enroll in a warm winter adventure today with Road Scholar!