Top 10 Winter Destinations for 2021 – The Best Winter Getaways

A bunch of people risking their lives on the slopes

As the winter season approaches, it’s time to start thinking about vacation options. A holiday escape might be nice this year, especially after spending last year closer to home–if not completely at home! Likewise, a seasonal getaway to explore a new country or to give cold-weather fitness a try might also be something to consider. (Read more about exercising in the cold in this Project Bold Life story!) And as always, for those in the colder winter climates, thawing out on an island retreat is probably an appealing option. With this in mind, some of the best winter vacations await you this year, and there’s no time like the present to plan! The following list is some of the best winter getaways–no matter what your needs–this upcoming season.

  1. New York City

If you’re thinking about an active destination, certainly the city that never sleeps is a good choice. New York City is always among the best winter vacations, especially around Christmastime. Its seasonal enchantments include the Rockefeller Center Christmas tree, the Rockettes, Central Park ice-skating, and much more. You may even be able to catch The Nutcracker at Lincoln Center. These attractions, along with its exquisite dining and fantastic shopping, makes New York one of the best winter getaways. 

  1. Costa Rica

Perhaps a big city destination is not for you this season. As an alternative, Costa Rica is one of the best winter vacations that offers a nice contrast in many ways. Its misty waterfalls, pristine beaches, and exotic rain forests allow you to immerse yourself in natural surroundings. Likewise, there are an abundance of activities to explore including horseback riding, zip-lining, and hikes. With a quarter of the country environmentally protected, Costa Rica ranks among the best winter getaways for those wanting to get back to nature. 

  1. Anguilla

Just north of St. Maarten, Anguilla is part of the British territories, and is quickly becoming a popular winter destination. Shoal Bay is among the island’s more notable beaches, and it’s lined with soft sand and crystal-clear waters. This, combined with its inherently tranquil setting, is why many consider Anguilla one of the best winter vacations. The island also offers a variety of private resorts to meet every need.  

  1. Prague

While Prague is always a good vacation choice, wintertime is particularly magic in this incredible city. In fact, many who look for the best winter vacations around Christmastime believe Prague to be the best . In addition to its Gothic architecture, history, and entertainment, Prague has Christmas markets in Old Town, holiday caroling, and an abundance of Christmas lights. Plus, the city is known for its sugary pastries, fine wines, and tourist shopping experiences.  

  1. Miami

Miami routinely ranks high on many people’s list of best winter vacations, and it’s there for a reason! If you’re looking to escape the colder climates, Miami’s South Beach offers an incredible respite. If you want an active nightlife, fine dining, and luxury digs, then Miami has you covered. And if you’re into art and music, the city not only has many private venues, but also hosts Art Basel in December and is home the thousands of murals in the Wynwood District.

  1. Valparaiso, Chile

You might not have heard about this coastal town located along the Pacific Ocean in Chile. But if you’re looking for one of the best winter vacations, Valparaiso is worth considering. The town’s 22 hills overlook the majestic ocean and contain an array of pastel-colored homes. For those keen on skiing, Valparaiso is also close to the Andes Mountains. And it’s adjacent to Santiago as well as the Atacama Desert. You can even take a tour of some of the local Chilean vineyards during your time there. Valparaiso’s charm and list of activities are the main reasons it’s ranked as one of the best getaways.   

  1. Breckenridge, Colorado

If you’re looking for a winter getaways that’s still a well-kept secret, Breckenridge isn’t it. This Colorado town that is consistently found on the best winter vacations lists. Not only is Breckenridge close to Denver and Vail, but snow-skiers can choose among four destinations in Summit Valley. Plus, there are dozens of boutiques and shops along Main Street, as well as Breckenridge Brewery, and even a distillery. Nestled in the Rocky Mountains, Breckenridge is certain to provide a perfect backdrop for your winter escape. 

  1. Ilha Grande, Brazil

Ilha Grande lies just outside of Rio de Janeiro in Brazil. Unlike Rio, however, Ilha Grande is much more tranquil and serene, yet still has much to offer. In addition to beautiful beaches and emerald waters, Ilha Grande is surrounded by protected rain forests. It is also home orcas, humpback whales, sea turtles, and even penguins. As one of the best winter getaways, this escape is far from traditional. But its activities and setting will undoubtedly help you understand why it’s among the top places for best winter vacations.

Some people standing beside a giant clock
There are plenty of great winter vacations to be found in the snow–and in the sand!


          9.   Seville, Spain

There are many places in Spain you might consider, but Seville should rank pretty high on your list. As destinations go, Seville has a rich history, and its architecture and culture depict this. In fact, bullfighting, Flamenco dancing, and afternoon siestas are still part of this southern Spanish city’s culture. If sightseeing, unique experiences, and cultural enrichment is appealing, Seville is worth a look. It’s not just one of the best winter vacations, but a good choice for a getaway anytime of the year.  

           10. Turks and Caicos

Island retreats naturally represent a good choice when picking among the best winter vacations. For those tired of the hustle and bustle and the cold, islands provide a perfect recipe for rejuvenation, and Turks and Caicos is one such getaway. It offers not only white sands and blue waters, but also incredible coral reefs that are great for diving.


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