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The 25 Best Cities For Winter Getaways

Hotels, resorts, tour companies, and airlines all begin to offer discounted tickets and packages for the holidays on Travel Tuesday, which falls on December 3rd this year. 

And, whether you’re interested in heading off for a romantic Christmas amidst snow-capped mountains or are eager to spend the holidays in someplace where the sun shines for longer than a few hours a day, we wanted to rank the best cities for winter getaways. 

In preparation for this hot travel holiday season, we ranked the best winter destinations according to the following criteria:

Pack your bags, set your away messages, and prepare to treat yourself to an early holiday gift. Head to any one of the 25 best cities for winter getaways in 2019 before rining in 2020 in style. You deserve it.

Best Cities For Winter GetawaysHow do these rankings work?

25th. Brasov, Romania

Transylvania is one of the hottest regions in Romania for travellers looking to enjoy the perfect combination of unique historic sites, stunning landscapes, and cosy accommodations. The medieval town of Brasov is the perfect winter destination as it’s just a short bus ride away from Bran where you can visit Dracula’s Castle, play in the snow, and sip on mulled wine.

Transylvania is Top Eastern European Destinations

24th. Guadalajara, Mexico

According to Skyscanner, Guadalajara is one of the best cities for winter getaways in late 2019 and early 2020. The average price for international flights during the winter months is $319, which is nearly $100 lower than flights during the rest of the year. The chance to explore Jalisco, the birthplace of both mariachi and tequila? Sign us up!

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23rd. St. Petersburg, Russia

Russia is one of the best places to travel in February, as many travellers are eager to visit Siberia’s Yamal Peninsula and the local group of reindeer herders. Intrepid Travel offers an exclusive tour that takes travellers from St. Petersburg all the way to the Yamal Peninsula. You can visit the Nenets, a local tribe of reindeer herders.

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22nd. Jasná, Slovakia

If prime powder is what you’re after, then head to the slopes of Slovakia for a fun, adventurous winter getaway in the snow. Jasná is ranked as being one of the best ski destinations in the world. And, since it’s lesser-known than the French Alps and even the Rocky Mountains, there’ll be fewer tourists and therefore cheaper prices.

Slovakia things to do

21st. Tampa, Florida, USA

If you plan on beginning your winter travel journey from a United States destination, then you’ll love to know that Tampa is one of the cheapest cities to fly to in the winter. Average domestic plane tickets cost $236, which is $33 less than they normally are. And, with an average December temperature of 75 degrees Celsius, it’s hard to beat the superb, sunny weather.

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20th. San Salvador, El Salvador

Skyscanner ranked San Salvador as one of the cheapest winter vacation destinations. Prices during winter months are nearly $150 lowers than they are throughout the rest of the year, making December and January a great time to travel to this intriguing Central American city. That’s a great deal in return for getting to experience unique El Salvador Christmas traditions.

San Salvador things to do

19th. Chicago, Illinois, USA

Chicago is pretty cold in the winter, but that doesn’t stop it front being one of the best cities for winter getaways. In part, it’s due to the impressive German-Style Christkindlmarket, which is one of the best Christmas markets in the world. Snowy evenings accompanied by German food and drinks sounds like a great winter getaway to us. Plus, you’ll be able to explore everything else the city has to offer.

18th. Granada, Spain

Parts of Andalucia lie further south than areas of Africa, meaning that travellers in search of sunny weather and warm temperatures can find them both in Granada. Tickets to Barcelona are fairly cheap in the winter, particularly in January and February, and Granada is just a short train ride away. Enjoy the famous Alhambra, tasty tapas, and enchanting flamenco.

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17th. Austin, Texas, USA

Winter is mild in Austin, as it is in other areas of the Southern United States. Fairly mild temperatures combined with stunning Christmas decorations and plenty of exciting things to do make Austin a great place to visit in December. Explore the Trail of Lights in Zilker Park or head to the Blue Genie Art Bazaar with hot cocoa in hand. It’s all enchanting.

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16th. Rovaniemi, Finland

While you’d need to pack some serious winter clothing to enjoy this destination, it’s hard to pass up the chance to travel to the official home of Santa Claus. That’s right, Rovaniemi is the residence of the big man himself, and it’s actually free to visit him. You’ll also find reindeer, lots of powdery snow, and enchanting sleigh rides in the snow. Can winter get more magical?

Best Winter Vacation Destinations in Europe

15th. Grand Cayman, Cayman Islands

Not a fan of cold weather? It’s hard to beat the winter temperatures on the island of Grand Cayman. Crystal clear blue water, scenic beaches, and the chance to swim with turtles all await you here. Plane tickets begin to drop at the beginning of January, making winter break a great time to jet off to this stunning Caribbean island.

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14th. Vienna, Austria

Vienna at Christmastime is straight out of a fairytale. Romantic markets fill the streets of pretty much any town in Austria in December. But, Vienna is particularly enchanting. Classical concerts, elegant balls, and romantic evenings at the city’s famous ice rink make Vienna a delightfully beautiful spot for a winter getaway, especially if you’re travelling as a couple.

Best Vienna Christmas Market in Austria

13th. Abisko, Sweden

The best time to see the Northern Lights is in winter, and there’s no better place to witness this impressive natural phenomenon than in Abisko, Sweden. This city is about as far north as you can get by train, and it’s home to some of the most stunning photo opportunities of the aurora borealis in the world. Husky mushing is another fun once-in-a-lifetime activity you can enjoy if you visit this Swedish city in the winter. It’s as fun as it sounds.

The Best Treehotel Sweden

12th. Oranjestad, Aruba

If you travel to Aruba in January or February, you can snag plane tickets for less than $400, which is a steal for the chance to visit one of the hottest Caribbean islands for 2020. The locals are some of the friendliest people in all of the Caribbean and Eagle Beach is consistently ranked as one of the most beautiful beaches in the Caribbean.

11th. Paris, France

Visiting Paris in the springtime might be every traveller’s dream, but as Ella Fitzgerald once sang, Paris in the winter when it drizzles is just as enchanting. Skyscanner’s research shows that plane tickets to the romantic City of Lights are nearly $200 less than usual if you travel during the winter months. A round-trip flight to Paris for less than $500? What a hot deal.

Paris Hottest Winter Travel Destination in Europe

10th. Hirao, Japan

Hirao is the destination city of the Joshinetsu Kogen National Park. Inside of the famous park is where you’ll find the ever-famous Jigokudani Monkey Park. The local snow monkeys love the heavy snowfall here, which is why they visit the hot springs and lounge around all day. This makes for some great Instagram photos, or even great travel photos if you’re a professional photographer.

Best Cities for Winter Getaways 2020

9th. Birmingham, England

Birmingham is home to the third-best Christmas market in the world. So, it makes sense that it’s a prime spot for international winter travel. People from all over the world flock to the Birmingham Frankfurt Christmas Market. And, the city itself was voted as one of the friendliest cities in the UK. Count on a strong multicultural vibe where you’ll be welcomed with open arms.

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8th. Madison, Wisconsin, USA

Madison might seem a little far north for a winter vacation, but if you travel during December, you can save up to 34% on hotels. It’s an American destination few international travellers seem to think about visiting, but during the winter it can be an enchanting experience and acts as the perfect gateway for day trips to other popular cities.

Best Cities for Winter Getaways in the US

7th. Bali, Indonesia

An average hotel in Bali in December will cost you nearly 30% lower than during peak season. And, while winter might be the rainy season in Indonesia, you’ll still be able to enjoy an average temperature of about 82 degrees Fahrenheit and plenty of sun off and on during the day. Oh, and fewer tourists mean easier access to the island’s awe-inspiring temples, making it absolutely one of the best cities for winter getaways.

Instagram Ubud

6th. Calgary, Alberta, Canada

Google Trends actually ranked Calgary as the second hottest winter destination in terms of hotel pricing. Hotels in December are 36% cheaper than they normally are, meaning you can enjoy a snowy winter wonderland for a fairly cheap price. And, the city serves as the perfect starting point for other winter adventures in the famous Banff National Park.

5th. Pape’ete, Tahiti

According to Google Travel Trends, Pape-ete is the most popular winter travel destination for American travellers this year. While travelling to Tahiti is never cheap, tickets to the capital city of French Polynesia are cheapest from January to May. Natural rock pools, jaw-dropping waterfalls, and lush landscapes await you at this idyllic paradise island.

4th. San Juan, Puerto Rico

San Juan is without a doubt one of the coolest and cheapest winter destinations. Flights are cheapest in January, and you’ll absolutely be able to find fairly-priced vacation packages if you’re interested in going the all-inclusive route. Stretches of white sand, the waterfalls at El Yunque, and some of the most delicious food you’ve ever tasted are all things to look forward to at this hot winter getaway city.

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3rd. Dublin, Ireland

Dublin is one of the cheapest European cities for international travellers to visit during the winter. A round-trip flight from the United States is almost $200 less than the yearly average, with tickets available for under $500. Sparkling snow, charming city events, and the chance to warm up with some strong drinks make Dublin a cosy spot for a quiet winter holiday.

2nd. Heilongjiang, China

If you’re after a winter holiday that’s truly magical, head to Heilongjiang, China. It’s home to the famous Harbin Ice Festival. Last year, it attracted over one million visitors, proving that it’s one of the best winter travel destinations in the world. It’s famously known for its incredible 3D lights shows, but expect to experience a lot of traditional dances and listen to a lot of great Chinese folk songs too.

1st. Zagreb, Croatia

Flights from the United States to Zagreb are the cheapest in February, with savvy travellers able to snag round-trip flights for just $265. However, if you visit in December, you’ll be able to visit one of the world’s best Christmas markets. The whole city is taken over by a Christmas spirit, with an outdoor ice rink as well as lots of trees and lights. Simply put, Zagreb in winter is magical, making it the best city for winter getaways this year.

Elizabeth Thorn
Elizabeth Thorn

Elizabeth has lived and worked in North America, South America, Europe, and Asia, all of which have contributed to her passion for travel writing. When she's not writing, you can find her exploring little hideouts in Colombia or watching photography tutorials on YouTube.

Contact: [email protected]gsevenmedia.com

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