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Road Scholar’s Top 5 Winter Getaway Destinations

Say goodbye to the winter blues. Whether you’re a snowbird looking for warmth or have a winter vacation you’d rather spend traveling, there are countless winter getaway destinations you can discover and make new memories. 

At Road Scholar, we offer winter excursions around the globe, opening the world up to explorers like you. In this guide, we’ll go over the best winter getaways, whether it’s the tropical rainforests of Costa Rica or Tanzania’s Serengeti.

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The Best Winter Getaways

Looking for fun places to go in the winter? You’re in the right place. Ditch icy roads and snow flurries for warm winter excursions that allow you to discover new cultures, geography, and cuisine. Take a look at our roundup of the best winter getaways below.

1. Tanzania

Africa is an extremely diverse continent, and Tanzania is just one of the many countries that make this part of the world so unique. In Tanzania, you can find crystal clear waters, one of the tallest mountains in the world, and some of the world’s rarest wildlife. This winter, pack your bags and your finest outdoor adventure gear, as Tanzania will be action-packed.

If you’re looking for warmth this winter, Tanzania is the place to be. During the winter months, Tanzania has average temperatures ranging from 85°F to 95°F. Luckily, you can find yourself on the sandy beaches of Dar el Salaam or the island of Zanzibar. Tanzania is also home to the Serengeti, which is a diverse ecosystem in the northern part of the country where you can do your best to spot the Big Five: the lion, leopard, rhino, elephant, and African buffalo.

Not only are you able to say you’ve seen some of the most unique animals in the world, but Tanzania is also home to Mount Kilimanjaro, Africa’s tallest mountain. If you’re up for a challenge, you can book a hiking excursion to reach the summit, which towers 19,341 feet into the air.

2. Italy

If the scorching temperatures of Tanzania don’t appeal to you, consider a winter getaway in Italy, where winters provide mild temperatures that require a long-sleeved shirt at most. Italy is known for many things—pizza, ancient ruins, coastal waters— you name it. And if you’re looking to experience Italy’s culture and cuisine, the winter is the best time to do it. With fewer tourists, you can enjoy shorter lines and cheaper prices, allowing you to get the most bang for your buck.

If Italy’s calling your name, consider making pit stops at some of these notable cities and towns:

  • Florence: Known for its culture, Florence gives visitors the opportunity to explore Renaissance art and architecture at museums like the Uffizi Gallery and the Palazzo Pitti.
  • Milan: Have an eye for fashion? There’s no better winter getaway destination than Milan, where you can enjoy comfortable temperatures and exclusive shopping, as well as art and history at places like the Duomo Cathedral.
  • Venice: Relax on a gondola as a gondolier paddles you through the narrow canals of one of Italy’s most iconic cities. In Venice, you can view Renaissance and Gothic palaces and marvel at the Byzantine mosaics in St. Mark’s Basilica.
  • Sicily: If you want to spend your winter getaway indulging in comfort food, take a trip to Sicily, where you can learn the time-honored art of Sicilian cooking all while enjoying the notes and flavors of your favorite glass of wine.
  • Rome: History enthusiasts can’t take a trip to Italy without visiting Rome, where you can discover the workings of this ancient city, including its historic rise and fall.

3. Costa Rica

One of the most fun places to go in the winter is Costa Rica. Experience the national motto “Pura Vida” first-hand by relaxing on white-sand beaches and traversing through lush rainforests. This small country makes it easy to escape your winter woes, as you can learn from your expert guide about the exotic wildlife that crawls, runs, or flies through the rainforest, or interact with locals to learn more about what makes this one of the happiest countries on Earth. 

Some of the top things to do in Costa Rica include:

  • Experiencing the Fiestas Palmares in January, which is a two-week celebration with concerts and horse parades
  • Exploring the rainforests in Corcovado National Park or Piedras Blancas National Park
  • Visiting cultural institutions in the capital city of San Jose like the National Museum of Costa Rica and the Museo del Jade
  • Relaxing on tropical beaches like Hermosa Beach and Tamarindo Beach

4. Southern United States

The United States has one of the most diverse landscapes in the world, and wintertime is one of the best times to visit. If you’re looking for a local winter getaway, plan a trip to explore the southern U.S. Unlike its northern counterparts known for frigid temperatures and monstrous snowstorms, the south experiences mild winters, perfect for getting outdoors and discovering local landscapes and geography.

The southern area of the U.S. is home to several notable National Parks, including Death Valley and Joshua Tree National Parks in California, the Grand Canyon, Zion, and Bryce Canyon National Parks in Utah, and the Everglades National Park in Florida. 

In addition to National Park excursions, you can visit smaller cities like Savannah, Georgia, or Charleston, South Carolina, to enjoy some southern hospitality and local history. 

5. Greece

To round off our list of the best winter getaways, we have Greece. There’s no need to worry about surprise snowstorms or frigid temperatures. Here, you can relax by the seaside in coastal villages like Mykonos, Parga, and Pylos. Or, you can venture to ancient cities like Athens and Rhodes where you can learn about Greek mythology and study Neoclassic architecture. 

By visiting Greece in the quieter months, you can enjoy shorter lines at popular landmarks like Acropolis or Parthenon.

Explore Winter Getaway Destinations with Road Scholar

At Road Scholar, we can bring you to some of the top winter getaway destinations across the globe. In our experiential learning groups, you can learn and discover with a diverse cohort to get a deeper understanding of the cultures and traditions around the world. Before packing your bags, review our senior travel tips to get fully prepared and find a travel program that brings you on a winter getaway you’re most interested in.