4 Winter Destinations

By caitkontalis | Nov 14, 2020

Who says vacation season is only July?

I love traveling during the off-season. Flights are HELLA cheap, there are less crowds, and I have something to look forward to as the dreary Chicago winter drags on.

Reykjavik, Iceland

Reykjavik, Iceland

Reykjavik, Iceland


Now, this might seem counter-intuitive — but hear me out. Yes, it is cold in Iceland. However, when I went in November it was still warmer than chilly Chicago. PLUS you have the chance to see the epic Northern Lights. My favorite memory of my Iceland trip was eating hot waffles and sipping hot chocolate on a glacier while we waited for the Lights. You can do this on your own, or go with a tour group. I used Reykjavik Excursions. If you don't see the lights on your tour, you can re-book for free for an entire year! It is dark the majority of the time in Iceland during the winter, but when it is light the country looks GORGEOUS because it is consistently the “golden hour”. This makes for the most perfect photo lighting. Also, what's better than soaking in the Blue Lagoon or any of the other hundreds of hot baths around the country than during a winter night?

Amsterdam, Netherlands

Amsterdam, Netherlands

Amsterdam, Netherlands


Amsterdam is a vibrant city. I, again, went over American Thanksgiving because flights were cheeeeeap! The city was filled with people, but I know it was significantly less than if I had gone in June or July. Additionally, the temperature was very temperate in the winter. For late November, I hardly needed my fall jacket. I took a few day trips outside of the city, and there were little traffic and low amounts of other tourists. When I was out and about in downtown Amsterdam, I felt like the other tourists I met were also more experienced travelers as they too were hitting the off-season. I ended up with some of my favorite travel friends during this trip.

Joshua Tree National Park, USA

Joshua Tree National Park, USA

Los Angeles, California


I started traveling to L.A. every January to visit a friend. I enjoy going out there in January so much that it's become an annual tradition. I love L.A. always, but I particularly love it in the winter. It might be because 65–70°F is heaven compared to Chicago around that time. It's generally a bit too chilly for swimming in the Pacific, but if you're a hiking nerd like me — it is the perfect time to go. Every year we've added a different hiking trip to our itinerary and the weather is absolutely ideal for working up a sweat on some Malibu mountain or in Joshua National Park.

Rome, Italy

Rome, Italy

Rome, Italy


Roma in March was absolute heaven. Again, an off-season time meant shorter lines for the classic Roman attractions and absolutely brilliant weather. I'm talking sunny and 75°F every single day. I hardly wore a jacket. As you know, Rome is a huge tourist destination, and visiting in March gave us better and quicker access to a city that would normally be overrun with tourists. Now, the city is bustling so don't think you're walking some empty Pompeii streets. However, you'll find you get a better taste of everyday Italian life when you visit in March. Get up early and watch the nonnas out on their morning walk, the gentlemen setting up their restaurants for the day, and neighbors sharing a cappuccino a the local cafe.

Destination Winter

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Written by cait_kontalis
Hi, I'm Cait Kontalis. Greek-American. Believer that the more people travel, the better global citizens we become.

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